<human>: Classic bad rom-com scenario. This guy and I have been friends for a couple of years—always been very close friends who can talk about everything anything (including our respective significant others). And even in the past when we were dating other people, we would be somewhat flirty in a friendship-appropriate way. At one time or another, we acknowledged we had thought about each other in a non-friendship kind of way. But that was the extent. We hadn't said if there were feelings/romantic inclinations etc.

We both ended relationships last semester (if it's relevant, we both ended them, so I'm less concerned about being a rebound or using him as one). We had both been single for a bit and had been hanging out more and then we started hooking up. We've been what I'd call FWB for a month and a half. A month ago we had a dtr and he told me he wanted to keep things casual. At first I was fine with that. But like in every bad rom-com...I realized that I want more. I care about him. And being FWB means I lose the closeness we had as friends. So either way I want to "go for it" or end the hooking up and be friends again.

Anyway, I've resigned myself to being pretty vulnerable and finding a way to tell him what I want, despite how scary that is for me. The last time we dtr'ed was a month ago, so I imagine that's still what he wants. But I'd rather get a bit hurt then continue on this way. But I'm pretty nervous and don't want to chicken out. I'm hoping for any advice about how to approach things. How can I bring it up honestly but not too awkwardly? I've never gone from a friendship to a relationship, only just straight dating before.

I think it's a possibility he would be open to it. It's not hopeless, I just am doubtful. Probably a self-esteem thing/mixed messages we've been sending to each other.

Even any prior experiences good/bad outcomes would be appreciated. Just to hear advice/experience/ways of coping if he says we should just be friends would be greatly appreciated.

Could you distill the essence of the text into 1-3 sentences?
<bot>: I want to ask for a relationship with my FWB but I am not sure how to bring it up/want general advice (/encouragement?).