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Relationship Advice: Breaking Up Is Hard To Do

When a past relationship is holding you back…

Dear Adam,
Two years ago, my boyfriend of three years broke up with me. We have had very little contact since then, and when we occasionally bump into each other, I get all awkward and chatty while he keeps things super brief and moves on. I have never totally understood why he ended things – I thought we had something great, and all he said was that he did not feel strongly enough to keep investing in “us.” I tried to get him to share what it was about me that wasn’t working for him, but he just said the connection wasn’t deep enough. I have tried dating a little since then with no luck – and mostly I still think of him. I check him out on social media daily and fantasize about us getting back together and convincing him that I could be Mr. Right again. If there’s even a chance of our getting back together, isn’t it worth my trying to get his attention? I don’t want to miss a potential reopening door, but I also feel pretty stuck. Help! – Mitchell

Dear Mitchell,
One of the hardest challenges with any breakup is when things end in a fairly vague and anticlimactic way. The fact that he didn’t provide you with a laundry list of problems is understandably leaving you guessing. You want to fill in the blanks and come up with all the reasons why you didn’t make the grade – that way, you can feel some control and try to shape-shift into what he really wanted.

What would be less crazy making is this: consider that he is actually telling you the truth and that the relationship simply didn’t feel quite right for him, not because you have some huge deficiencies. In all the songs and movies, breakups are broken down into a good guy/bad guy scenario, which doesn’t serve any of us. Often a relationship ends not because someone did something egregiously wrong or because of constant spats, but because one or both people just don’t feel satisfied enough. It is so painful to accept when this happens, and it’s tempting to scramble and try to recover what was lost.

When we get really hung up on someone – which you certainly are – it’s often because we’ve put that person on a pedestal and assume that their approval would confirm that we are ‘good enough.’ So long as you keep pining for his validation, you will feel very small, which will only strengthen your need to get his attention. As you already know, this cycle is exhausting and pretty heartbreaking. From what you have shared, there is no evidence that he is questioning his decision, and your hopeful perusing of his Instagram account is just rubbing salt in your breakup wounds. A way forward is allowing yourself to grieve the loss of the relationship while resisting any idea that this breakup is some huge statement about you or your entire relationship future. If you keep feeding your fantasy that ‘getting him back’ would guarantee lifelong happiness, you’re destined to put your life on hold – and that will limit all the new adventures you could be savouring.

ADAM SEGAL, writer and therapist, works in private practice in downtown Toronto. Ask him your relationship or mental-health questions at

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