Mar. 24th, 2026 09:24 pm

Sixmonth

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Yesterday we celebrated our half-year anniversary and it was delightful. We didn't get up to much--I played hooky from work, he made dinner--but we laughed a ridiculous amount. It did me good to see him so happy, especially after how miserable he'd been the day before.

That was partially my fault, of course. The previous week I'd made some reference to being curious about his backstory and he promised that he'd answer all of my questions. Coming up on Sunday, he was so anxious he vomited on the way. I would've been surprised if he'd spent the ride hoping for a train derailment just so he wouldn't have to go through with it.

Honestly though, he story was pretty much what I expected it to be and didn't substantially change my opinion of him. He describes himself as "a good man who's made some terrible decisions" and I think that's accurate. I'm not concerned with the person he was then but rather who he is now and that guy is pretty great.

He's still staying with someone in Naperville to be close to his job there (which he quit only to return to a couple weeks later) and spending two or three nights a week here. It's not a perfect arrangement, but it's working well enough given our moderate level of commitment. (He admitted to me last night that if I called him in the middle of the night asked for help hiding a body, he'd tell me I was on my own.)

He also told me that he doesn't think he'd be able to maintain a friendship if we ever broke up, which makes sense given just how madly he claims to be in love with me. With every passing week, that seems a bit less likely. But, then again, falling in love with Monshu completely blindsided me so who knows what this world has in store for us yet.
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Time for another relationship update!

We're now using the term "boyfriend". Although we're not Facebook Official™, we're official enough that I told my mom the last time I called. Bunj already knew--I let him in less than month into things, swearing him to absolute secrecy. ("You're the only one I've told, so if she finds out, I'll know it was from you.") She surprised me by asking if he'd be coming to her birthday party in January. Sorry, Mom, but I love that man too much to subject him to your family.

I'm kind of torn between settling into something of a pattern--what's even the point of being in a steady relationship if it doesn't come with a certain amount of predictability?--and fighting to keep things from becoming too routine too quickly. We're still mainly doing stuff just the two of us, though we did have a nice double date with Clint and his man recently. And he took the night off again so that he could come to the last cocktail night, where I pressed him into service making drinks. ("Are you putting me to work, sir? On my day off?")

Complicating things is the fact that, not only is he working in the suburbs, but he's living there now too. Tired of the long commute, he got an AirBnB for a month a couple of towns over. When that runs out, he's planning to move in with one of his regulars, who has a mansion within walking distance of the restaurant. He's still eager to spend the two hours on the train to come up and see me, but at some point I expect he'll want me to share the pain a bit.

He says what he loves most about me is that I make him feel good about himself, which makes me a little sad. I told him that what I love most about him is how devoted he is, which kind of annoyed him. I mean, I'm not sure how else to put it. Yes, this is an unequal relationship. He's overjoyed to be dating me whereas I'm just joyed. That's not a small thing! And yet there's no getting around the fact that I've had the great romance of my life already and this is simply gravy. I don't think either of us is nursing any illusions, but it's always hard to say that when things are going well. It's when you hit the rocks that you discover what your deepest hopes and aspirations actually were. I think that losing him would hurt but wouldn't be as bitter as the disappointment around BB, but I could well be completely wrong.

I also have to fess up to a certain amount of FOMO. Naturally I'm looking at the opportunities around me with a bit of chagrin--where were you a year ago! Just a few weeks ago, I met another younger transplant. Chatting him up left me with the impression that he wasn't really into me, but then the next day there was a friend request on social media and, slowly but surely, our messages increased in flirtiness to the point where we're having a date of sorts tomorrow while the AOC is meeting up with an old friend. How many more are there out there like him?

Exclusiveness is off the table for me; I've told him that and he accepts it. But how that actually works in practice is a tricky question. Monshu and I tried out a number of different arrangements and none of them ever worked perfectly. Do I really have the energy for bona fide polyamory? So many unknowns still to navigate.
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Well, WTF.

Sunday he came by and informed me that he'd dropped his phone at work and it was "fucked". Monday he slept away the day and didn't get to it. Tuesday he realised that he could use voice commands and was at least able to send me messages. He came by that evening and we had a wonderful cuddle session. Yesterday I didn't hear from him at all, but he was working. This morning I tried to call and wish him a happy one-month anniversary and got the message:

"We're sorry, the number you have dialed has calling restrictions that has prevented the completion of your call, announcement 19”.

My first though, of course, was that his phone had given up the ghost completely. So I opened the app where we made first contact to see if I could message him there. I couldn't find his profile, something which (as I understand it) only happens if someone has blocked you, not if they delete their account.

Could he have blocked me?

It was an anxious half hour on the shuttle until I could get to work and call him from my work phone. (I actually had to look up how to do that, it's been so long.) I got the same message, which implies that the issue is on his end. What's the next step? I have an address and a place of work. He's not scheduled to work until tomorrow, so I guess I wait until the afternoon and call. If I can't reach him that way, I guess I send a letter to the address?

It's all so weird, I just have to hope it's a dumb failure of technology (and a failure on his part to anticipate this by, say, writing my number down somewhere or looking up my work profile--he knows my full name and workplace--and contacting me there). I even wondered if one of the apparent spam texts I get on a daily basis could have been him; I blocked two local numbers in quick succession last night but when I looked in my phone I couldn't find them.

I'm kind of alternating between being annoyed and hurt. It would not be the first time a man told me all the right things and then ended up abruptly breaking things off. It wouldn't even be the second.
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Oct. 6th, 2025 01:14 pm

Record time

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So, about that boy from Mississippi? Things have progressed to the point where we're planning on having a Serious Talk.

We met up again last week. This time there was a much emphasis on on talking as their was on sex. I even made him a little something to eat. He was deeply impressed by the extant of my booze collection. We must have tasted at least eight different alcohols as we exciting discussed cocktails.

Afterwards he confessed that he was afraid he was falling in love with me. I said I was a little, too, but I didn't see that as a problem. Friday night he happened to be off work and we texted extensively, sharing songs and such.

