Question
 

Okay, I'm carefully venturing into this forum because I just need some advice! :)

There's a guy. He's my best friend's brother-in-law. I've been friends with her since 7th grade and friends with her husband since 11th. I'm also very close to the guy's mother. So, I'm already around a lot because I'm close to the family. Well, the B-i-L is single and I just love him to death. We aren't dating or anything, but I'd really love to. He just makes me feel different than other guys have before. Sometimes I think he's flirting and sometimes I don't know. I was in a relationship for so long that I really don't know how to do this whole dating thing. My questions are: Is there any tell-tale sign that he might be interested? What's the best way for me to approach this? I have to go about a little differently since I'm already close to his family, I think. We are going to be around one another, dating or not. So it can't get awkward. My friend and her husband are all for he and I getting together. So, as random and rambling as this might sound, any good advice?

I sorta like you in the respect that I haven't done "the dating thing" a lot since my last relationship. But I've found that since I've grown up a lot, I've become more forward. Maybe you could use a little forwardness to see what is there. I'm not talking jump his bones, or something drastic LOL! I'm talking about making the first move! Too often I think us ladies think that the guy is going to make the move...or has to...and thus we wait and wait. Not smart. Guy's are chickens often...especially when it comes to someone they're REALLY interested in and don't know how to approach them. He might be feeling the same way, but given the situation of your mutual friends, he thinks it may be acward. So I suggest simply asking him sometime if he'd like to acompany you to a movie...or to dinner...anything. If you feel more comfortable doing it as a double-date thing, get the friend and husband to go along - though that makes it less obvious that you're "interested".

Good Luck

If you "think" he likes you, he probably does. I mean, if his actions are giving you that impression, you're probably right. He could be sort of waiting for a cue from you, so I think you should suggest that you two hang out together at some point and see what he says. I know that's basically what Hootie said, but I had to second that one. :)

And I third it. I think many guys are absolutely flattered when a girl makes the first move. Just get it out there and that way you'll know. Some of the tell tale signs I noticed throughout the years are signs like if he does things regarding what you two talked about, asks questions about something u enjoy and he knows nothing about, if he take any chance just for an excuse to touch him you in some way (unless he is just the affectionate type of person with anyone), etc.

Well, I guess I just try not to get too optimistic! I kind of feel like he's sending me some interested signals, I just don't like to get my hopes up! His brother thinks I should ask him out. Sooo, I'm trying to get a pair of Titans tickets from my dad and asking him to go to that. It's not too much like a date, but it gives us an opportunity to go out by ourselves and see how it goes. Thanks for the advice :)