Should I (28M) ask my best friend (29F) out?

Throwaway account here, and yes the title seems straight forward. But I need a sounding board because it's a somewhat delicate matter.

So I (28M) have developed feelings for my best friend of 13 years (29F). We met in high school and had a lot in common, we both are artists (I did it as a hobby, but now she does it for a living) we have similar values, sense of humor and both make up the B in LGBTQ. She and our group of friends really got me through HS since my parents didn't/still don't fully accept this.

We drifted apart after high school going into college, as did most of our friend group at the time. I've been getting through med school. she graduated , got married and had a baby a little more than three years ago. After the birth of her child we didn't really talk all that much. I then hear form her about a year later and we went out for coffee to catch up. Apparently her husband cheated on her with one of his employees (yikes), told me about some more unfortunate things that went on the marriage. I felt really bad for her and decided to try and make myself more available to help where I could. I coordinated with some of our friends to help her with moving, I helped bring groceries to her, drive her around while she worked on getting a new car.

Around this time I realized I was catching feelings for her. I tried to ignore it because she didn't need that from me, it made me feel selfish in a way? Not sure how else to describe it. Its been a year now, she's settled in and has really come a long way since her world was flipped upside. My feelings haven't changed at all, I mean I love her to death as a friend as is but lately my feelings have intensified. Some of it is physical attraction, but a lot of it is her personality. She went through such a horrible situation and came out the other side of it a more confident and resilient person.

My buds are telling me that I should back off because she has a child and that I should just have a clean slate. Which is kind of a weird thing to say imo, it's not really a deal breaker for me. So reddit; do I dare shoot my shot? Or should I let this go?

TDLR; I want to ask out my semi recently divorced best friend of 13 years out but I'm getting mixed signals about it.

Posted Mar 6, 2026, 9:55 PM UTC

14
Loading comments…