Then Saturday night rolled around, time for monthly cocktails. I assumed he'd be at work (he bartends in Naperhell) so I didn't invite him, but when he revealed he was free, I insisted he come. I'm not sure why he was hesitant; we didn't really have a chance to discuss that.

I was a little concerned. I tend to be very flirty on these nights and I wasn't sure how he would take that. Also, with Posh Rob back for the first time in ages, there was a real risk that things would turn porny later. He end up spending most of the evening on the porch chatting with a fellow Mississippian so there was no real chance for us to talk.

Fast forward to the end of the evening. The lovely Sikh couple who always arrive late announce they're leaving so it's just me, him, and my pal Mauri on the daybed. Mauri surprises me by announcing he's staying and it soon becomes obvious to me where things are headed.

Now I'm in a bind. I really just want him there, but I don't feel right just telling Mauri to leave. After all, me and MI are just having fun, right? Nothing serious here. So in short order we're all in my bed naked.

I've been through what happened next so many times in my head that I really don't want to hash it all out again (though I'll have to tomorrow), but essentially I had an unexpected attack of jealousy. I got up to pee and remembered there was food out and candles burning, so I went upstairs to see to them. When I got back, they were really going at it and I suddenly felt completely superfluous.

I went upstairs to try to center myself. When I came back down, they were fucking. Now I *really* felt unwanted. In the end, I asked them to leave my bed and when they simply moved to the guest room, I went up and effectively chased them out.

Mauri was very conciliatory. He tried to get me to talk but I was just too upset. The other guy didn't say a word, which hurt as much as anything else, and took Mauri back to his place. I tried to sleep but could barely manage a fitful hour or two before I woke up again.

Finally around noon Mauri reached out and we talked things through briefly. "I'm sorry we didn't notice you weren't having fun." He recognised that he put me in an awkward position. "You can always tell me 'Hey, not this guy'." I know that, but I was trying not to come off as controlling in the moment.

Knowing he was alone, I reached out to the guy. He was very apologetic. Of course he hadn't meant to hurt me. But I still look at his choices and scratch my head. He had so many opportunities to reach out and check in with me and he didn't avail himself of any of them. He just did whatever required the least effort in the moment.

I had a good talk with my best Chilean friend, who suggested that he may just be really conflict avoidant. Together we worked out a game plan for working through things. "Extend him some grace," he told me, and that's what I'll attempt to do. Everyone with me luck
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What else to I come here for besides posting about boys? Time for a few updates!

It's been a banner season since I got back from Seattle. As lovely as that trip was on many fronts, it was really frustrating when it came to cruising. My fresh-meat status meant that I was deluged with offers but sharing a suite with my mother meant there was no real opportunity to act on them (except for the last day, when I took advantage of Mom's earlier departure time to lure a cutie to my room in the last hour before checkout).

I made up for this with a vengeance when I returned. When I look back, one of the striking things is how successful these were. Of the seven guys I was with that first week, I've since been in touch with all but one and I've fooled around with three of them again--all quite different. One is a tall, older, muscled bear who's really into fisting. He wants to take my whole hand, but we'll need a few sessions to get there. The second is a chubby little cub who loves to cuddle. He wanted to go to an orgy last Saturday but felt shy, so I offered to go with him. And then the last kinds of splits the difference: a married short king with amazing equipment who really loves mine. I invited him over expecting a quick session and really got carried away with him.

The same thing happened last night with a new transplant from Mississippi. He looked cute enough online and I budgeted about an hour in order to breed him; after two-and-a-half, I kicked him out so I could wind down and get some sleep. When we finally stopped making out long enough to talk, I found a more interesting man than expected, one who was as comfortable discussing philosophy as he was discussing dicks. I remember thinking "I could fall a little in love with you".

Still trying not to do that, though I am allowing myself to entertain the notion of enhanced FWBs. There's another smart one, a former mathematics grad student now baking bread for Jeff Bezos, who I enjoy talking to as much as I enjoy fucking. We've already had a couple dates of sorts, once visiting a museum and a yarn store together (he's a knitter) and once just canoodling on the back porch of his cohousing in Rogers Park. He's also young enough to be my son, which is bringing out a certain protectiveness as well. We'll see where that all leads us.
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So what am I being a baby about now? Something that happened at the monthly cocktail party last weekend--or rather didn't happen.

To explain, I'll have to go back a month. At the previous cocktail party I was stressed. I ended up inviting too many and the first hour was just me running around trying to take care of everything--making sure there was enough ice, the newbies knew where the glassware was, nobody was trying to open a bottle with a hammer, etc. Eventually, things calmed down and I was able to enjoy myself, but in the meantime I bitched to a lot of people about how annoying it was.

One of them was my new friend Hot David. He suggested I hire someone for next time and I told him that if that's where this was headed then I wasn't interested. I said I would be willing, however, to ask some of the regulars for help. Like maybe assign one of them to keep an eye on the ice bucket, another to make sure recycling wasn't going into the trash, etc. He encouraged me to do this and offered to come early to help out himself.

Flash forward to Saturday afternoon. I sent a message to a chat group with a dozen of these friends (all couples) and Clint in it, prefacing it by explaining how poor Clint was sick and couldn't fulfill his usual duties. At first, I got no response. Then someone asked what Clint had--not because they were concerned about him but worried they might catch something. He replied saying he had a "stomach bug" and one-by-one I watched half of them cancel.

It was deflating to say the least. Oh, and how do I know they weren't concerned about Clint? Because not a one asked what they could do for him, nor has a single one of them inquired about him since. What makes it all the more baffling is that most of them spend these evenings on the back porch anyway and they all know the layout well enough to know that Clint's bedroom and bathroom are downstairs, so their contact would be minimal with him even inside.

I reached out to a friend for support and he basically took their side. I told him I understand that they might have legitimate health concerns, but the fact that none of them asked what they could do without attending (e.g. doing an ice run or something) made their decisions feel awful selfish. (But, you ask, haven't they checked in with me to see if everything turned out okay? Also no.)

We were supposed to meet for brunch this coming Sunday, but you know what? I just don't feel like it. I'd have to deal with them all telling me, "Sorry I didn't come on Saturday BUT..." while I sat there with a sympathetic expression on my face not saying what I actually thought. To hell with them.

