Why Aren't You Dating Your Gay Best Friend?

It’s a gay rite of passage. Growing up closeted and surrounded by female friends, someone — usually your mom — is eventually bound to ask: why don’t you date one of them?
Jeff Kasanoff
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May 9, 2025
5
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It’s a gay rite of passage. Growing up closeted and surrounded by female friends, someone — usually your mom — is eventually bound to ask: why don’t you date one of them?

There’s an easy answer, even if you don’t want to share it yet.

But later in life, once you’ve found your community and perhaps formed a tight-knit group of gay male friends, you might be asked the same question… and the answer might not be as obvious.

Because… why don’t you date one of them? One of those total catches you spend all your time with — who share your every interest and whose overlapping sexual histories suggest you’re all in the same league? You know, the ones you’re constantly commiserating with about your hopeless love lives?

Let’s break down the real reasons you’re not dating any of your highly eligible single friends — and whether or not you should reconsider.

Excuses, excuses

At first, the question might seem insulting, even ignorant — akin to your straight co-worker suggesting you’re perfect for the only other gay person they know. You’re not dating your friends because they’re your friends! Not all gay men are romantically compatible!

But that knee-jerk reaction might be a defense mechanism.

So I surveyed some friends, and once they were finished scoffing, I asked them to take a moment and really consider what stops them from dating our moots. Here’s what they said:

“We already dated and it didn’t work out.”

A shocking number of gay besties met on dating apps in the first place. When sparks didn’t fly, they became friends instead, and permanently closed the door to romance.

My take? All that means is things fizzled between two strangers, as they almost always do. And then those two strangers defied the odds and formed a lifelong bond anyway. In my mind, it’s all the more reason to reconsider dating — now that you know how compatible you truly are.

“I’m not attracted to / sexually compatible with them.”

If the thought of touching your friend physically repulses you, fine, that’s a strong reason to steer clear. But if they simply don’t set your loins on fire, good news — that just means you have a head start on most long-term couples.

Initial attraction is always fleeting, whereas sexual chemistry can be built — especially with someone you already trust. Even if you both prefer the same side of the bed, so to speak, a little experimentation can go a long way. And prioritizing sexual compatibility above all is a great way to end up with a virile, absolutely shredded maniac.

“I don’t want to risk our friendship.”

This is valid — in some cases. If we’re talking childhood besties who’ve seen each other through it all, it makes sense to tread carefully. I get not wanting to blow up a load-bearing relationship in your life by, er, bearing each other’s loads.

But if you’re declaring every new friend you meet instantly off-limits, that just means you’re prioritizing  finding new friendships over finding your perfect match. Or that what you’re really afraid of risking is the temporary sting of rejection.

Straight talk

Let’s say I’m right, and dating your gay best friend is a good idea. Why doesn’t it happen more often?

For this, let’s turn to the sacred texts of our heterosexual counterparts. From When Harry Met Sally to Friends with Benefits to The Lizzie McGuire Movie, romantic comedies have forever asked the question “can men and women be platonic friends?” and concluded: absolutely not.

But the common thread in all of them? A ticking clock: a race to the airport, a rushed wedding, the imminent conclusion of an extremely loosely supervised middle school field trip.

The same is true in real life: at least anecdotally speaking, it’s far more common for single straight friends to couple up as they approach 30, and race their biological clocks down the aisle. Think of the cliché: “If we’re still alone by X age, we’ll get married” — as in the other seminal classic, My Best Friend’s Wedding. (Some readers will be horrified to learn the “X age” in that film is 28.)

If two gay men made that pact, what would their deadline even be? With no biological imperative but increasing exhaustion, it’s easy to imagine that fateful day being kicked down the road for decades to come.

In conclusion

So why aren’t more gay best friends dating each other?

In some ways, I suspect they are. See, for many gay men, the most intimate relationships in their lives are with their best friends. They plan vacations, share secrets, squabble over meaningless details together. They even ritually go out on date nights which end in sex — just not with each other.

In other words, they become life partners… all while keeping their romantic options open, because they can. And there’s nothing wrong with that!

But if you’re someone who wants a life partner sooner than later, try this thought experiment: regardless of your current age, imagine you have one year left to pick a partner or end up forever alone. Would you keep rolling the dice on strangers — or might you give a second look to someone you already love and trust?

Don’t get me wrong: gay friendships are something to be treasured. Those connections run deep… which is exactly why they shouldn’t be taken for granted. Who knows? Maybe your go-to plus-one has been the one all along.

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