Dating a man 20 years older

Thursday | January 15, 2026

Love Letters Dating

Dating a man 20 years older

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

Dear Meredith,

I’m in my early 40s and dating a man 20 years older than me. We’ve been together for two years, and from the start I was clear that I wanted a long-term, intentional relationship, which he said he wanted, too.

We share values and have fun together, but we don’t spend much time together, and he’s inconsistent about integrating our lives. When I raise this, he is open to these conversations and says he sees a future and is open to moving in together. He points out that anything I’ve asked him to do he has done, but he’s very set in his routine and comfortable with things as they are, leaving me responsible for driving any change.

He’s been supportive with my young son, helps with things around my house and financially, but he doesn’t bring me into his space as openly as I’d expect at this point. I’ve met a lot of his friends but I haven’t met much of his family. While I’m home with my son most nights, he spends his evenings decompressing over sports and cigars, leaving me on my own in the evenings.

I feel stuck. He’s stable and I care deeply for him, but I’m questioning whether I want a future where I have to take the lead on spending time together and carry much of the emotional labor.

– Feeling Stuck

It would be nice to date someone who wants to decompress and relax with you (cigars optional).

I can’t speak to this man’s hopes or dreams, but if he loves his life the way it is, he might want to keep it this way forever. That doesn’t work for you.

Instead of pointing out his inconsistent behavior and telling him how you feel pushed aside, ask him: “In your dream world, how would this grow?”

Don’t give him answers. Let him design the life he wants, out loud – with a timeline of his choosing. Then you can think about compromise, and whether it’s possible.

For the record, my guess is that things are great for him as is, and that you’re always going to feel like you have to push him out of his comfort zone.

It would be nice to have a partner who’s enthusiastic about spending time with you. Please know: doing all of the emotional work in a relationship can feel a lot lonelier than having no partner at all.

– Meredith

Readers? Will this get better? Is it a dealbreaker if someone doesn’t see you or include you very much? Is there a way for the LW to accept and enjoy the status quo?

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

Dating