Advise! Should I Let Him Go if He’s “Working on Himself”?

Dear Love Author,

I just turned 32 and my ex broke up with me a month ago. He’s almost 40, and if we talk about attachment styles, I’m more anxious and he’s more avoidant. (I say this because it was an issue in our relationship.) In the beginning of our relationship, (the first 4 months), things were great – we traveled, he courted me, I was treated like a princess. I even recall telling my friends the following, “wow, this guy is literally eating out of my hand. He’s in love.” I then followed my gut (long story), but let’s say I saw some text exchanges with his ex-girlfriend and saw he took her out a few times behind my back. He even spent a night “cuddling her.”

I forgave him, and we pressed on. I bet this was my mistake. The next 6 months were rocky. I was really struggling to trust him and every time we took one step forward, we took two steps back. He started going to therapy and some things changed – he started drinking less, his anger improved, he wasn’t kicking me out anymore after a fight, we weren’t triggering each other as much, etc.

Then there was a breaking point: he didn’t answer my calls one time when he was out, and he admitted to it. I lost it and our attachment styles/needs triggered each other AGAIN. I ended up yelling at him (same cycle I got stuck in after he made a mistake in the beginning), and calling him bad names. He then broke up with me, saying he couldn’t take the “bad name calling anymore” and the control.

Here’s my issue: I don’t know if it’s my ego or true love, but I find myself trying to win him back. I have met up with him to talk, we’ve kissed, we are planning to see each other again to talk and see if we can figure something out. Am I making a mistake? Am I trying to fit a circle peg in a square hole?

I love when you said the following: what marks a great relationship is a lack of anxiety. The ability to feel safe, heard, and understood. Is he talking about a future, is this building towards something, is this going somewhere? The first four months I felt very secure but in the latter, I did not. A lot of our issues were driven by my insecurity and lack of feeling safe. This is also my issue: if I just forgive him entirely (I think I have), can we try this again and succeed, but this time I’ll be less anxious?

I appreciate your help. 



Thanks for the kind words, Kristen. Sorry you find yourself in this predicament.

Alas, this is not a terribly complicated dilemma.

The only thing that’s complicated are your emotions surrounding it, which illustrate that love has an uncanny way of causing smart people to cease critical thinking.

The only thing that’s complicated are your emotions surrounding it, which illustrate that love has an uncanny way of causing smart people to cease critical thinking.

Let’s start off with an acknowledgement of the two positive things in your email:

    • a. You love him.


    b. He was good to you for four months.

But then again, pretty much every failed relationship consisted of two people who loved each other who had a good four months before reality set in.

That doesn’t mean those relationships should stay together. Neither should yours.

Read and cringe:

    • 1.

He cheated on you with his ex-girlfriend.

    • Multiple times. This, in and of itself, is largely unforgiveable. But you “forgave” him. Then…

2. You spent six rocky months together. There’s a big difference between a marriage having a rough six months and a one-year old relationship having a rough six months. A reasonable woman who placed a premium on her own personal happiness might have left. You stayed, only to discover…

3. He had a drinking problem. And anger management issues. And he kicked you out after arguments. And he ignored your calls.

4. Then he broke up with you, which is usually a solid indicator that he doesn’t value the relationship that much and doesn’t see himself with you long-term. Naturally…

5. You are trying to win him back. Thus, your letter to me.

I know I’m working off of limited information, Kristen, but regardless of placing blame (and he would fare poorly if blame were apportioned), it’s obvious you guys are a match made in hell.

Forget ego. Forget true love. Just pay attention to how very difficult things are.

That isn’t a sign that you are fated to be together and that you should work harder to preserve your love. That is a sign that you should cut him off entirely ASAP and find a man who is considerate, sensitive and secure. You may be an anxious person, but with a good man, most of your anxiety will melt away.

The only question is whether you would be open to dating a guy who makes you feel safe, as opposed to rejecting him because he’s not as exciting or unpredictable as your exes. I hope you decide to be in a relationship where you are cherished instead of dismissed

About the Author

A prolific love author who specializes in creating love stories often focused on the romantic connections between people which readers can identify with.