As I’ve gotten older, I’ve noticed that my social circles have grown smaller. I can actually count how many friends I text back in a timely fashion on one hand, and I know all my coworkers on a personal level. I surround myself with like-minded people: creatives, writers, directors, and fashion enthusiasts. Most of my activities take place in Brooklyn, where I and most of my peers live, and my dating radius is less than five miles. Everyone I meet seems to share at least one mutual friend. Seriously, anytime I become interested in someone, I look at their Instagram, only to find they’re also followed by this person, that person, and that other person, too. In a few cases, one of my friends might have hooked up with or dated this person. That’s where issues can arise.
As I mentioned, most of my friends live in Brooklyn, and because public transportation in New York can be extremely annoying, a lot of us choose to date people that live in the same borough. No one wants to ride the L train for an hour at 1 a.m. on a Wednesday because their partner lives on the Upper West Side. There have been several cases where my friends are over for dinner and we’re all flipping through Tinder, only to come across at least five guys who another one (or three) of us has matched with before. It’s even more common to see guys we’ve all Noped. I always know there’s a chance that a friend might date or hook up with a past fling and that a new fling might have dated or hooked up with a friend in the past.
A few months ago, I matched with Jake*, 25, a really cool film director. He ticked all the boxes for me — creative, in touch with his emotions, transparent — so I wasn’t going to let him be the one who got away. We texted for a week and then followed each other on Instagram. I noticed he also followed one of my friends but didn’t give it too much thought. But when, after our first date, it was pretty clear that I wanted to see him again, I asked my friend how she knew him. “We hooked up a few times last year, nothing serious,” she told me.
I started seeing Jake frequently, and we continued to have a good time together. Although neither of us wanted a relationship at the moment, we also weren’t seeing other people. My friend, who once swore their relationship was “nothing serious,” became livid. She told all of our other friends that I was dating her ex (which wasn’t entirely true) and made clear that she still really liked Jake*. When the news circled back to me after weeks of not hearing from her, I confronted her about how she was feeling. She plainly stated that my actions were shitty, and I offered to stop seeing Jake if she wanted me to. At the same time, I challenged her about whether she had intentions of getting back with him. After giving it some thought, she told me she was OK with Jake and I continuing to date.
More recently, I dated Nathan*, 28, another film director who I later found out had hooked up consistently with a different friend a few months prior. Immediately after finding out, this friend confided in me that she felt betrayed. “You knew I really liked him” she scolded me, but no, I really didn’t. All I knew was that they were hooking up, not that she was hoping they would become a couple. I was, however, quite clear that as long as I kept dating film directors in Brooklyn, this wouldn’t be the last time I ran into this problem. So I decided to flesh things out with my friend. I convinced her to grab coffee with me, and we talked for hours about how she was feeling, how I was feeling, what we both expected from Nathan. Eventually, we came to the conclusion that it wasn’t a big deal. My friend and I rekindled our relationship, and I continued to date Natahn for a while.
I think it’s totally fine to date and/or hook up with your friends’ former flings, but in the case you do, it’s best to address the situation head on and by asking questions. This gives your friend space to express their opinions and emotions. How long ago was the fling, and how long did it last? Are they still in contact with this person? How would they feel if your relationship with their past fling became more serious than theirs was? Then ask yourself, how close are you to this friend? Do you truly value your relationship? The answers to these questions will guide you, and I’ve found that in most cases, both friends agree that it’s OK to pursue someone’s past fling so long as you keep transparency at the forefront.
Take Rachel*, 26, a friend of mine who is in a thriving relationship with the former fling of her roommate, Jade*, 24. Rachel has been dating Simon*, 26, for a little over a year now. Simon and Jade hooked up a few times but were never serious. After they broke things off, Simon ran into Rachel at a bar, and they really hit it off. Their relationship wasn’t easy at first, and Rachel hid it from Jade for three months by only meeting at Simon’s house. Eventually, she fessed up.
“The conversation was super awkward, mostly because I waited so long to tell — well, actually hid from — Jade,” Rachel says. “So, it really gave off this I know I’m doing something shitty vibe, which could have been avoided if I had just been upfront from the start.”
Jade feels the same way. “My problem wasn’t with them dating, it was more that my roommate was hiding stuff from me,” she says. “It did take time to get over, but I’m totally fine with it now. It also helps that Rachel and I are just roommates. If we were closer friends, I probably would have taken it more personally.”
Dating coach and relationship expert Shan Boodram believes that if your friend is dating your former fling, you should try to make peace with it. “You never [want to] stay in the way of someone else’s connection if that connection is finished for you,” she says. “It’s natural to feel territorial and jealous, but that doesn’t mean that it’s right.” When those feelings do arise, examine them. “Assess where these territorial feelings are coming from and try to manage them,” Boodram says. “You can’t covet everyone, and luckily we live in a world that allows us to meet and move on to new people more easily than ever before.”
I’m not going to let past flings stop me from meeting great people and dating who I want to date. I totally get girl code, and I would never even entertain the idea of dating a close friend’s ex, but when it’s a few-weeks-long casual fling, that’s different. If you’re super social like me and go on a lot of dates, it’s almost unavoidable. So why create a big problem out of it when it’s really fair game?
*Names have been changed to protect innocent daters everywhere.