Should you break up?

I send a newsletter about breaking up every year around Valentine’s Day. Counter-intuitive, maybe, when the shops are filled with heart-shaped balloons, boxes of chocolates (still an all-time great gift IMHO), and pink EVERYTHING.

But.

The “should I end my relationship?” question is one of the most common I get. Ending a romantic relationship, whether it’s been a few months or a few decades, is a hard, hard decision. Feelings don’t fit neatly into a decision matrix. Obligation, guilt, responsibility…all these kinds of tough emotional weights can really obscure what’s right for you when it comes to whether or not you should break up.

And these don’t just apply to your romantic relationship! Family, friends, co-workers…sometimes we need to decide when to break up with those people, too!

So—how do you know when it’s time to end it?

Over the years, I’ve come up with a few questions that will help you decide. ⬇️⬇️⬇️

❤️ Try to zoom out. If you look at your relationship over its entire course, is it mostly good? Or mostly bad?

And are there good parts all the way through? Or are the last few months/years/decades mostly bad?

❤️ Are you putting up with behavior you’d be embarrassed or ashamed to tell someone else about?

When it comes to discussing relationship issues with someone, we often leave out the worst parts. Are you in a relationship you wouldn’t want a good friend to be in? If you had a friend in your situation, would you tell them to leave?

❤️ Do you WANT to leave?

Breaking up with someone (a girlfriend, a school friend you’ve outgrown, a selfish parent) doesn’t actually require marshaling arguments and coming up with a list of issues. Wanting to leave can be the entire reason you end the relationship. If you want to leave, and can do it responsibly (I’m not recommending abandoning your kids), that’s all the reason you need.

❤️ If you knew things weren’t ever going to change, would you stay?

If the answer is yes, then congratulations! You’re one of the very few people I’d tell NOT to break up.

❤️ Are both of your romantic partners named Jason?

This was the case with one woman I coached, who was deciding between two men. If so, then it’s definitely time to break up, it’s all just too confusing, and you’re hogging all the Jasons 🤣🤣🤣.


People tend to think breaking up is always the “bad” option. But by the time people call me asking “should I break up with this person?”….the answer is, nearly always, that the relationship is over. And breaking up feels bad in the moment, but it feels great in the long-term. Let’s make good decisions for our Future Selves.