Dilemma: I’ve never slept with a guy more than once

When it never goes further than one night, are you doing something wrong? Something you said? Regrettable hookups, straight mate experimentation, and the frenemy that is dating in the digital age…


Ben writes:

I’m 23, a classic young gay millennial – working in the arts, attempting to make the jump to vegan, I learned who Cher was through RuPaul and Mamma Mia 2 (sorry!) – and I’m in a predicament. I’ve never slept with a guy more than once. 

The notches on my bedpost from the last six years are made up of one-night stands from clubs, indulging ‘straight’ friends who wanted to experiment, and random regrettable hookups. 

Over the last 18 months I’ve tried to break this cycle by going on more dates, but something always goes wrong: we end up sleeping together on the first date and regretting it, or he turns out to be a Tory, or they end up disappearing out of my life.

I’ve never had an actual boyfriend, and I’d like something a bit stable. The longest relationships I’ve had were three dates and a bonk. No more. I know I’m not the common factor in this – it’s a recurring problem for young guys my age. Nothing seems to last. It’d be quite nice to have someone to come back hone to. 

There’s a new guy in the frame. I really like him. We’ve danced circles around each other for the last year or so and have mutual friends, so I bit the bullet and asked him out. I really want it to go well, but I also don’t want to over think it.

The Guyliner replies:

So you have everything going for you, plenty to offer, and yet it’s still not happening? Sounds like Cher has hexed you, I’m afraid – she’s not to be messed with and will not be overlooked.

In all seriousness, the problem with wondering why men haven’t seen you again is you cannot possibly know what’s going on in their mind. There could be a hundred different reasons why things didn’t go any further: an ex still on their mind; work issues; the infamous “no spark” – although I can say with confidence the guy you mention in your longer letter who moved countries almost certainly wasn’t emigrating just to get away from you. Young men, especially young gay ones, are complicated creatures. They have self-doubt, baggage, and the awkwardness of their teenage years still hasn’t quite left the building. Plus, they are men, and men are taught not to say what they think, to suppress their feelings. This makes working them out doubly hard because even if you do ask them why things haven’t progressed as you expected, they will lie – either to spare your feelings or desperately hold on to their dignity. Argh.

When we want someone to take us home, we are not ourselves: we say anything to make them like us. It’s like pretending to be into the Killers because the guy you fancy says he is. Is anyone actually into the Killers? Exactly.

To aid the conversion from one-nighter to ride-or-die, you have to go back a bit further and start with your approach. Under what criteria are you selecting your potential partners? Attraction, availability, common ground? The “indulging straight friends” is never going to end well, and while I’m sure they appreciate it, you’re worth more than simply being a rung on their ladder to self-discovery. Meeting guys in clubs doesn’t necessarily have to end in one-night stands only – I’ve known many a friend turn a drunken leer across an illuminated dance floor into a lifelong love affair – but perhaps you’re selling yourself short for that immediate intimacy. When we want someone to take us home we are not ourselves: we can, and do, say anything to make them like us more. It’s like pretending to be into the Killers just because the guy you fancy says he is. Is anyone actually into the Killers? Exactly. During this chatting-up process, it’s likely you may not be totally honest about your expectations, and in turn this might make the guy think it’s no big deal, so he doesn’t have to contact you. Alternatively, he may have been looking for a boyfriend too but isn’t open enough to say.

One of the big problems of finding love is that old frenemy: choice. Thanks to apps, we have all these men at our disposal, and permanency is perhaps thought of as either less desirable or even less achievable. When there are so many options, who’d want to stick around, take a risk on someone? The answer, happily, is loads of people – look at all those gay weddings clogging up your Insta feed – but many of us are reluctant to admit it because of a mixture of entitlement, and the fear of missing out. Surely, if there are all these guys who don’t own a shirt in my neighbourhood, I should try to bang them all, no? Life throws too many “what if”s at us; sometimes we should ignore them.

You don’t say why your hookups are regrettable but my guess is it’s something to do with expectations not being met. Either your criteria are too narrow or restrictive – spoiler: your next boyfriend is very unlikely to have the exact hair colour or body frame you think you’ve convinced yourself you’re only into – or you’re not being honest about what you want. Don’t feel you’re going to scare guys away by being clear you are looking for a fling or a boyfriend; if anything, you’ll scare off the time wasters but I do think there’s a lot to be said for “let’s see what happens”, so long as you keep your goal on sight but don’t destroy yourself if you don’t get there. A need for intimacy is only human, as is the desire for stability and someone to come home to – widen your search criteria, take chances, and communicate. If you want something, you have to ask. Once you encourage a guy to talk, he won’t stop, but it’s a can of worms you won’t regret opening, and once you have, he might just talk his way into being your Mr Right.


Main image: Sony Pictures/YouTube. Buy Call Me By Your Name on DVD on Amazon. The last scene is really good.

1 Comment

  1. Unlike Ben, I’m not 23, far from it in fact. When I was 23 on night encounters, even sleep-overs were rare. Hard to manage. Now many years later I guess if I wanted I could, thanks to a million guys on-line, one night could be every night, (Sydney’s like that). But there’s a price to pay. In the moment all is great. The fun, the chase, the conversation and yes the sex. But as you say good bye, if you want more, and that’s to be expected, you have to work at it. Stay in touch, express your thoughts, express your desires. More often than not the other guy is feeling exactly the same. Don’t hold back. Communicate ask him back, make a date, show you care, be it love or lust or both or just being a nice guy. Nice guys win. (sometime that’s forever).

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