Oh the party? A smashing success. I made a point of not mentioning it unless the other person brought it up or had explicitly asked me to remind them and that kept numbers down to a reasonable three dozen or so. I actually got to talk to everyone and even make some fun cocktails and one of the guests took over the kitchen to make some warm appetizers without me wanting to kill him. Hot David made sure someone was answering the door and El Huevón showed up with an extra big bag of ice, despite having spent the entire day getting sunburned at the state fair. You don't need a lot of friends, just the right ones.
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So all the way back in February, I was complaining about the electrician who I thought was becoming a regular thing very much not becoming one. Have we gotten together since then? Not a once. He still texts occasionally to tell me he misses me, and today I finally pointed out to him how insincere that sounds to me when every opportunity he had during the last seven months to choose to spend time with me he chose something else instead.

He took it to heart and acknowledged that--despite the fact that it's been a crazy year for him for a number of reasons--it's ultimately due to his priorities that we haven't spent time together. Which is helpful to hear, but still doesn't do anything about the fact that he hasn't chosen to spend time with me.

What about the last guy I posted about, the one I'd had a couple of enjoyable dates with? We briefly became a thing. But then he came to two significant decisions: the first was that, although he really enjoyed being with me, he ultimately thought we were looking for different things. He still wanted to remains FWBs though, which I considered kind of an ideal situation since I'd independently come to the conclusion that, although I also enjoyed spending time with him and could see us continuing to "date" for a while, I wasn't willing to settle for not being in love with someone I consider a romantic partner. But the second decision was that he needed to move back to Florida for a while and get his life together, so so much for having regular fun times together. His birthday is in 11 days and he plans to come back for that but that may be the last we see of each other for a while.

I did have a good second date with someone last Thursday but it's hard to say how much potential there is there. So I'm back to being awash in sexual partners and bereft of much in the way of romantic prospects, something I have mixed feelings about. Back when Florida Man and I were hooking up a couple times a week and I was starting to bring him to social events, I felt a certain sexual FOMO. But I still feel that would be different if I had someone I was truly crazy for instead of just a solid interesting guy who likes my dick. We may never know.
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I'm coming off a full week of daily hookups and, man, is my penis tired.

It all kicked off a week ago Friday. I was lunching with El Huevón when the smoking hot young guy I was supposed to spend the afternoon with cancelled on me like I pretty much suspected he would. (See previous posts.) I debated looking for a substitute--I was concerned it might lead to invidious comparisons--and ultimately pulled the trigger. I ended up with a cutie I'd been trying to chat up online through various channels for almost two years; it was quite the fun time.

Things only snowballed from there. I picked up someone at the bar that night. The next day, my morning hookup cancelled (again, as I suspected he would) and the guy who made out with me at El Huevón's afternoon gathering slipped away but I scheduled someone else who was also a great way to while away a couple hours. And so on for the new week until Friday came by again and I had a rematch with my previous substitute.

The second time, he stuck around for the rest of the night. We drank on the porch and probably would have gotten horizontal again but I had an Israeli friend in the process of moving arriving in the evening and staying through the weekend. Knowing that was the case, this lovely gentleman kept a respectful distance (though we did manage to hang out for a couple hours on Sunday night) and then popped up on Friday afternoon to stay and spend the whole evening with me.

Reader, I married him.

jk. There's something going on here, but it's too early to say what yet. The sex is fantastic, but we spend as much time in cuddling and pillow talk as we do going at it like frenzied rabbits. We have things in common and we've been talking about what we'd like to do together--hiking in the woods, trying new restaurants, going to concerts, etc. In the course of a week, the paradigm has shifted from "if we see each other" to "next time we get together" and it's a nice feeling that I'm trying to enjoy for what it is rather than force it into some preconceived form.
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So not one, but two reckonings with recklessness lately, and both involving the same bar.

Friday night Daddy Daycare was at 2Bears in Uptown. It was a solid turnout--more than thirty. I showed up early to find Posh Rob sitting in the window with a trio of friends and when I greeted him, he was like, "Your crowd is all in the back." Without us, it would've been nearly empty.

My wingman Marcus and I did our level best to convince the new daddy visiting from "Flarrida" that he should spend some time with us instead of rushing off back to his hotel. When that failed, he headed to SoFo and I set my sights on a new cutie. This one was chatting with my pal Javy so I thought they knew each other. Joining the conversation, I found out they'd only just met. We filled him in on DDC and said we could add him to the list for next time. He said he didn't have any social media, so I offered to take his number and message him.

This was only the first of several lies he told, as I discovered after I let him put his number into my phone. You see, he used his full name, and his unusual surname immediately triggered a memory.

"We chatted on Facebook a while back, didn't we?"

"No, I've never been on Facebook."

It took me a few minutes of searching, but I managed to locate the pics from January 2022. At the same time, since he said he was Berwyn, I asked if he new my pal Jaume who was plugged into the local bear community there if he knew him. He did, and he had little good to say. In fact, he texted back "keep your eye on your wallet, that's the vibe I get". Your man confirmed meeting Jaume at a block party but spun some crazy yarn about why they'd never connected.

If I'd been more sober, I might have heeded these red flags; instead I laughed them off. He was also hitting on my pal Rj and the group was breaking up, so we decided to go elsewhere. Marcus said SoFo was pretty quiet so I convinced them to ride the el with me to Anvil. It was a good crowd; I saw several guys I knew (including the timewaster daddy from last November, but that's another, less interesting story). And the Liar from Berwyn kept flirting heavily with the both of us.

Eventually, I texted Rj to ask if he wanted to team up, but he was like, "You go for it." And I did. A little after midnight, we took a rideshare over to my place and I ushered him into the salon. The sex wasn't good. He looked just as cute as he did in the pictures I'd saved, but in bed he was anxiously switching from one thing to another. On top of that, he was demanding, ordering me around the bed and needing reassurance constantly. He even convinced me to cook him a burger because he hadn't eaten--even though I'd brought him back some gyoza from a visit to the noodle shop across from the bar earlier.

