Ask Wendy

Should I Try to Reconcile with My Ex-Boyfriend?

Friday, July 6, 2018
Graffiti on garage wall "you're going to be fine"
Hey Wendy,

Should I reach back out to my ex-boyfriend to see if he's open to trying again?

My relationship ended last month, with a man whom I thought was "the one". I wasn't expecting the breakup, and needless to say, was heartbroken.

I mailed him a closure letter, and he actually mailed me one back. It was a very kind note, explaining that his breakup with me was not logical. He didn't feel like we connected in the way he hoped for, so had to listen to his heart.

Of course, I can't speak for him, but from my perspective, relationships aren't black/white, and we had chemistry. We "checked off" each other's boxes. He is highly sensitive, and more emotional than I am, but it didn't necessarily bother me. Except he could be high-maintenance at times. But I was willing to accept him because I loved him.

Anyway, he said to me a few times that he just wanted to be happy with me all the time. Which isn't really realistic, and I told him so.

Looking back at our relationship, there were a few moments where things didn't go perfectly, and we had miscommunications. I think it was those moments that led him to think things weren't going well. As well as the fact that I don't necessarily love everything that he loves, in terms of comedies, TV shows, etc., and he's told me he wished I did, so he can share some of his joys with me.

I think he wants a fairytale, hobbyist-type relationship, and it's not realistic, imo. Hobbies change, and there's no relationship that's always happy.

Is it a good idea for me to reach out to him, and see if he's open to seeing things from a different perspective and trying again? Or should I just let this one go?

Sabrina L – Dallas, TX

Hey Sabrina,

No! No, no, no, no, no, please, no.

There, now that we’ve got that initial primal scream of hell-to-the-no out of the way, I want to say thank you for asking my opinion. Circling back to see if you can go another round with this one is a bad idea—let this shishy go.

Because really, what chance do you have at happiness? You’re asking me if you think it’s a good idea to reconnect so that you can then watch him leave you in eight months when the reality isn’t matching up with his vision of perfection?

You said it yourself, he doesn’t have a strong grasp of the realities of partnering. This is one of the worst kinds of relationships to try and salvage.

How’s it going to feel when you’re back together, but you know there’s a high probability that he’s gonna bail the first second shit gets real? I mean what if he’s watching Santa Clarita Diet and you just can’t muster enough enthusiasm? Or he’s waiting for your laugh at the right times at Caveman? Sabrina, it’s just too hard to walk on eggshells while trying to enjoy whatever it is he enjoys so he will love you more.

I know dating isn’t always a blast—boy do I! But I’m going to ask you to get out there and do it anyways. There’s no such thing as “the one,” but if you’re determined, you can find the man who knows a good thing when he sees it and is willing to enjoy the fun times and weather the bad. Someone who has your back, even when circumstances are less than ideal.

Good luck out there.

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