I’m Sleeping With My Best Friend’s Ex. Does That Make Me a Bad Person?

Hello Dr. NerdLove,

I’ve known this couple for about 3 years, and we’ve done a lot of things together through the years. Being their third wheel was never a problem, and I love them both. They were there with me during some of the hardest times of my life in work, dating, or other crises. They were my people, and I always looked forward to the weekends when I’d go to theirs for a movie night, play games, or paint with them. It was the best.

They broke up recently. I had tried to help them through their rough patches, as I’ve been divorced and raked over the coals in dating plenty of times. At the end of it all, they just weren’t compatible. At least not anymore.

Here’s where things got really complicated. These two have been in my life for so long at this point that I didn’t want to just pick a side and abandon the other. They both have requested to hang out individually with me and I’ve obliged. He told me he acknowledges that she and I will get close, and that he’s dating other women and that he’s moved on from the whole thing. Meanwhile, she’s admitted to feelings for me and we did end up sleeping together during a recent hang out.

I feel conflicted. I feel like a snake that played some long con that I never intended to play. She’s such a beautiful person, and we bonded through the years on our love for education, language, art, and our history of the same spiritual practices. It’s made the sex and intimacy otherworldly, and we just physically click in every way we’ve tried. Even our love languages intermingle well.

She’s emphasized that we’re two consenting adults doing adult things together, and that it’s our business, not anyone else’s. I can’t argue with that logic. She’s told me that she’s moved on, that they just weren’t compatible. She seems to understand why I feel conflicted, too.

I guess it’s just that whole question of where is the line drawn? Are we in the wrong for indulging ourselves with each other, and engaging in romance and intimacy together? Have I put myself into a horrible corner that will fracture my social circle? Or, as she’s put it, are we just two adults doing adult things, and that’s our business?

I never felt this way until she and I started spending more time alone together. It just felt different. I just feel like I won’t be able to look him in the eye anymore, and God forbid if he finds out.

I’m With Jesse’s Girl

One of the things I’ve talked about before is how motivated reasoning can be a motherfucker. The issue is that you start from a particular position or have an outcome that you want or expect, and work backwards to justify it. It’s an issue that comes up in dating and relationships fairly frequently; you will see people start from the position that meeting someone is impossible or that women want X or Y and then come up with absurd examples or hypothetical scenarios that are so unlikely that you’d have better odds of winning the Powerball AND Mega Millions at the same time.

Well, that’s part of what you’re dealing with here, IWJG. This is one of those problems that’s only a problem because you’re expecting it to be one and everything is spinning out from there. You’ve created a scenario in your mind were somehow, unbeknownst to you, you’ve been plotting and planning for this exact moment.

Well, let me ask you something in all sincerity: which seems more reasonable to you? That somehow you are secretly Littlefinger, carefully nudging things and biding your time until circumstances lead to you finally getting what you want, or that you’ve been spending time with someone who shares a lot of your values and passions and has a similar background and a mutual attraction has developed organically?

While you mull that over, I’d point out that propinquity – the tendency to start relationships with people you spend the most time with – is one of the strongest and most underappreciated aspects of attraction. Considering that you’ve been hanging out with both of them for a long time and with her on an individual basis since the breakup, I wouldn’t say that this was inevitable, but one or both of you catching feelings to some degree is hardly a surprise. So I think you can give yourself a break on that count.

The next thing I would point out is that getting worked up about this and how your friend would feel is basically denying agency to his ex/your current snugglebunny. She’s hardly a naif or some babe in the woods to your big bad wolf. I have to agree with her on this: you’re both consenting single adults, doing the things that single consenting adults do. This really isn’t anyone’s business, and anyone who has a problem with it are welcome to keep that information to themselves. This includes any busybodies in your social circle who might feel like this is some grand betrayal. They’re welcome to think whatever they want, but their opinions only matter in as much as you allow them to. Relationships aren’t democracies; people can have opinions, but they don’t have a vote.

But even if you weren’t being a snake in the grass this entire time, what about bro code? What about your bro’s feelings? Aren’t you betraying him by being with her?