Exasperated, I waited for him to doze off so I could go downstairs and sleep. He woke up and begged me to stay but I insisted. No sooner was I in my own bed but I heard him banging around upstairs, preparing to leave. He came down and got me to say goodbye and we waited awkwardly by the door for his rideshare to arrive.

The next morning, as I was lazing in bed, I saw a string of messages from him and two missed calls. Then I got a message from Jaume telling me he'd heard back from four different friends who'd all had to block this guy because they got tired of his demands. I messaged Rj to fill him in on my night and he told me about how offputting he'd found his behaviour at the bar.

The cherry on top came that afternoon when I was getting dressed for my haircut appointment and retrieved my jeans from the salon. The front pocket felt light; I could've sworn I'd had at least $30 tucked in there. I also noticed that my handkerchief was missing from the back pocket so I looked around and noticed it on the floor. It's extremely unlikely that I somehow took it out and dropped it there, so I think it's quite likely this trick went through my pockets while I was out of the room on some little errand, like peeing or getting him a glass of water.

Fortunately, nothing else appears to be missing. Despite the veritable parade of near-strangers into the apartment over the past few years, this is the first time anything like this has happened. Maybe I've just been lucky. Either way it is a timely reminder to be cautious, pay attention to my friends' instincts, and generally not think so much with my dick.
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So we got off to an odd and unpromising start when I woke up shivering non New Year's Day despite having just slept in a brand-new set of the thickest and warmest flannel sheets I've ever owned. That led to temperature check which led to a COVID test which led to staying home and isolating for two weeks. Then literally my first day back at work, I caught a head cold that knocked me down for several more days. Things went better after that, though I am just getting over a sore throat that threatened to wreck Mardi Gras and Valentine's Day for me.

Not that I had any great plans. Tuesday night, I went over to JR's to see Saltburn so I could finally participate in the discourse. I'd been fascinated with it since the first trailers but I didn't expect it to receive such mainstream attention so I was in no hurry to see it. I did a decent job of avoiding spoilers but they still managed to suck a bit of the enjoyment out of it. Like many, I was also disappointed by the ending, which seemed to undermine the story and the development of the main character, making both less ambiguous and interesting.

This was my second time this year hanging with JR in a low-key sort of way. The first time came after the memorial for ChefBearItalia. I stayed until the end, hoping maybe my friends would invite me back to hang out with them for a bit, but they didn't and I started heading back. Realising that Clint was not likely to be very interactive that evening and not wanting to stew alone, I reached out to JR and invited myself over. We rewatched Barbie, ate a little dinner, I called my mom for her birthday and then went home.

It was exactly the kind of intimate unstructured time I've wanted with him since we first met. The only thing lacking is some physical intimacy. I'm hoping that eventually he'll relax to the point where he'll accept some friendly cuddling. He has gotten better about that in other contexts (such as a friends' Lunar New Year Party last weekend), but I think one-on-one is harder for him. I particularly worry about him becoming touch-starved once his dog passes away, since his dating life is as quiet as it's ever been.

As for my dating life? It's still very unsettled. Once again, none of the possibilities enumerated in previous posts (plus a couple more which had cropped up since then) have panned out. Overall I'm getting pretty tired of folks telling me, yes, absolutely, they do want to get together and then somehow never making any plans, even though I've been guilty of that myself. The closest I've come to a steady thing is my mustachioed electrician, who seems very chuffed that I've taken to calling him "lover" after we've gotten together two or three times. Unfortunately he's signed up for lots of long hours and overtime in order to make the pots of money he needs for the dream house he wants to build, leaving him with almost no time free to drive the hour each way up here to frolic with me.

So against that background, it was pretty crazy what happened yesterday. First, let me introduce Big Dick Down Low Daddy or BDDLD (not to be confused with Big Dick Rick or any other Big Dicks I might have mentioned here). He showed up out of the blue at Daddy Daycare late last November, having been invited by one of our mutuals. To the extent that I have a type which Monshu was the embodiment of, he was a classic exemplar, a burly bearded white-haired daddy with a big smile and roving hands. He convinced me to blow him in the restroom after refusing to give me his number and I impulsively asked him to ditch the Daddies and come back with me, which he did.

It was a lot of fun, though not as much as it would have been if we hadn't both been fairly loaded. Fortunately, we got a rematch the next day when he came back to retrieve the cap he'd left behind. At the time he told me he was usually "one and done" (presumably to avoid getting too attached to anyone). So I'd filed away the bonus session as a fluke owing to unusual circumstances. He mentioned he'd try to come to a future event and I joked about him making his way through our circle of daddy-chasers like a new illness. I didn't abandon all hope of getting with him again, but I didn't consider it especially likely either.

Then, a couple weeks ago, he came down again. I hadn't been feeling great and was planning on a quiet night in when he texted and asked if I was coming to the meetup. My response was swift: "I guess I am now." This time we didn't even make it to the bathroom and I was probably present all of 30 minutes before we left together. I joked that it would have made much more sense for him to stop by on his way into town instead.

So when yesterday I saw a phone call from him (via Messenger, our only channel of communication), I thought maybe he proposing just that. He was actually calling just to tell me that he wouldn't be coming down because he had too much to do before leaving for Florida in a week or so for an extended stay that would keep him away until at least April. So why tell me? Because he saw me comment in the group chat, realised all this, and hoped to rendezvous again in two months. "But I started thinking, I'm kind of a one-sided guy, maybe he doesn't want to see me again."

It was kind of touching, after having so many folks tell me they like me and want to be with me and then not follow through to have someone reverse the script and tell me not to expect anything only to then ask, "We are going to see each other again, aren't we?" Will we? Only time will tell. But it gave me a certain warm fuzzy feeling which set the tone for the evening.

