He and his ex vacation together with their kids

Tuesday | January 20, 2026

Love Letters Breakups 🖤

He and his ex vacation together with their kids

Tell me about friendships, breakups, dating, or awkwardness situations. Send an anonymous question through the form – or email [email protected].

A man recently broke off our two-and-a-half-year relationship (I am a woman, 50). I’m devastated.

To be fair, we’ve gone through ups and downs for the entire thing. He’s only recently divorced (with young kids), and I have been for 20-plus years and mostly single.

The whole relationship started on a bad note. He wasn’t ready for anything healthy at all, but pushed the relationship. I even broke up with him at one point because I recognized that he wasn’t for me. But he clawed back.

We tried again; it failed again. He has kids, and he and his ex co-parent like they are still married, going on vacation together with the kids, etc.

After we met for the last time, I asked him not to contact me again for my own healing. Yet he did days later saying, “I hope what you said isn’t permanent.”

Thoughts?

– Contact

This breakup is happening, so you should be clear about your needs all over again.

Sorry you have to repeat yourself.

Here’s a first draft of what I’d write back, if I were you.

“If this breakup is real and our romantic relationship is over, I’m 100 percent serious about needing space, with no contact from you. This loss is devastating for me, and I need to get over it. I can’t tell you whether this boundary will last forever, but please think of it as permanent. I’m not interested in friendship. I don’t need you to check in with me. I need to focus on moving on and starting new chapters. Please respect my wishes.”

Hopefully the next time he’s missing you and grieving the relationship, he’ll stop himself from reaching out, and will find a friend instead.

If he tries to change his mind about the breakup, remember that parting ways does sound like the best decision. You don’t like the way this man raises his kids with his ex (a dealbreaker, for sure). Some people enjoy dating people who can happily share kids with a former partner, but it didn’t work for you – and you didn’t trust his choices, in general.

Be clear with him, then let it all go. It is devastating, but you’re making room for something less turbulent.

– Meredith

Readers? Is it really over? Is this a pause before they get back together? How would you respond to the ex’s question?

Relationships can be confusing. What’s on your mind about your own connections? Send an anonymous question through the form – or email [email protected].

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