Go Ahead and Date Your Friends, But Break Up Well

Green background with this text in black letters "Computer dating's OK, if you're a computer. -Rita Mae Brown"
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It’s a common rule that a lot of people have when they open up their relationships: No friends.

It’s likely one of those carryovers from traditional dating wisdom. Don’t date friends because most relationships break up, and if you break up with someone, you’re likely to ruin the friendship.

But my dirty secret: I nearly always date friends. And if I run into trouble, it’s usually when I deviated from this practice. I wrote about it a little in an earlier piece, “Why I’m (Nearly Always) Friends First.”

In fact, there’s a conflict between 2 standard pieces of dating advice:

  1. Be friends first.
  2. Don’t date friends because most relationships break up, and if you break up with someone, you’re likely to ruin the friendship.

So we’re expected to go on the hunt for new friendships, build those new friendships up until we’re satisfied that it’s time to pursue a relationship, and expend them if and when the new connection goes south?

Um.

Why not just date people we’re naturally friends with? People who know us already. And then… break up like decent human beings. Rather than cultivating a new crop that we’re ultimately going to treat as expendable.

Because that’s what really ruins the friendship: Not dating them in the first place but breaking up with them in a way that damages the relationship.

Is it possible to break up civilly? You betcha.

In fact, learning to break up well might just be one of the best skills you can master.

Ditch the Unhelpful Breakup Scripts

We’re up against some profoundly unhelpful cultural scripts surrounding breakups:

  • That they’re bad in and of themselves.
  • That we should avoid them at all costs.
  • And that there’s a good person and a bad person in every breakup.
  • That there must be a winner and loser in the court of public opinion.

No, no, no, and no.

It’s Not You, It’s Not Me, It’s Us

More than anything, relationships live and die based on compatibility. It’s about the combination of the people involved and how that either works. Or doesn’t.

And it has to work unanimously, for everyone.

For issues with basic chemistry, this can be addressed simply with something like, “There’s nothing wrong with you. You have a lot of great qualities. But for some reason, I’m just not feeling it.”

Or if there’s some kind of dealbreaker, point out that incompatibility. I had one ex-girlfriend who wanted more control over my social life than I could have ever lived happily with. And even after multiple redirections and in-depth talks about it, she would not be dissuaded. She had expectations of me and of our relationship that just weren’t what I wanted.

It became evident that this wasn’t going to work out.

Could I have flipped out on her and told her that she was controlling? Neurotic? Unfair?

Sure. And when I was at my wits’ end, I was sorely tempted.

But on the other hand, someone else might want that kind of relationship. To them, it might signal caring and concern.

So I instead focused on the fact that we wanted different things.

But Wait — Doesn’t It Take Two to Break Up Well?

One thing to keep in mind, however: It takes two to break up well.

Well, great.

Doesn’t that throw the whole thing out the window?

Can we ensure a decent breakup when we can’t control both sides of it?

Ensure? No.

But make it more likely? Yes.

And this is where dating people you already know fairly well can be a boon. Because you get to see how they react in similar situations.

Observing How Well They Deal with Rejection

The key factor in whether it seems like we could break up well is how well someone deals with rejection.

How do they deal with rejection? Are they resilient? It’s fine to be temporarily discouraged by it. And lick their wounds before eventually moving on.

But if they demonize everyone that criticizes them, if they just can’t seem to let things go, and if they have a hard time getting over rejections (whether personal or professional), then it gives me pause.

Now, it isn’t like I continually scan my friends group, ranking them in order of how well they deal with rejection, and selecting partners solely based on who seems like they deal with rejection best.

Instead, after I’ve discovered I’m attracted to a person, how well they seem to deal with rejection is part of my decision whether or not I decide to pursue that connection and actually date them.

Because I don’t kid myself that I’m going to magically deviate from their normal way of dealing with people.

And that’s one prime reason why it’s helpful to date friends. You get to see how they typically behave with other people (when they’re not trying to impress anyone) before taking the leap yourself.

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