So I didn't really care later when, at the gathering, I saw Useless Fuckboi and he studiously ignored me despite having texted only a week earlier inviting me to get a drink with him (and again afterwards to explain that he "needed time with my friend", i.e. date). And I flirted with the cute boy in the ice cream parlour without any real expectation of it leading anywhere (even though we did spend a chunk of today sexting each other and planning a future session). And I took it in stride when a little cutie showed up at my elbow at SoFo and practically begged me to chat him up. A friend asked me today if all this fleeting attention was making me "jaded". I'm not sure that's the word I'd use. I'm trying to enjoy it without expecting anything to come of it--something I was terrible at in my youth and seem to finally have something of a knack for now. Yay, wisdom of age!
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So today's good-new bad-news is a really doozy. The good news is that, after literally years of trying to hook up with Chef Bear Italia, we finally managed to find time last Wednesday. He came over around 4:30 and we spent a wonderful evening together.

The bad news is that I got a text this morning informing me that he'd passed away in an ambulance on the way to the hospital.

The most upsetting thing for me is probably that it's only a fluke that I even found out. A friend of a friend looked at his mutuals on FB, saw my name, and forwarded me a text from another mutual about his sudden unexpected death. If that hadn't happened, I'd probably have texted him tomorrow or Thursday about getting together again and then just assumed he was blowing me off again when I failed to get a reply.

It's all such an unlikely chain of coincidences that we met at all and managed to stay in touch over 15 years. Our friendship, such as it was, outlasted both of our relationships. And now--just when it was possibly blossoming into something else (he asked me that night if I wanted to date him), it's been cut abruptly short forever.

Just one more reason to hate this stupid month.
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Nov. 29th, 2023 11:53 am

Cuff it

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"Cuffing season" has arrived in the Upper Midwest. This is the time of year when gays supposedly pair up to get through the winter before returning to their whoring ways when the weather gets warm again. It's a term I've been hearing used jokingly for several years but I've never really experienced it myself. But lately? Daaammmn.

So, Saturday night I was hoping to get together with this hot Italian bear who works the Christkindlmarket. Our texts were heading in a good direction and then he just stopped replying. Eager not to sit around feeling like an idiot, I headed out to join a friend who was celebrating his birthday at 2Bears, stopping on the way for "one drink" at the Anvil.

Surprisingly, it actually was one drink, in no small part because I found some cuties out back to flirt with. One of them I looked up on the el ride south and sent a friend request. Almost immediately, he was in my DMs begging for me to do him so we set something up for Sunday evening. When that failed to happen, he asked if we could meet Tuesday evening instead and I agreed, knowing he'd probably cancel.

He did, of course, but in the meantime Hump Day had hit me up asking if I was free. I told him I had tentative plans but I'd keep him in mind, knowing he wasn't likely to try to schedule with anyone else. So when your man cancelled (via a long wheedling text all but begging me to give him another chance this Saturday), I gave it a respectful hour and reached out.

As a result, we had a really lovely evening together. I still don't feel the same way I did before our split over the summer (I tried very hard not to approach things yesterday evening with the mentality that this was a modest substitution for what I really wanted to do) but he did quite a good job of reminding me of the qualities that have always attracted me to him, like his playfulness and eagerness.

When I looked at my phone afterwards, there were 7 or 8 messages from the trans bear I last saw a week ago Friday (who I will henceforth be referring to as "Socks" for my own obscure reasons). He'd first texted about a half an hour into my sesh with Hump Day asking if I wanted to hang out. I initially assumed he was trying to plan something for later but, no, he was ready to hop into a Lyft and show up at my house at 9:30 on a school night for sloppy seconds because "I want you, you weirdo". So if Hump Day had not been available, I would've had an alternative to my alternative.

And that's not all. On Blackout Wednesday, I'd run into two guys I've been trying to get with off and on for at least half a decade, Big Dick Rick and ChefBearItalia. BDR and I had actually been ready to go home together but he was so drunk he got lost trying to follow me out of the bar and I was so drunk I mistyped my phone number, with the result that he sent a naughty text to a complete stranger.

Fortunately, I thought to reach out to a mutual for his number. He hit me back immediately and asked for a picture. This gave me pause, because at least three times now someone has done that and then immediately ghosted me afterwards, but I complied and was rewarded with a promise to find some time after this week.

This got me thinking of the last person who'd ghosted me and I did what I often do--take advantage of the momentary lift of some positive attention to reach out to someone who's disappointed me but I still want. And--to my surprise--this also paid off, with him immediately hitting me back, sending me smut, and telling me he'd also try to find some time for me soon.

Now, while I was outside the bar waiting in vain for Big Dick Rick to come out, I happened to plop down on a bench next to someone I initially didn't recognise. This is ChefBearItalia, who I first met at a house party in Naperhell before Monshu died and seem to run into again roughly every other year. I'd actually seen him at SoFo this summer, sent him a message about getting together, and heard nothing.

So it's not particularly surprising that I forgot all about the encounter until yesterday, when I idly messaged the last number I had on file. Today, about a half hour before Hump Day was to arrive, CBI hit me up on Messenger. He also sounded eager to get together with me sooner rather than later but before we could finalise some plans I had to jump off to answer the door.

When it rains, it really comes down in torrents.

It's flattering, but also a bit overwhelming and perhaps even detrimental. Two or three weeks ago, when I felt like I was putting more effort into this realm than I thought I was getting back, I reminded myself what a mug's game basing your self-esteem on the windsock desires of gay men is. And while I still fundamentally believe that, the lesson risks getting lost in the whirlwind of gay male desire surrounding me at the moment. I'm hoping for some balance soon but right now I just want to enjoy the ride for a bit.
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Over ten weeks ago, I wrote:
Also problematic is Hump Day, who's been MIA for two weeks. Yesterday I reread our old messages and spotted what I think was the problem: I told him about hooking up with with an Ozzie a couple weekends ago. It was just something I mentioned in passing, but from his response it seems like he may have interpreted it to mean that we were dating now and his services were no longer required.

If that's the case, clearing it up should be a simple matter, but I'm kind of annoyed. This is the third time something like this has happened and I'm asking myself "Why?" Why does he assume that I'm so ready to kick him to the curb? I've done what I can over the years to make it clear to him that this relationship is valuable to me without making it sound like I want him to leave his man and yet it doesn't seem to have taken.
I was, of course, utterly correct. He did, in fact, leap to the conclusion that I was dating and "needed space". Clearing things up, however, turned out not to be such a simple matter, mainly because even after he discovered he'd been mistaken he still didn't reach out to me to reestablished ties. He could tell I was annoyed and retreated. Meanwhile, although I continued to reach out to him (sending him greetings on Pride, on July 4th, on his birthday, etc.) I resolved that I was going to wait for him to take action to repair things.

