I Hooked Up with My Best Friend – Help!

Dear Holly,

I’m desperate for advice. I slept with my best friend, and now I think I’ve fucked up our friendship. I’ve been buds with Angela for almost ten years. She actually used to date my brother ( I know, weird eh). Anyway, it’s always been platonic between us, and we actually were roommates for a while too. It’s the only woman I’ve ever had a real friendship with where sexual feelings weren’t involved in some way. We even talk about that sometimes, that neither of us have ever felt that way, and it’s a special and rare find between men and women.

But do you think I could keep it that way? NOOOOOO! I’m feeling a lot of guilt and shame for possibly messing what we had up. I didn’t take advantage or anything. I went over to comfort her because she’d just lost her dog, we had a couple glasses of wine (we weren’t drunk or anything) and she kissed me. It def felt weird, because I think of her as a sister, but things just happened. I slept over, and in the morning I woke up and she had already left for work. She wrote a note: “Sorry about last night. I’ll call you next week.” What do I make of this? What can I do to move forward and smooth things out? – Geoff

Hi, Geoff. I’m sorry you are going through this. But guess what? It’s not uncommon, and I have a good feeling that you can work it out.

I don’t know anyone who hasn’t had sex with a friend “accidentally” at one time or another. When you describe your relationship with Angela as rare, a pure platonic relationship between a man and woman, you’re right. It’s hard to find and harder to maintain. Usually at least one person in the relationship will eventually think about or develop feelings at some point towards the other, and that’s just biology doing its thing.

It sounds like in your case, some emotional wires got crossed when you were comforting. Sometimes grief can cause a strong desire for connection when we aren’t thinking clearly, and then yes, sometimes one thing leads to another.

There’s no doubt she’s feeling awkward about it also, or she probably would have woken you up and not just sneaked out while you were still sleeping. But she did write you a note to say she’d call. Let her be, with her grief and other emotions around what happened between you, and wait for her call. A strong foundation in any relationship can work almost anything out, with honesty and compassion.

What to Do When You Hookup with Your Best Friend

Face It Head On

While it may be tempting to brush it under the carpet, hooking up with your best friend is one of those things that can fester and cause a whole host of weird emotions that will likely erupt down the road.

Be Honest with Yourself

Before you try to hang like nothing happened with your friend, take a good look at your feelings around the intimacy. Did you enjoy it? Do you want it to happen again? Are you worried your friend has feelings that you don’t reciprocate? Know what you feel before you ask how they feel.

Read: 4 Benefits of Being in the Friend Zone

Share Your Truth

Here comes the hard part: Speaking your truth. If you are both on the same page, and you’ve been friends a long time, you’ll have a language that you both understand, and should be able to move forward with, without too much strangeness.

If one of you does want something more than a platonic friendship, it’s going to be challenging.

Read: How to Turn a Friend into a Girlfriend

Make a Decision

If it’s you who wants more and she doesn’t, can you handle that? A lot of men can’t or they do stick around, and it’s the woman who feels weird knowing the truth while trying to pretend it’s not there. If she has shared that feelings have developed and you are interested in someone else, then what?

You both have to do what’s right for your individual well being, and sometimes that means losing a friend. And yes, it sucks.

Read: 5 Tips to Stay Friends without the Benefits

Have a Laugh and Move On

If neither of you wants anything more after hooking up, and you both think it was just a bizarre one-off due to a few too many drinks or external forces like grief, there’s always a chance to just add it to one of your many experiences together, something to bring up and laugh about as you get older.

Maybe you want to transition into a friends-with-benefits relationship. These don’t usually last forever, so that’s something to consider too.

Have you slept with a best friend? How did you navigate moving forward?

Hookup Help is a Q&A series. If you want advice or a woman’s perspective on hooking up, online dating, relationships, or sex, we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter.

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