Ask Emily: When to Call It Quits


“Dear Emily,

I’ve been in and “on and off” relationship for three years now that is currently on its way to being “off” again. I feel we’re just stuck in a cycle of break ups and make ups, and I don’t think that it’s doing either of us any good. I love him, but I don’t know if it’s a good idea to How many times do you try to make a relationship work before calling it quits?

Thank you,



Dear Jane,

That’s a great question, and one that is pretty common for daters everywhere. You’re in a relationship that doesn’t seem to be working, so you break up to get a better perspective- but then the minute the loneliness of singledom and the realization of being without your partner kicks in, you suddenly question your decision. It is normal to seek the comfort and familiarity of a recent ex, but when it turns into a recurring practice of breakups and makeups, can the relationship ever really recover?

I have a theory: if you have done the breakup, makeup thing more than two times you probably should end the relationship. One breakup might be helpful to show you what needs to be worked on. But if you get back together with a promise to work on things and find that nothing has improved, how is another round going to help?

There is a breakup side effect that I like to call ‘relationship amnesia.’ This happens when we tend to glorify the person after we break up with them. We miss them. We think of all the good times and their best qualities and think, ‘Maybe I gave up too soon?’ This is a time when you should absolutely trust your decision. You broke up for a reason (or several reasons). You get back together and the same stuff starts to happen, and then you’re right back where you started. Once the hot makeup sex is over, all of the issues- the hurt, the resentment, the bad habits on both ends- are still there, crouched in the corner. Unless you’ve both made efforts to improve the relationship, history is bound to repeat itself.

Every relationship is different, and relationship advice is definitely not “One Size Fits All”, so it comes down to your gut. If you have given it your best effort, and the relationship is still not working, there is no shame in calling it a day. Make the decision that is best, not the easiest.



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