Q: I have been in a casual relationship for several months with a man who I consider to be a very close friend. We have occasionally spent the night together but have never had a conversation about it.
I want to tell him about my feelings for him, and let him know that if he doesn't feel the same or isn't interested in actually dating, then I can't continue to be his friend-with-benefits. The problem is, I always chicken out of bringing it up — it just seems too awkward, and I am afraid of facing potential rejection face-to-face.
Do you think it would be okay to write him a letter or email about this instead? That way he could process without being put on the spot, and be able to email me back, which might be easier for him, too, if he has to tell me he's not interested.
I tend to think this is just a really chicken move on my part, but I'm curious to hear your thoughts.
Letter vs. Face-to-Face
A: My inner oversimplifier wants to point out that if you had solid reasons to believe he felt the same way, then you wouldn't be so afraid to speak up.
The first gauge of sufficient maturity and trust to be in a relationship is the courage to take an emotional risk and withstand a painful rejection.
But you already know that chicken moves are for dance floors, not relationships.