How do you know when it’s time to break up with someone?

Illustration: Nadia Snopek

@AskPeaches: I’m a 26-y-o female who has been seeing someone for about 7 months now. My boyfriend and I have had a rocky start to our dating relationship, but it has not been improving. I’m not sure whether to stick it out or to end it. How do you know when it’s time to break up? Thanks.

@Megan: Thanks for sending me your question. We’ve all been there. It’s hard to referee the fight between your head and heart. I’m sure there’s more to your story than you’ve shared. But based solely on your message, it sounds like you do care about your boyfriend and the relationship. There’s no one-size-fits-all as far as relationships go on when to pull the plug — different people enter relationships for various reasons, have different value systems and their own breaking points.

That said, end the relationship if you feel you’ve exhausted everything to fix the issues with your boyfriend, and if it’s beginning to affect your mutual happiness and well-being. Take it from a person who has been there. Circling the wagon can become tiring, and it can become all too easy to enjoy the idea of being in a relationship, even if it is a dysfunctional one.

But, if there’s still a chance this could work, a place to start might be with a little introspection. I find writing things down and listing pros and cons work to put things into perspective. If your pros-list far exceeds the cons-list, then dissect the cons and see which ones can be remedied easily by your partner while paying special attention to any deal breakers. Also, answer these questions: Is there a personal reason why you have found it difficult to let go? What is it about this relationship or your partner that you still find valuable enough to still hang on in spite of the conflict? How aware are you of your boyfriend’s own frustrations towards you, or your part in the discord? How important is it for your partner to get beyond the mentioned issues? If your answers to these questions remain positive, then perhaps your relationship deserves another shot. Combine this with your cons-list and use them as a reference point for a free-spirited housekeeping discussion with your boyfriend.

Have your boyfriend agree to an open conversation. Lay down some ground rules so that the conversation is fair, constructive, and each person gets a chance to speak and be heard without interruption. I know this will be harder to do in real-life, but it is important, as things can go off the rails with emotion and tempers flying. Share your grievances and speak transparently about your feelings with your partner, including your thoughts of calling it quits. Sometimes, that level of openness can make the difference. Although you may not see eye-to-eye on everything, determine point for point where you can compromise or resolve an issue all together. Should this not work, short of professional intervention, you may need some time apart to reassess if the desire to reconnect with cooler heads is greater than the impulse to end the relationship.

The @AskPeacheas column is prepared by committee but written from one person’s experience. Send emails to askpeaches [at] freshfruitinc [dot] com with “@AskPeaches” in the subject line. Be sure to give enough background, so the advice can be more specific and relevant.

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