I (31f) don’t understand why my best friend “with benefits” (29m) doesn’t want a relationship with me

Girl, I've been in this exact situation and I am here to tell you that he is never, ever, ever going to date you. My FWB also bought me gifts. He took me out to dinner. He made me dinner and breakfast. We cuddled and watched stuff. We went to movies and bars and parties. Everyone thought we were dating. We weren't. Every time I brought up a relationship, it was always "I'm not ready" or some variation of it. I even posted online about it when it happened and got the same kind of advice you're getting and none of it even mattered because he was never going to date me.

At some point you have to accept that this is a road that goes nowhere. What is happening to you right now is the same thing that happens to "nice guys" who get friendzoned, except that instead of doing nice things for him you're giving him sex and companionship. No matter how much sex and companionship you provide, he will never want to date you. It is not going to magically happen like in the movies. He's just not that into you, probably because part of him is still really into his ex, and it would be genuinely sad if you were to give up on a new beginning because of this guy.

You should definitely talk to him about your feelings, but if he gives you an excuse again then write him off. Seriously, don't waste your 30s learning a lesson many of us learned in our 20s.

/r/relationships Thread