My Best Friend Is Mad I Hooked Up With Her Ex-Fling

Q: For the past eight summers, I’ve gone to a lake house with a big group of friends. Five years ago, one of my best friends, Ana, brought along a co-worker of hers, Nate, who has become a friend. (They no longer work together, but his best friend is actually now dating another girl in our group.)

Ana used to have a crush on Nate, and they hooked up once that first summer, but he suggested they just stay friends. She was sad about it for a bit, but they have remained close and he still comes on the trips. Now, she has a boyfriend and she and Nate seem fine.

On this year’s trip, I hooked up with Nate. I recently got out of a four-year relationship and Nate is just really fun and flirty. Afterward, I told a couple of my closest friends. I thought it would just be harmless gossip, but Ana was pretty upset about the situation, even though she’s never minded when Nate has dated other people.

The other girls were concerned it would hurt the vibe of the group. I assured everyone it was just a one-time thing — Nate has always been a situationship guy — which smoothed things over, but I felt kind of bummed I even had to do that. Things with Ana went back to normal after a day or so and Nate and I didn’t hook up again after I told him what happened, but we did still flirt.

A few weeks after the trip, Nate invited me out for drinks one on one. I think if Ana finds out, she’ll be upset, and I don’t want to mess up the dynamic of the group, but Nate and I are having fun. And to be honest, I feel like my friends are being a little uptight. We’re all adults — I feel like we should be able to hook up casually without it being a big deal! I’m planning to say yes, but is this a terrible idea?

A: The big question is: What do you actually hope to get out of seeing Nate solo?

While it might seem like Uptight Overkill, I don’t think your friends are shaming you as much as pointing out the potential downsides of continuing to captain the Flirt Ferry. I presume you understand logically that an intra-friend-group hookup changes things, but do you have full appreciation for what that might look like?

Are you ready for one of you to not get the invite for next year’s trip? Are you willing to hurt Ana’s feelings for a second hookup with a guy who thinks dinner is too big of a commitment? A guy who texts you brilliant bon mots like “what’s up” to lay the groundwork for an evening together?

I just have the suspicion that if you’re genuinely looking for strictly a casual hookup, there are better candidates out there. I’m not saying it’s easy to find another bang buddy, but it’s certainly possible. No offense to Nate — who might be a hookup with a heart of gold, what do I know? — but this arrangement doesn’t seem irreplaceable.

And the likelihood is that no matter how casual you try to keep it, things get at least a little awkward when it comes to an end (reminder: casual things definitionally come to an end!).

You don’t need to get permission with Ana or forewarn her about your actions — you are an adult, you’re correct. But please don’t act like it’s silly for your friends to worry about the fallout.

But also, in the meantime, it’s very likely to hurt your friend Ana’s feelings. Should she feel mildly possessive (or whatever imprecise squidgy emotion she feels) over this guy? Maybe not. But I also shouldn’t think I “discovered” Heated Rivalry just because I read it in 2019. We’re all delusional and unreasonable from time to time.

And you can care about — and make accommodations for — someone’s feelings even if you don’t think they’re being reasonable. I think not sleeping with a guy is a pretty low price to pay, all things considered, to not hurt my friend.

You hooking up with Nate is pretty high risk, low reward for the rest of your friends. They aren’t getting to make out in the hot tub together or steal his hoodies when they get cold on the boat. They’re just stuck watching you two “covertly” moon over each other in future group settings, counting down until things get weird and they have to navigate the dynamic delicately. That doesn’t mean you and your happiness aren’t important to them! It just makes a lot of sense why they might not be as gung-ho as say… you… are about this so-called “casual” hookup.

Or perhaps while you’re suggesting it might be casual, a tiny tea light candle-sized flame still burns for the idea this could turn into something more. I don’t blame you. I think pretty much every person ever has been in your kitten heel thong sandals.

I also want to point out that repeatedly having sex with someone you enjoy spending time with can very easily lead to a situation that is Not Casual. Because eventually one or both of you realize, “Hey, we are pretty much dating, so… should we just date…?” If I had a dollar for every time this situation has happened to someone I know, I would be the proud owner of one of those TVs that looks like a picture frame when it’s off.

Of course, often only one person reaches the Obviously We Should Date Because We Basically Are conclusion, while the other is left going, “Huh?” And that is a bummer.

After all this, maybe you’re still thinking about that magical thing Nate does with his tongue, and it’s worth it for you to have a Hot Mess Summer. If you choose to forge forth and cross this randy rubicon, then own it. Make sure you’re being honest with yourself and Nate about what you’re actually looking for. You don’t need to get permission with Ana or forewarn her about your actions — you are an adult, you’re correct. But please don’t act like it’s silly for your friends to worry about the fallout.

I don’t see that many exquisite outcomes when it comes to pursuing Nate. Not because it’s not worth it to take a chance and sleep with a guy after one too many flirty looks across a campfire, but because you already did that, this guy is in your friend group, and because if you’re using this guy to get over your ex and feel fancy-free, do you really want to see him again every year for your friends’ drunken Bananagrams tournament at Lake Winnipesaukee?

I have a strong suspicion it’s not worth bumming out your best friend for a guy with navy bedsheets who forgets to text you back for three days.