Most Helpful Guy
I mean there are a lot of unknowns here... how were these "dates"? Who asked who out? Do you two talk at all sober? If so is it flirty good convo?
Its the guy's responsibility to ask the girl out but the girl's responsibility to make her feelings known. That's the system I've always worked with. Not to say it won't work if you were to ask him to start dating but most guys see it as desperation and most guys dont want to seem psycho or clingy by talking about feelings before the girl does.
If you have feelings for him then I wouldn't just give up... so I would attack it head on and tell him your not looking for a friends with benefits deal with him anymore... let him respond to that... if he cares about you or likes you then he'll say that either is he0THIS IS NOT RELEVANT ANYMORE