I wonder if it might help to try honesty.

You could say, “I need to disclose that when I learned of the age difference, I got worried. I didn’t know how to handle that. But I trust that you know yourself, and I’m thrilled when you’re happy. I just wanted to make that clear because I might ask a few extra questions sometimes. My motives are good, I swear. It’s your happiness I care about.”

That’s a bit of a soupy word mess, but you get my point. It’s the tone that matters.

Please don’t tell her you want “what’s best for her.” That makes you sound like a parent who knows her pre-determined path. What’s best for her might be dating a guy in his mid-40s until she gets sick of listening to Pearl Jam in the car and decides to be single again.

You say she talks about her relationship problems. That’s a good time to ask very open-ended questions, even about the happy stuff. “What have you been enjoying about the relationship?” “What has changed since you’ve started dating?” Try those to kick things off.

Most of the time, just listen. That’s what friends do. Hopefully she’s asking you about your life, too. If not, that might be part of the problem here.

– Meredith

Readers? How have you let go of your own issues when dealing with a friend’s choices with a significant other? Is this on the friend for talking about relationship problems and expecting anything else? Is this about values or judgement?

What’s on your mind about friendship, love, exes, dating, love, loss, crushes, marriage, etc.? Submit your letter by using the anonymous form, or email [email protected].