So you tried to date your friend and it backfired-here’s how to deal with it

Everyone is always telling me that the best relationships start off as friendships. I hear it from my mom, I hear it from my girlfriends, I hear it from my teachers, my counselors, my coaches, and every once in a while I even hear it from a nosy dental assistant who is way too invested in my (lack of) love life. And I don’t dismiss the theory. It makes total sense that a meaningful, beautiful relationship could bloom out of honesty, laughter, and late night Netflix binges. But the problem, as I see it, is that none of these very well-meaning people address what happens when friend-flings don’t go as planned.

Sure, maybe you’ll kiss your BFF one night and then spend the next 50 years snuggling by the fire feeding each other bonbons and laughing with your heads thrown back in triumph. Or maybe, just maybe, you’ll kiss your friend and things will just get really weird. I don’t have a lot of experience with the bonbon scenario, but I’m kind of an expert on the weird-awkward-oh-my-god-this-was-a-huge-mistake kind of relationship thing. Here’s some things that I’ve experienced and how I’ve dealt with them, I hope it helps to diffuse the weirdness a little bit.

If things just kinda fizzled:

You two were definitely flirting. There were lots of tummy butterflies and winky emojis. Then it just kinda stopped. So what happens now? Do you pretend it never happened? Do you try to reignite it? Do you have a grown-up conversation about what went wrong? The way I see it, how you react depends on where you fall on the flirting and friendship scale. If you’re relatively casual acquaintances who had a brief textual relationship, I’d let it go. Maybe it’ll start up again on its own, or maybe you both just needed a little ego boost. If you were best friends who were on the verge of a relationship, you should probably have a chat (but probably in person so you can avoid the minefield of emojis that got you into this mess).

If you broke it off:

You thought you were into it, but then you woke up one night in a cold sweat and realized that you’d made a terrible mistake. It happens. Sometimes you want something to work so badly you’re willing to ignore all the signs that it’s not a good match. But now what happens? You want to stay friends, but you feel guilty and awkward and you have no idea how to proceed. The best thing you can do is make it clear that you want to stay friends, and then give them some space to figure out how they’re feeling. Hopefully you were kind and gentle in your breakup, and hopefully you’ll both be able to reset and laugh about it in the future over pizza and ice cream.

If they broke it off:

Oof. So everything was going great. You were dating your best friend, just like in the movies! It all felt so destined and right, and you couldn’t wait for your wedding reception where the two of you would show a slideshow of how your love developed from beer pong buddies to lifetime lovers. And then it ended. And now you feel like you’ve lost it all. You want to call your best friend and cry about it, but you can’t because they’re the one who made you cry. The best thing you can do is take some time for yourself. Trying to shift back to being friends before you’re ready can permanently damage your relationship, and burning the bridge completely may lead to regrets later down the road when the pain stops. Maybe you two can be friends again, and maybe not. Either way, it’s important that you take some time to grieve before making a decision on how you want to face it.

If everything suddenly got very confusing and neither of you are sure how to proceed:

The beginning stages of a relationship are very delicate, especially when you’re trying to transition from friends into something more. One weird thing can derail it. I think this is easiest to explain via example. A few weeks ago, I entered into a flirtship with a friend after about a year of romantic tension. Everything was chill, some light party interaction, followed by some flirty texts and date plans. And then: whoomph. Weirdness. Someone (someone who was not me) made an inappropriate joke that may or may not have been a joke and suddenly the tension turned from romance to awkwardness in three seconds flat. And then everything was uncomfortable. I don’t know if it was a joke, I don’t know if he knows if it was a joke, I don’t know if he even knows it was inappropriate. And now we’ve hit what I assume to be a permanent stalemate because neither of us wants to make the tension worse by acknowledging it. Learn from my mistakes. When the weird thing happens, talk about it. If you pretend it doesn’t exist you’ll end up making making an awkward web of weirdness that can only be escaped when one of you moves to another state.

If you wanted different things:

This one hurts. You guys were perfect for each other except for the whole “how you see your futures going” thing. Maybe you wanted to keep things casual, and they wanted a committed relationship. Maybe you wanted kids, and they wanted turtles. Whatever it is, if it’s substantial enough to break you up, it probably for the best. You don’t want to end up unhappy later in life because you compromised on something that was really, really, important to you. You’ll find someone else who shares your life plan, and it won’t hurt as bad.

If you have lots of mutual friends:

Eek. It seemed awesome that you guys had so many mutual friends when you were together, but now that it’s over you have to see your ex/friend/ex-friend at every wedding, birthday, and random party and it sucks. It sucks even worse if you’re put in the position of having to divvy up friends or if your friends are picking sides and drawing lines. The ideal option is to co-exist as civilly as possible and maybe get back to being friends yourselves. The realistic option is that you avoid each other like the plague and make all of your friends very uncomfortable. It’s going to be super weird and super hard no matter how you play it. The most important thing is to not badmouth your ex to your mutuals because it will undoubtably get back to them and then you will feel even worse and look like a bully. Keep it kind, keep it classy, and hopefully everything will sort itself out.

Good luck out there, folks. I hope you find that bonbon love someday, and I hope it’s everything my dental hygienist says it is. Until then, be kind, be mindful, and be cautious about your winky emoji use because they’re highly flammable..

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