Well… what about them? I realize this is a stance that gets people annoyed at me, but… yeah, he may be your buddy, but this is no longer any of his business. They broke up. I’ve long said that you can’t call dibs on people and the corollary to that is that there’s also no rule of “I licked it and now it’s mine forever.” The fact that they used to date might – and I stress might – be temporarily awkward, but they are no longer a couple. There’s no more expectation of exclusivity and neither of them has the right to decide who the other can date or sleep with. Even if your bro has opinions about your seeing her, he doesn’t get a vote. The only people who get a say in who she sees going forward is her and the person she’s seeing. Which in this case, is you.

Just as importantly, he’s practically signed off on this hook up anyway. He told you in no uncertain terms that he expected this to happen and that he’s dating other people. He said, straight up, that he has moved on. He may not be standing on the flight deck, guiding you in for a landing but he certainly made it clear he’s not standing in the way either. If he discovers that no, he was only cool with it in the abstract… well, that’s a him problem, not a you problem, and it’s for him to deal with. And hopefully he’s got the emotional intelligence and maturity to recognize that rather than making it something for you to handle.

Will this fracture your social circle? I don’t know. People can get weird about the damndest things. I remember people I know who had an honest-to-god summit in order to hash out a couple’s break up and decide the best way to handle it, who got to stay and who got to go. The key, however was that everyone involved wasn’t even of legal drinking age. I would assume that you all aren’t in high-school and you’ve gotten over high-school drama, but for some folks, high-school never ends.

Should you conduct your affairs (as it were) as though that were the case? Absolutely the fuck not. I could see this being a concern if one or the other person were a monster during the relationship or the way they behaved during the breakup was especially heinous. But from what you’ve said, it was a fairly amicable and clean break: they were compatible until they weren’t and so they ended things. If other people think that it’s wrong, somehow, for a single woman to sleep with a single man simply because they were all in the same social circle, then I don’t know what to tell you except maybe you need friends with more emotional maturity than a high-school junior.

But honestly, nobody’s opinion, mine included, matters here. The only ones that do are yours and hers. You and she have found happiness together and that’s no small thing. Maybe this will be a fling like a comet – bright as it streaks across the sky but gone in the blink of an eye. Maybe this will be a love to last the ages. Either way, you don’t need to borrow trouble from the future. The fact is that right now you and she have something that brings you both joy and comfort; giving that up because of brain weasels and hypotheticals would be a low down crying shame.

Good luck.

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Dear Dr. NerdLove: I am a 45-year-old single woman, also a mom of an elementary school child. I’m pretty good looking, fit, I think I’m smart and funny. I have close relationships with friends and family, and don’t often feel lonely (I’m an introvert).

I honestly think I could be contentedly single forever, and that might be my fate.

However, it saddens me that I never found a person who loved me in that way. It seems… unfair. I’m no better or worse than any of my friends who found love.

While I am aware that I can certainly “get back out there” if I wanted, my concern is that the idea of dating fills me with dread. I dated before and even after I had my child, and had some good times and some not so good. But it was never a joyful experience.

I don’t relate well to men I don’t know at first (I guess I’m shy, you could say). Plus dating is time consuming, and I’d often rather do anything else then spend a week or more texting, then arranging a date, then going out and having the date.

And feeling rejected on the rare occasions I’ve felt connection, hurts more than I think it’s worth.

So the larger winning part of me is content to swear off dating and the possibility of romantic love; I’ll choose to find ways to be happy.

But I guess there is still a piece of me that must want a partner, otherwise I wouldn’t occasionally wonder if I should be dating, or wondering if there really is someone out there that I’m supposed to meet someday, or wondering why I’m a person who wasn’t destined for romantic love.

Do you have any insights for me?

Still Single After All These Years

Let’s start off with something obvious, SSAATY: you are already doing what I tell people they should do if they want to be content whether they’re coupled up or single and that’s awesome. A good life with friends, passions and interests and having your needs met for companionship (and solitude when you need it) is something we should all strive for, regardless of our relationship status.

Now you, as many people who are in that situation, have found that this doesn’t mean that you don’t necessarily want a lover or a life partner; it just means that you have a good life whether you have one or not. And that matters, because it helps keep things in perspective: having someone to share that life with is an enhancement, not a necessity for happiness or contentment or satisfaction.

But here’s the thing about love that I think you need to remember: it’s not about deservedness or fairness. Love isn’t a reward granted by the universe to people who meet certain standards or tick particular boxes. It is, to a certain extent, a matter of probability – a matter of right person, right place and right time all coming together in a particular way. We just happen to take it very personally.

