Hi Jake,
Like a lot of gay men, I’ve always had this fantasy of hooking up with a straight guy. I recently got to make that fantasy a reality while on a work trip to Toronto. He was staying at the same hotel as me, also on a work trip. We first met at the rooftop bar. After a few drinks, we got a little flirty. He said he’d always been curious about being with another guy but hadn’t tried it yet. Next thing I knew, we were in the elevator heading down to my room. My heart was pounding the entire time.
Cut to about two hours later… the sex was terrible. Beyond terrible, actually. Not only was he a super sloppy kisser, but he clearly had no idea what he was doing. About halfway through, I just wanted it to be over. Unfortunately for me, he was having a great time and wanted to keep going and going and going—for what felt like forever. It was hands down the worst sex I’ve ever had in my life.
How about we take this to the next level?
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So now I’m depressed. I spent so much of my life fantasizing about this experience, and now that it’s happened, all I feel is disappointed, unfulfilled, and unhappy. It was so much better as a fantasy. Did I make a mistake by doing this? Am I being ridiculous for caring so much?
Straight Up Disappointed
Dear Straight Up Disappointed,
First of all, thank you for living out this fantasy so the rest of us don’t have to. Consider it your gay public service. 🙂
Seriously, though, what you’re feeling makes total sense. You finally scratched a long-standing itch, and instead of satisfaction, you’re left feeling bummed out and disillusioned. That kind of emotional whiplash is tough, especially when something you’ve built up in your imagination for years turns out to be… a sloppy himbo clearly in over his head.
Here’s the thing about fantasies: they’re perfect because they’re not real. In a fantasy, the straight guy is always just the right amount of curious. He kisses like a god, knows exactly how to touch you, and maybe even surprises himself with how into it he is—because after all, you’re the embodiment of every repressed fantasy he hasn’t quite admitted to himself. You feel wanted and special. And none of it involves awkward fumbling, bad technique, or post-coital regret.
But real people aren’t fantasy characters. They’re messy, inconsistent, and sometimes painfully unaware of how inexperienced they are. So when fantasy meets reality, something’s gotta give—and often, it’s the fantasy that breaks.
Now, does that mean you made a mistake? Not necessarily. I think it means you’re human. You acted on a desire that was alive in you, and even if the result was disappointing, you gave yourself permission to explore. That’s not a failure—it’s data. You learned something important about what you want, what you need, and maybe even what turns out to be a total letdown once it leaves your imagination.
You also bumped into a deeper emotional truth: sometimes we tie meaning to these bucket-list experiences. We assume the fantasy-fulfilled version of ourselves will feel more complete, or validated, or sexy. And when that doesn’t happen, it can be a quiet kind of grief—like saying goodbye to an old story we didn’t realize we were still telling ourselves.
So no, you’re not ridiculous for caring, and you’re not wrong for wanting it to feel more magical than it did. And you’re certainly not alone in discovering that some things are better left in the fantasy file.
That said, this doesn’t mean all curious-straight-guy encounters are doomed. But it does mean that if you try again, it might be worth going in with less romanticism and more curiosity—about him, about yourself, about what might unfold when you don’t already have a script in your head.
One more thing: if at any point an encounter isn’t satisfying, you have every right to pause and say, “I’m just not feeling this.” You don’t have to suffer through bad sex out of politeness, hope, or momentum. Your body and your time are yours—and if something isn’t working, you’re allowed to speak up without apology.
In the meantime, don’t beat yourself up. You’ve got a great story—even if it wasn’t the one you expected. And let’s be honest: most people never get to check this box, even though it’s one of the most common fantasies out there. You lived the dream and braved the trenches. It wasn’t sexy, but it was service—with your message hopefully sparing countless others the same disappointment. On behalf of the community, we salute you.
Ask Jake is our advice column by Queerty editor and Licensed Marriage & Family Therapist Jake Myers. If you have a question for Jake, email [email protected], or connect with Jake even deeper through his LGBTQ therapy platform.
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