Dating is Complicated! Part 2

So do you even call this a date...
2 Examples Met both guys from my past
#1 - Met him from my undergrad college, while he was getting his masters We've been hanging out thru organizational events/rally's/EDs/etc He invited me to his open mic event Saw some people from other organizations there, but mostly I just know him. It was nice to go out have a coffee, and watch people perform live with songs you never heard before. Had to end it tho, because he was part of facilitating the event, so I left...

So it was just a hangout, see what's new and what's out there.

#2 - Met him in high school, we were in the same French class. He's a really sweet guy, I guess he said I started liking all his pictures on facebook, when all I've been doing is liking everyone's post/pictures on facebook. So he IMed me, asked for my number.
We started talking.
Then, I can't stop laughing, smiling, giggling... Feels like part of my life is happy again. May be my love life is blooming. Saw him last Sunday, 8/5/12. Had sushi for dinner. Talked, he played his guitar, which I really love. He's a well-rounded person. Very lovable, sweet,... He calls me and textes me all the time. I feel so special when talk to him. I only seen him once, yet he makes me feel there may be love didn't go away. But then, we talked about money and future... Even though he said, it's not all about money, he mentioned it. The income, making me feel like I'm not doing anything with life. Talking sucks sometimes.

Talking and dating is SUPER complicated.

What am I suppose to do on the second date with these guys. That was only the beginning...