Casual Dating

Should You Date an Ex-Girlfriend or Hookup?

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My friend Jack has started seeing his ex-girlfriend again. They were perfect for each other the first time, he says, and broke up because he spent too much time on the road for work. After a few years of seeing other people, a twist of fate has brought them together. Now they’re rekindling the sparks and enjoying the reunion.

Jack says Merri is better equipped to navigate the time he spends away, as her ceramics business has taken off and she travels herself on occasion to do workshops in nearby cities. They didn’t really have any other major problems and still have deep feelings for each other.

I have another friend, Kelly, a girl who never got over her player boyfriend. George treated her badly, but she still feels an insane attraction towards him. When she saw his profile online, she threw caution to the wind and messaged him. Now he wants to meet up, and she wants to go for the hot sex. She hopes she can withstand the heartbreak, but says it would be worth it.

Should You Date Your Ex?

Why didn’t it work out in the first place?

People break up for a hundred different reasons. Does the reason you stopped seeing each other still apply today? Is it something you have forgiven or moved past?

Some things that bothered us once don’t seem as important later on. Maybe you didn’t like the attention your gorgeous girlfriend kept getting from other guys when you were 25. But now you’re 35 and not as testy, and see how it’s validating for her—and you—to turn so many heads. You’ve grown up and aren’t the jealous type anymore.

Maybe, like Jack and Merri, a little bit of work in the way seems like a stupid reason not to be with your soulmate.

But if you broke up because your girl cleaned out your bank account and sent revenge porn to your mother, think again before you call, even if your dick is hard.

Have you both changed?

When we’re not meeting people we click with, it can be easy to romanticize a past love affair and think it could work today.

But you’re both different people now who have grown separately. This can work in your favor, but it can mean that true connection is a fantasy, not reality.

Is it just sex?

I would probably tell Kelly to “go for it” and just hook up with George, except for the emotional risk she would be taking.

Sex with an ex where the departure was mature and amicable can be the least messy kind of hookup.

But if there is unfinished business, if emotions aren’t resolved, or an imbalance of power exists, it can be foolish to think things are magically going to work now—worse, one or both of you might be mistaking sexual attraction for the desire to get back together.

Take a hard honest look at the situation, and assess if it is just a booty call.

Is it a rebound, fear you won’t find someone else, or is it real?

If you’ve just gone through divorce, you might be vulnerable to delusions of past grandeur. Maybe you’re going through your Rolodex because you don’t seem to be making connections right now, and suddenly a woman from the past feels like the one who got away. Don’t go there.

If both of you made mistakes in the past and let a good thing get away, and you’re better equipped now to rectify those things, a past love affair can blossom into something beautiful. It all depends on the unique situation at hand.

Have you ever hooked up with an ex? Tell us how that went in the comments!

Tell us what you think!

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