How did that work out? I ended up waiting three months during which I went through a lot of feels. At points, I thought maybe this chapter in my life was closed and that's not such a terrible thing. I took it as an opportunity to explore other avenues. Unfortunately (and unsurprisingly, alas) those haven't really panned out. A couple of times, my longing got the better of me and weakened my resolve but I held firm.

Sunday he finally messaged and invited me to get dinner with him. Well, he invited me to "stop by" and get dinner after; I said just dinner was fine. There was too much that needed to be aired for us to just going back to hooking up like we did before. He agreed and we settled on a place on Argyle.

I wasn't looking forward to it, which may be why I didn't sleep well the night before. That of course only made me dread it more. We hadn't even ordered when he just blurted out an apology. It was exactly what I'd wanted to hear and yet all I could do was stare at the table in silence.

Nevertheless, we had a pleasant dinner, though I was very aware of how my feelings towards him had changed subtly. Did his voice always have that peculiar timbre? Had I actually considered what it would be like to date him? Afterwards he proposed a walk and we headed towards the park, where the Full Moon Jam was underway. We watched that briefly and then I dragged him toward the shore for some privacy.

I don't know that we said everything we needed to but we said most of it. He reasserted that he'd never meant to hurt me and I acknowledged that. He told me that he never wanted to do anything that would impede my search for a long-term partner. I told him to trust me to make decisions about what that entailed and not think he had to make them for me. He talked about the many competing demands on his time and I talked about the strains of being a sidepiece.

Then I proposed make-up sex and we went back to his place and went at it. Was it like old times? Kind of. More than once, to maintain the intensity, I found myself having to push away intrusive thoughts. Hopefully those won't stick around. You don't heal a rift of three months in three hours and things are never the same again because things are never the same full stop. But I put work towards being okay if this turned out to be the end of the relationship and the consequences of that still hold validity.
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What the hell, here's a fun story from the weekend to balance out my bellyaching.

Friday night, Daddy Daycare took place at Farragut's again. The windows were open and there was a big nerdy bearish guy sitting in one of them. As per usual, our group took up the rest of the forward space, from the front wall to the bar. Apparently a couple of our number--including Kayla--attempted to draw him in and got rebuffed.

Finally my buddy CD, the event organiser, came up to me and said, "Someone should make friends with that guy and it should be you." I was two or three whiskeys in by that point (I'd taught the bartender how to make a Boulvardier) and in a very up mood so it was easy to go up to him and ask if he'd been responsible for playing the last three songs on jukebox, all of which had been favourites of mine.

He hadn't, but he advised me that it might have been the bartender. I noticed he had a posh accent and asked if he might be English, but turned out to be a Kiwi from a small town north of Wellington. "Even my New Zealand friends think I sound English." He mused that it might have been due to attending the University of Singapore, where he'd gone to study one thing and ended up majoring in the history of Vietnam. He's now an assistant professor at the university where I work. Well, that did it; as soon as he found out I was in the Library, he asked, "Can't I rant for a little bit?" and went off on what he saw as the flaws in our business model. Happily, they had nothing to do with our behaviour and everything to do with the administration's idiocy.

One by one, my friends drifted away from the bar. Several stopped by the window to say their farewells. The organiser found me and said, with enthusiastic respect, "You're the bear whisperer!" When I checked my messages, I found that Kayla had taken a creeper shot from behind and shared it to a four-way chat with RJ and Clint with the caption "I think everyone in our group tried to engage this guy and failed and this is him and Da after 20 minutes." To introverts like the three of them, this is basically a superpower. Kayla once told me, "You're fearless! You'll talk to anyone." And while he's not quite correct, it's lovely to have my strengths recognised and praised.
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So--in the most predictable turn of events ever--I gave Useless Fuckboi another chance and he blew it. Actually, depending on your accounting, I gave him two more chances. He initially asked to meet Thursday but then around noon he texted asking to reschedule. He told me that, the night before, his estranged ex had tried to break down his door and he'd ended up calling the cops (a story which I accepted at face value at the time but now I'm beginning to doubt). He asked if I was free on the weekend, and I was like, well, I'm meeting my friends at the beach Sunday afternoon and that's right by your place so maybe I could stop by afterwards?

He was enthusiastic; we discussed the idea and made plans. He sent me nude selfies. That morning he texted me "Hi" and I responded "Good morning". Later, from the beach, I sent a cute picture of me and Kayla. No responses. As the party broke up, my friends asked me what I was about and I was like "He has until the bus comes to get back to me." As it turned out, the bus wasn't coming for a while so he had plenty of time to fail to get back to me. I sat in the park next to his apartment building and left a voicemail. Finally, I headed home and fixed myself dinner and a cocktail.

I made the decision not to be angry. Why? What difference would it make? On the ride home I'd been formulating snarky things to say. I was going to congratulate him on using the opportunities I'd given him to cement his reputation as a useless fuckboi. In the end I discarded them all and finally sent a neutral message to the effect of "This seems like self-sabotage to me and I hope you get help." He hasn't responded and I doubt he will. Given how stroppy he was before, I imagine he's found some what to take offence at this. So what; fundamentally not my problem.

The day at the beach, btw, was terrific. The idea germinated the Sunday before when I went there after Greek Fest and was joined by a big red pal of mine who is not Big Red. We decided we needed another beach day and floated the idea in our big gay chat group. Despite a health advisory due to Canadian wildfire smoke, we got a dozen friends to join us including "the children" (Kayla and RJ) and Big Red and his boyfriend. For our friends JIves, it was their first beach day of the entire year.

