How to ask a guy or tell a guy this? And should I tell him how I feel now or later?

This guy and I have a past. We were very good friends, talked every day hung out every other day and then something awkward between us happened and we stopped being friends. The awkward situation being that he said we were dating for a week, meanwhile I did not know we were dating. I wasn't seeing or messing around with anyone else, just him. We both started seeing other people, and now we are both single again. The relationship that I just had gotten out of was very emotionally draining. The guy I was with was verbally and emotionally abusing me through out our entire relationship. When the first guy and I were "together" He gave me a hat and sweatshirt that I never returned because my boyfriend at the time did not trust me going alone and he never was around to return his belongings. Christmas day this guy comes to pick his things up. We were talking for a little while, I ended up crying in his arms, he comforted me, kissed my cheek and told me that I am perfect the way I am I blurted out that because of my recent horrendous relationship that I was not going to date for awhile. After he left, we began to text, him saying "I know you still wanna be just friends but you didn't say we didn't have to be friends with benefits" and I responded "if you wanted to be more than friends I would not rule that out" he replied "Yes, just friends for the time being you know?" When we had our thing before, we hooked up plenty of times before he said we were dating. So now the first question is that I really want to hook up with him. We both have great chemistry sexually and personality wise. But, I am prone to getting attached and get more feelings for him. I at this point, already have slight feelings for him (not to the point where I want to date) but just to get back to how we were so very close. How should I go about asking him to hook up? Should I tell him how I feel/what I want later or keep it to myself?
How to ask a guy or tell a guy this? And should I tell him how I feel now or later?
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