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The Gentleman’s Guide to Transitioning a Friendship Into Romance

The stakes are higher when you want to turn a friend into a lover. Here's how to do it without destroying your relationship

Alex, a 35-year-old tech worker in London, was best friends with his now-wife for about a year before they started dating. “I loved her the moment I met her, but she was due to leave to go back to Canada after her visa ended, so she wasn’t looking for anything but friendship,” he says. “Eventually, though, our relationship became a lot more strained, unspoken and Jane Austen-y — it became clear I wasn’t the only one with feelings.” After a heated argument about a word’s validity during Scrabble, the two ended up shouting, kissing and then sleeping together. “The dam had been breached,” Alex continues. “I still maintain I was right about it being an abbreviation, though.” 

Alex and his wife are proof that it’s possible to transition a friendship into a flourishing romantic relationship, but is it always the right thing to do? Will it destroy the friendship? And what if the sex sucks? Read on for how to decide whether to turn your friend into a lover, and how to follow through if you decide it’s worth pursuing.

Consider Whether It’s What You Really Want

Our culture privileges romantic relationships over friendships, a hierarchy that’s evident in the language we use concerning the transition between the two. We speak about moving the relationship “to the next level” or “elevating” it from a friendship to a romance, or alternatively of remaining “just” friends, suggesting that a friendship is a lesser form of relationship. Especially in the case of opposite-sex friendships — dogged as they are by a cultural script which says they aren’t even really possible — this can result in a pressure to turn a perfectly good friendship into a romance.

But for a whole host of reasons, friendship can sometimes be the best kind of relationship to have with any given person, and the risk of transitioning to a romance that doesn’t work out is that the friendship might not be the same afterwards. It’s therefore worth considering whether this is a risk you’re willing to take, and Mo, a 31-year-old software engineer in San Francisco who has had several romances with friends, says the quality and length of the friendship is relevant here. “The more acquaintance-y friendships can definitely fall off due to awkwardness when you’re finding out whether there’s sexual compatibility,” she says, “but my longer-term friendships have always recovered.” 

Consider the Unique Realities of a Potential Breakup

Breaking up with a person who began as a friend can be additionally painful. As Robyn, a 23-year-old retail worker in England, suggests, you’re more likely to have overlapping or identical social circles, which can be difficult to navigate during conflicts or an eventual breakup. “Bear in mind that bitching to your pals can hold a different kind of weight in this scenario,” she advises. 

Gabrielle, a 30-year-old media worker in New York City, found this out the hard way. Her relationship with a former friend ended in a “messy, sad way” when he cheated with a mutual friend of theirs. “I kind of feel more awful than I would have if he were just some dude,” she explains. “This was a person I trusted and cared for in multiple ways, so it’s not just the normal loss of a relationship, which sucks in its own right, but it’s the loss of someone I already considered to be a confidante.” 

Ask If It’s What Your Friend Wants, Too

This part seems obvious, but even if you’ve considered the risks and want to proceed anyway, you’ll need to establish whether your feelings are mutual — and you should do this with actual words. Even if you’ve drunkenly hooked up, you’ll need to discuss whether it was a one-off incident, or whether your friend is on the same page as you in terms of wanting the nature of the relationship to change. 

Hallie, a 23-year-old violence prevention educator in Chicago who has been in a relationship for two years with a former friend, says checking in with each other at every stage — even if you’ve already got a sexual relationship — is key. “We had a lot of conversations where we discussed boundaries and expectations,” she says, “like, what did we expect from each other from our friends-with-benefits relationship versus how will that change moving into a romantic relationship.”

Trial It With Open Communication 

Once you’re both on board with the idea of giving a romantic relationship a shot, you’ll need to see if it actually works in practice. “Spend more time with just the two of you — as opposed to in a group — to see if there’s a spark,” advises Hailey, a 26-year-old lawyer from North Carolina who was friends with her fiancé all through college. “I’m also a big fan of that cheesy 36 questions thing — it’ll either make your friendship stronger or you’ll both want to make out, and that could lead to romance.” 

If the sex isn’t initially as good as you hoped or there is some awkwardness in the bedroom, it’s worth persevering a little to see if this is just a symptom of the transition. After all, sex often isn’t as good as we hoped it would be with anyone — a Tinder date, a longstanding crush, etc. — and issues can sometimes be resolved by stating your desires plainly and discussing what’s gone wrong in a sensitive manner. The advantage of doing this with a friend is that you’ve probably had to raise difficult issues with them before, and you’re likely to be able to handle the discussion with humor and warmth. 

However, even with the best of intentions, you might find that, as lovers, sex is a struggle, conflict is worse than during your friendship or you have incompatible life goals (for example). You should be able to discuss the possibility that becoming romantic partners isn’t working, and how you might be able to navigate going back to being friends. “It’s really cliche, but honesty and communication is so key here,” agrees Jules, a 27-year-old customer service worker in Georgia who’s in a happy relationship with a former friend. “Let them know that even if they don’t want to date you or vice versa, you still care about them as a friend, so that they don’t feel like you were just using their friendship as a stepping stone to a relationship or hookup.”

For all the potential pitfalls, though, there are plenty of upsides to dating a friend if you’re both on the same page. People who have made it work say that the existing emotional connection, shared history and mutual respect can be a great foundation for a romantic relationship. “While there are, of course, potential pitfalls to dating a friend, the alternative of trying to fit a complete stranger from a dating app into your world is tough,” Mo says. “Overall, I’d say it’s a really underrated way to date in the modern era.”