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You Want to Date Your Best Friend. But Should You?

There are plenty of reasons why dating your best friend seems like a good idea, particularly if you’re feeling burnt out on dating apps and sick of meeting strangers you don’t end up clicking with. With your best friend, you already have some necessary building blocks for a romantic relationship: You get along swimmingly; you know how best to communicate with one another; you likely share similar values and interests; you know what infuriates them and how to cheer them up when they’re having a rough day. You also have insight into their past sexual and romantic history—assuming you share that stuff with each other, because you’re best friends.

But of course, there’s one huge risk when it comes to dating your best friend: What if things don’t work out? If you break up on bad terms, you won’t just be heartbroken; you’ll also have lost your best friend—the person you’d typically turn to when you’re going through relationship problems.

That risk shouldn’t necessarily stop you from dating your BFF if it feels right. But before you take that next step or not, there are some things you need to consider. To learn how to take a more calculated risk when thinking about dating your best friend, we spoke to two relationship experts: sexologist Marla Renee Stewart, MA, and Kevin A. Patterson, M.Ed., author of Love’s Not Color Blind.

Don’t just do it out of convenience.

After the hellscape of 2020, it’s normal to feel lonely, sad, and in desperate need of physical intimacy and human connection—but those things alone aren’t valid reasons to date your best friend. If you’re going to date your BFF, it has to be because you want them, specifically, and not just because you’re trying to fix a you problem. “Dating someone out of convenience is not fair to them, and if it’s your best friend, you want to make sure that you come at them in an ethical and compatible way,” Stewart says.

Patterson adds, “The world is in a strange place due to the pandemic, and we’re not all in our normal frames of mind.” So he suggests evaluating “where the change from ‘friend’ to ‘partner’ is coming from.”

Think about whether they’re friends with their exes.

If they are friends with at least some of their exes, this is a good sign, Stewart explains. If you were to break up, “There is hope that you two could resume your friendship again after a period of healing,” she says. However, if they are not used to being friends with their exes, “Then you can probably expect to not return to a place of friendship once you move into the dating category.”

You need to do some self-examination, too. Think about whether you’re friends with your exes. If you aren’t friends with any of them, then be skeptical of whether you’ll be able to return to a place of friendship if things go south with your bestie. Could you live without this person in your life?

If you are friends with your exes, think about the type of friendships you have. Are you super close, or is it more of a “we’re cordial in a group setting” dynamic? The thing is, even if you can return to a place of friendship after you date, it’s unlikely that your friendship will be the same as it was before. Be prepared for that change.

Casually gauge your friend’s feelings about the idea of dating friends.

If your crush on your friend is real (as opposed to a matter of convenience), and it seems like you’d both be open to staying friends should things go south, then your next step is having a casual talk about sleeping and dating friends—especially if this is something you haven’t spoken about before.

“The fact is, some of us like to have sex with [and date] our friends and some of us don’t,” Stewart says. “So it’s worth investigating what kind of person your best friend is.”

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Of course, you need to have a tact when bringing up these topics. You can’t ask them out of the blue, “So, theoretically, would you date your best friend?” If you do that, they’re gonna know you’re into them. Perhaps you can frame the conversation by talking about previous friends with benefits you had. Or you can say you were reading something about COVID cuffs and heard people were settling down with friends to have a romantic partner during the pandemic.

Have they attempted to date a friend in the past? How did it go? Do they have a policy of never hooking up with friends because it gets too messy? If you don’t like what you hear, then you probably shouldn’t attempt to date them.

Consider that your friendship might already be in danger.

While the biggest concern with dating a BFF is that you’ll damage your friendship, Patterson notes that your relationship “is likely already in danger” if you really like your best friend romantically. In that case, “better to shoot your shot and chance making it a bit awkward than to not shoot your shot and spend the rest of your life wondering ‘What if?’” he says.

Patterson adds that friendships break down all the time. “I’d rather it be because we tried for more rather than some other collapse that might be outside our control.”

At the end of the day, we can’t make this decision for you. Only you can do your research and make this choice for yourself. Good luck.

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