The weather was great, the water was comfortable (RJ surprised me by going in waist deep with a fraction of the fuss he made last year), and most surprising of all I actually did something sportsbally: We found a fun trio with a floating stereo out on the water and tossed around a spongy little ball for what felt like a solid hour or more. This was especially gratifying because it gave me an opportunity to chat with a cute guy I'd been ogling since he'd arrived a while earlier. That's me--always looking for the next potential disappointment!
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Wednesday's no-show has been pestering me to give him another chance. When I initially said, "Let me think about it", he got all pissy, as if by saying that I was "questioning his character and interest". I mean...yeah? I made the date because you wanted it, but you never texted me to work out the deets, ignored a request to confirm, and ultimately blew me off. But how dare I base my opinion of you on your actions rather than, I dunno, your opinion of yourself? That probably should be my cue to bin him but for the time being I'm still keeping him in the "might be fun to fuck again sometime" category.

Thursday's sushi date went well even though he showed up half-an-hour late due to misjudging the distance via CTA. He kept me updated on his progress, however, and was extremely apologetic, going so far as to make a little bow of contrition when he arrived and thank me for waiting for him. We had a nice chat which ended with him taking back some dinner for his husband, who he brought to cocktails with him on Saturday. All-in-all, he seems worth cultivating even if we never get naked together again.

Friday our intention was to stay in, but someone who used to be a good friend and has been blowing us off for the past year actually accepted a last-minute invite to come over for a drink. When it seemed to be turning out to be just a casual hang, I invited over someone else who I've been trying to get over to my place for two months or so. He was a perfectly decent guest but it doesn't seem like he's into me at all (my friend discreetly withdrew to let us get it on only for this guy to say he was off to Cellblock), which is frustrating but not surprising at this point.
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Pride Weekend has come and gone and I'm left picking through the rubble again on a Monday morning.

For the most part, it was a very positive experience: Gene's rooftop on Friday with the Daddy Daycare crew, followed by SoFo, then BOMB (Bears On My Beach) at Tobey Prinz on Saturday followed by recovery from hideous sunburn, and finally a bear brunch Sunday morning followed by Old People's Pride on Glenwood. Naturally, I saw dozens of fun folks, renewed some acquaintances and formed a few new ones, and generally was a hedonistic gay chad enjoying the best weather Chicago has to offer. But between all the highs were some melancholy moments.

One of these came up on me unexpectedly on the beach. Kayla, RJ, and I had gone to dip ourselves in the surprisingly less-than-hypothermic waters of the lake and were sunning on the sand afterwards. They were supine while I was sitting up and inclining my head to make eye contact while we chatted. Several times, my head was positioned only a couple feet above RJ's and I felt an urge to lean over and kiss him full on the lips--not an overwhelming urge, just strong enough to remind me that I still haven't sublimated all that desire.

I had a quite different moment at Pride North near the end of the day. I'd reached out again to Hump Day after hearing nothing from him for a month and he messaged me to let me know he was there. I traipsed around until I found him, a bit drunk and thirsty, and we stood on the sidewalk embracing each other. But something felt off. Even his scent, which I used to find erotic, mildly repelled me. When I announced that I was going to do a final slut lap, he made an attempt to get me to stay with him but quickly abandoned it; by the time I returned he was gone and I was a little sad but mostly relieved.

Shortly after that, I was around the corner waiting for arepas at the local pan-Latin restaurant, trying to ignore the attention-seeking gay at a nearby table snapping his fan like it was still the first season of RPDR, and sorting through my feelings. I'm tired. Tired of borrowing other men's husbands, tired of seeing happy couples and not being a part of one. (Yes, naturally Big Chick was there with his beau--in matching caftans, no less!) Despite having a couple of dates lined up for this week, there's no sign that this is a mood I'll see the ass end of any time soon.
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Today I'm dealing with the usual event drop after an above-average Mem Day weekend. I'm not exactly sure where to lay the credit for the latter; I guess just the cumulative effect of trying to make better decisions about what is going to give me happiness and satisfaction rather than leading me into anxiety and brooding.

We kicked things off Thursday with the welcome party at Jackhammer. Clint wasn't feeling up to going out so I donned some leather and went over to Randall's alone to pre-game. There I ended up meeting yet another bartender, a charming Lithuanian named Arina, and striking up a conversation with yet another nice straight guy, who introduced me to a peppermint schnapps I actually like. At Jax I immediately ran into a circle of pals from the old Bear Pride days and mostly chatted with them, though I did meet some new folks. It was busy but not too crowded and I found someone fun in the Pit to take home for some good times.

It ended up being a late night so Friday I wasn't up to much. We've still got the issue of demo work being done across the street starting every day but Sunday at 8 a.m. or close to it, so sleeping in is a dodgy proposition. I was a bit at loose ends for what to do in the evening since the weed event at SoFo held little appeal for me. Fortunately a couple of our friends suggested a backyard hang at their new house which I hadn't seen and was eager to visit. It was more beautiful than I'd imagined--and a mere four blocks away!

Around 9 pm I realised I needed food and stumbled over to the chicken fingers place on Sheridan. I was drunk enough that a nightcap at Anvil seemed like a good plan. I didn't really see anyone I knew but I did end up chatting with a lovely Belizean man and getting so distracted that I left my bag behind. Luckily I only noticed this around 11 am, which was right about when the bar reopened, so it didn't ruin my sleep. Clint heard me tearing around the apartment and volunteered to drive me over to look for it. It was, of course, exactly where I'd left it, pressed up against the foot of the bar where the bartenders never spotted it.

To celebrate, he took us to Tweet for brunch and we almost immediately schnagged a deuce on the front patio. Clint was in a rare mood, constantly laughing and singing and generally being a beacon of brightness. He didn't want to drive to the IML vendor mart afterwards so we went back home and switched to CTA. The hotel was chaotic and crowded, but upon arriving at the mart we immediately met a dozen people we knew. One of them, an aggressive Italian, kept demanding ussies and we were happy to slip away to another room for browsing and voyeurism.

Eventually we washed up in the barroom at the north end of the hotel and found a generous bartender who was essentially pouring doubles and charging for singles. At that point, it became pretty clear we weren't going anywhere for a while, but we were both enjoying the atmosphere immensely. Finally as it got late I suggested we head north for some food before going out, which brought us to South of the Border on Morse since the other mooted possibilities were already closed or closing.

