Ok... am I overanalyzing this situation?

I feel like I'm constantly on here posting stuff, but I'm trying to navigate these unfamiliar waters and it's nice to get opinions from people who are familiar with/have been in my situation or just an opinion from a different point of view. Thanks again for all the help! Here it goes:

Here's the issue: Talking to this guy, but I get mixed signals. Sometimes I think he wants to be more than just friends and sometimes I think he's ok with just being friends. I'm not sure how much of it is me over-analyzing every little thing he says (which is not uncommon for me, to over-analyze in general), or if it's actually me picking up on what he's really feeling.

I've been talking to this guy for 6 months... we met on a dating website. In the past 3 months, things have been getting more personal. Have been on a few dates, but I've been too scared to make the first move and he hasn't made a move yet, either. For the past 6 months, we've spoken 3/4 times a week (phone, email, text) and for the past three months, we've been talking pretty much every day... convos start somewhere at 11 am (intermittently, throughout the work day) and it usually continues again late evening and lasts for a few hours. I've told him that I really like him and he has said the same back. I've told him that I think he's kind of awesome, and he's said the same back. We've spoken about how it's going to be when the other person meets the family... blah blah blah. So it seems all good, right?

Here's what gets me, he says things to me like: "You're crazy for being single" which I interpret kind of funny (isn't that why he and I are talking in the first place? When I we talk about my impending coming out, he says: "Get used to being set up when you come out". Again... he and I are talking and things are going pretty well (so I thought), shouldn't I not be set up or not expect to be set up because, in theory, I'll potentially have a boyfriend (guy I'm talking to). And he talks about how he doesn't get a lot of love from other guys cuz of his style (which I am really into), so this comment kinda bugs me too, because he's getting attention from me, haha.

One thing he said which I'm not sure where to categorize: His best friend is a really hot woman... and I told him this. He showed me the convo with his friend where he told her and she was flattered. He essentially said to his best friend: Well, if he (me) and I don't work out, I'll set you two fools up.

The reason I'm posting and I'm confused is because we may be seeing each other in the next few days again, and I really want to make the first move... I really like this guy and I really want to kiss him. However, I don't want make the move if he just wants to be my buddy... so how does it look to y'all? Your opinions would be GREATLY appreciated!