Is it your fate to be single for the rest of your life? Maybe. Or it might not be. Always in motion, the future is, and it’s impossible to say for certainty. You could be hit by a meteorite tomorrow. Or you could meet the love of your life when you’re both 70 and complaining about the quality of the Sunday brunch in your retirement community. Or anything in between. Nobody can say.

What I can say is that if you want love, you don’t have to be treat finding it like you’re planning an expedition to the Congo to find the Mokele-Mbembe. I mean, you can put yourself out there if you really want. You can get on the dating apps, sign up for the single’s run clubs that’re starting to take off, go to speed-dating events or start hitting up cocktail lounges and flirt with strangers if you think it might be fun. But it sounds like you don’t, and that’s fine. That’s not the only way to meet people, especially considering that you know you’re someone who tends to be a slow burn.

Instead, what I would suggest is to just… live your life. But to live it in a way that makes it more likely for you to meet people who you would want to date.

One of the (many, many) reasons why folks often get frustrated with dating is because they treat it like a race, or like you’re interviewing candidates to fill a role. They get hung up on the end point – having A Partner – and so the outcome takes on outsized importance. They have turned Finding Someone into something that becomes more significant than the eventual someone and that can be corrosive to the soul. Yeah, we’ve all heard the cliché of “gotta kiss a lot of frogs to find a prince”, but that still means you’re out in the swamp, planting your lips on a bunch of amphibians. Unless you’re a MILF (Man, I Really Love Frogs), the shine is gonna wear off pretty quickly.

This is why I tell people that sometimes the best way to meet people is to just get lucky… and to understand what goes into making your own luck. Yes, meeting Mr., Ms. or Mx. Right is often a matter of luck. It’s the old saw of luck being the intersection of random chance and preparation, with a better understanding of what that preparation looks like and how to set it up so you don’t sandpaper your soul raw in the process.

The people who are the luckiest in general aren’t blessed by Loki or Tymora or they just happened to have caught Coyote on a good day. They’re the ones who put themselves in fortune’s path – living in such a way that makes serendipity more likely to happen. This way they’re in position to take full advantage when opportunities present themselves.

The easiest way to get lucky without going out and being on the dating market is simply to live your life, enjoy the activities you enjoy and otherwise have a good time in ways that bring you in contact with other, likeminded folks. You’re not looking for your perfect match, you’re just out doing the things you love and, in doing so, meeting people who also enjoy those things.

This may mean gardening clubs or amateur sports teams. It may mean taking conversational language classes or getting a pub quiz team together. Maybe it would involve political organizing or picking a charitable cause to champion. But by spending time doing the things you love and that feed your soul, with other folks who feel similarly, you increase the odds of meeting someone who would be right for you.

And the benefit of this approach is that it’s great for people like you, people who need time to warm up to folks and develop a connection first. Because you aren’t out there Dating – capital D – you don’t necessarily feel the same self-imposed pressure to speed through things. You can get to know people over time, build a connection to them and see how things grow. Someone may seem like they’d be a perfect match on paper and you enjoy their company… but without that pressure to lock things down, you have the time to see whether the chemistry and compatibility is there or if they’re just someone who might make a good friend.

This is, after all, how most people tend to meet their partners. We very rarely start a relationship with a stranger shortly after meeting them; we tend to develop a connection over time. And since you’re not telling yourself that you need to be in a rush, you can take that time to see how things go. If it turns out they’re not right for you, then you aren’t out time that you might have spent elsewhere; they were part of what you were doing already. But if they areright for you, then you’ve had the most amazing bonus to living your life the way you like.

This is why we say that it’ll happen when you least expect it. Not making dating the forefront of your mind means that if and when it does happen, you’ll be pleasantly surprised.

If you take the pressure off yourself to get a particular result and simply live your life in ways that bring you in contact with people who share your interests in passions, you’ll have a much more enjoyable time. It won’t feel the way being On The Market does simply because… well, you’re not. You’re just out and about doing the things you love that just happen to make it more likely for serendipity to happen. And if it doesn’t happen – or in the way you expect – then you’re not out anything, because you still have the rewards of pursuing those passions and ambitions. It’s not quite win-win, but it’s certainly an outcome you’re already satisfied with.

So live your life in the way that brings you contentment and satisfaction, SSATY. Love knows where to find you when it’s time.

Good luck.

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This post was previously published on Doctornerdlove.com and is republished on Medium.

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