(Nick Galifianakis/for The Washington Post)
Advice columnist

Adapted from
an online discussion.

Dear Carolyn: I am a 46-year-old divorced woman, no children, in a new relationship with a 53-year-old divorced man. My marriage ended about 10 years ago because we just weren't a good fit, and my boyfriend's ended much more recently and for a more heartbreaking reason. He and his wife lost a daughter to complications from an eating disorder before her 21st birthday, and their marriage fell apart as a casualty of their grief.

My boyfriend seems to have a healthy perspective on what happened and is sharing the details with me in gradual, responsible doses, but I often worry that I'm saying the wrong thing or not saying enough. I also find I'm self-conscious about asking for certain things in the relationship because he has been through so much.

Do you have any suggestions about not letting the specter of this tragedy harm a promising new relationship?

— California

California: This situation is indeed devastating. I think you’re good to be so thoughtful, and it’s a promising sign both that he’s sharing gradually and that you’ve chosen to be respectful of his timetable.

I am a little concerned that you might be erring too much on the side of holding back. It’s normal to be self-conscious — but so helpful if you can articulate that sometimes: “I find that I’m self-conscious about asking certain things because you have been through so much.” Don’t bring this up constantly — you don’t want to shift the responsibility onto him for your emotional caretaking — but do venture in at key points when you feel yourself holding back and wondering if he’d actually appreciate more openness. This allows him to understand what it means when you don’t respond to him right away, for example, or in a way he might not have expected.

Likewise, if you have the presence of mind in a moment when you’re not sure what to say, say that: “I worry that I’ll say the wrong thing. Is there something people have said or done for you that helps?”

Again, not every time, but at moments when it feels right. That gives both of you a voice in the pace of your emotional discovery.

Otherwise, keep up the patience, listening and compassion.

Dear Carolyn: I tried to be friends with an ex-boyfriend and just couldn't do it; the feelings were still there and I found it difficult to watch him move on with his life without me as a major part of it.

I made the mistake of telling him this, and now, though my feelings have faded, he continues to hold me at a weird, lordly arm's length, telling me — and others — that he's doing me a favor by giving me space. Is there a nice way to say, "Uh, actually I'm over you" that seems believable?

— Ex Friends

Ex Friends: “If I wasn’t before, then I am now. Thanks for the push.” Not that he’ll get it; you will, though, and that’s what matters. Congratulations on shedding this one.

Write to Carolyn Hax at tellme@washpost.com. Get her column delivered to your inbox each morning at wapo.st/haxpost.