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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.
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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