Expert: Azure - 1/5/2007

Question
I'm 20 years old and I'm not good at knowing if a guy likes me or not. At all.  
My sister was married this summer and one of the groomsmen was one of my friends from high school. I was the maid of honor so we spent a lot of time together. In high school, we kind of dated for a while but it wasn't anything serious. Mostly, we were just good friends and I'm pretty sure he saw me a little sister for a long time. Perhaps even now. He's real close to my family. He's friends with my brother in law, sister, and Dad. At the wedding, he joked that he was going to be my date for the night because he didn't know many people so we danced some and talked a lot and at the end of the night, he offered to drive me home. I think I've fallen for him but it's complicated with him being friends with my family. Now that we're both in school, we're two hours apart too. I've visited him a couple times and we've gotten coffee but I don't want to push too hard and look crazy desperate. I just want to know how to let him know I like him and find out if there is any possibility of anything being there from him. How do I get him to see me as more than a little sister now that I want to be more than his gal pal?  

Answer
depends how assertive you care to be; you can wait for him to show interest (if he indeed has any), or you could invite him to dinner, a movie, a concert or some interesting school activity; then, if he accepts and you're feeling really assertive, you could tell him how you feel..nothing ventured, nothing gained..