Again, we pregamed at Randall's. Again I chatted up an amusing straight boy, this one a graduate of SLU law school. Then we crossed the intersection to Jackie's and saw a line the likes of brought me back to the Bear Pride days. Clint went up front to check whether his pass gave him priority access and it did so he abandoned me tout-de-suite. But the line was very social and I made new friends on all sides during the 45 minutes it took us to crawl to the door. There was a similarly long line for the downstairs so I decided again just to hang in the front bar with pals again. There was a gorgeous Asian bear from Twin Peaks in SF who I tried to bag but though he was very kind I saw his eyes darting all around and decided to make it an early night.

Sunday morning was a little stressed. RJ had planned a brunch in Evanston at 1:30 and seeing that it was after noon and Clint wasn't stirring, I intuited that he was bailing. Fortunately he was still able to give me a ride so I was able to arrive ontime. LeTour is a cute place and we loved the staff. The young bartender was a little flirty and very solicitous and our server was *very* California and made us all fall in love with her a little bit. She also tipped us to an afternoon happy hour with raclette so we'll have to find a time to do that soon.

After dessert at Café Coralie, I got dropped at home to find a mess on the porch with our neighbours fit to be tied from the noisy power washing next door. It made me happier than ever to peace out and head to my powerlifter friends' barbecue steps from the Howard Street Station. As evening drew on, various folks peeled off to head to other locations, mainly SoFo, but I wasn't eager for another late night (which I knew that would probably turn into) and I was enjoying the quiet company so I lingered and lingered.

The next morning, I awoke with a bit of anxiety about having lingered too long. It took me a bit of time to push through that and get myself on the road to Sidetrack, but I eventually managed and found the boys in the atrium. We headed up to the roofdeck just as it started to fill up and shnagged a good table just opposite the bar. It made a good seat of operations from which to run around the bar and I ended up with a lot of new names for my "New People" file, some of whom are local and I'll probably see again. RJ made plans to hook up with an out-of-towner I introduced him to and I'm having my usual mixed feelings about that but I drowned them in a negroni at SoFo after another unsuccessful attempt to dine at Middle Eastern Grill turned into a quick run to Jet's.

I ended off the weekend as it began: With a shot of Ullr at Randall's. I still have some emotions to sort through (probably with the help of Clint's overtaxed ears), but overall a successful time with only a few stressful patches. Could it be I'm finally getting the hang of this?
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So the guy I got hung up on at the tea dance? He sent me a FB request two days later and I just laughed. I considered sending him a message saying "Sinvergüenza!" but I didn't see the point. If I run into him again (what are the chances in this city?) I can say it to his face.

Saturday night I checked out a new bar with Kayla and RJ[*] and they wanted to do Jax afterwards so I got them suited up for the Hole. RJ had fun there for a change, which I was mostly happy about and only the tiniest bit jealous. I ran into two problematic people: One is a cutie that I've been low-key pursuing for a couple of years now. He'll make out with me, get a little bit handsy, and then pull away. I know he has some deep-seated issues so I don't press, but if I'm honest it's all getting a little tiresome.

The other was Big Chick, who once again showed up just as I was preparing to leave--and this despite telling me just over an hour earlier that he was heading home after his shift. He was flirtier than he's been in a while. I told him the story of the tea dance bear, which I described as someone "I'd been working on for an hour", to which he replied "Like you've been trying to work on me. We should talk about that." I told him that's exactly what I'd been trying to do for a month and he finally levelled with me about dating someone else. I asked him why he went home with me if that was the case and he told me they weren't going out back then, which makes sense and accounts for what I've observed. So nice to have some clarity on this even if it means severing the last thread of hope I was clinging to.

Also problematic is Hump Day, who's been MIA for two weeks. Yesterday I reread our old messages and spotted what I think was the problem: I told him about hooking up with with an Ozzie a couple weekends ago. It was just something I mentioned in passing, but from his response it seems like he may have interpreted it to mean that we were dating now and his services were no longer required.

If that's the case, clearing it up should be a simple matter, but I'm kind of annoyed. This is the third time something like this has happened and I'm asking myself "Why?" Why does he assume that I'm so ready to kick him to the curb? I've done what I can over the years to make it clear to him that this relationship is valuable to me without making it sound like I want him to leave his man and yet it doesn't seem to have taken.

[*] The Bear Formerly Known As BB
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Being a man of the world is exhausting sometimes.

Yesterday I headed over to Jax for the monthly non-bear tea dance. It was lovely weather and the place was packed. Among the mostly unfamiliar faces, I noticed one that had stood out to me the night before when I'd visited the bar briefly after my regular cocktails. He'd been prowling the downstairs in heavy denim jacket and I'd considered approaching him but I was kinda tired and kinda done so I just headed home.

If I had, I probably could have taken him home. As it happens, what I ended up doing was procuring him for another. Not intentionally of course--when I chatted him up Sunday afternoon and bought him a drink, I had every intention of getting his digits. But when he casually said to me, "Your friend is very cute," I pretty much knew how things were going to turn out.

The friend is a fellow chaser with highly overlapping tastes and more game than me. I tell folks that I consider him a valuable source of intel. "I've never been anywhere in Chicago where he hasn't been before me," I told a friend earlier in the day. I try not to think of him as competition, but that was sorely tested yesterday as I watched him swoop in and make off with someone I'd hoped to have a little fun with.

The worst part is how it almost wrecked what was otherwise the culmination of a very nice weekend. I even messaged Clint when I got home, dejected, and said, "Tell me to stop being a dildo." I mean, I was literally on my way out the door when a cute guy stopped me, chatted me up, propositioned me, and gave me his number and yet I was moaning about not being attractive enough or whatever.

So I magnanimously sent my pal a text telling him I hoped he'd had a good time. I may even have meant it--why should I begrudge anyone a little pleasure? I even joked that I'd take the drink that the guy "owed" me off him as a finder's fee. I hope we can have a laugh over it next time we're together. And I hope I can kind to the guy if I see him again, even though right now I pretty much want to tell him to go to hell. (Though he already lives in Indiana, which is pretty much the same thing.)
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