Why Does He Keep Pining for His Exes? How Can He Stop?

We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make YOUR CALL on the letter below by leaving your advice in the comments section. 

Why do I romanticize the past?

I am a 26 year old male with a bit of a chip on my shoulder. I’ve never had trouble meeting women or openly expressing interest without being overbearing (well mostly), however I’ve noticed that the last 3 years of my love life have revolved around exes. I not only let people back in my life that probably should’ve stayed gone but also have reached out in efforts to, maybe, mend a wrong I’ve done in the past. Regrets and/or second chances…

Any time I’ve tried online dating or asking people on dates I meet, it always seems forced and not genuine at all. Every time I’ve ventured back into past love affairs or flings, I’ve always gotten hurt as a result. Is there something wrong with me? Why can’t I break out of my comfort zone? Is there something in particular I’m doing wrong or need to improve. Help Please!

— Mike’s Shame

What should MS do differently?
Let him know in the comments below.



  1. Sounds like you like the drama. There’s something slightly forbidden or taboo about trying to rekindle things with an ex, which makes it more exciting. Yes, forcing yourself to meet new people may SEEM awkward and disingenuous at first, but it’s the necessary step of getting to deeper levels with people. Dealing with exes only SEEMS deeper because you have all this history, but it’s just more complicated with more guaranteed heartache, like you attest to. Force yourself to go on an ex diet and suffer through some small talk.

  2. Hi Mike,
    I’m certainly no expert, but it seems like you probably feel safe with these exes and dating is a scary idea for you. Since online dating isn’t working for you, I think your best bet might be to meet someone more organically. What I mean is that trying to FORCE a date/relationship is never a good idea. Maybe you’re not really in the right place to be dating, and you need to take some time. I would definitely avoid going on dates with any exes, but I would also take sometime away from the dating world. I think eventually, you’ll meet someone naturally that you’re interested in, and things will be much easier.

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