A girl confessing feelings for a guy

I've had a crush on a guy for a while. I'm not incredibly close with him, but he is a friend of my brothers for years and years. He is incredibly friendly, funny, and just an all around good person. I know back in the day he was interested in me (my brother told me), but I was involved with someone. However, a few months ago we became friends on facebook. I've always wondered about him, because he's just one of those guys that doesn't come around very often. However, the problem is, we don't know each other super well... it's not like we hang out on the weekends or anything.
I want to take a chance though, and let him know that I would love to get to know him better, but I really don't know how to do it, and I'm extremely nervous about it.
Would it be weird to message him about this? I really don't know what to do, but I feel like I will be full of regret if I at least don't try. Any advice (or encouragement) would be greatly appreciated :)

Go for it. You will never know unless you try. You only live once!

I think a simple "Hi, would you like to have lunch/dinner sometime?" would suffice. From there, it already depends what you want to talk about. Confessing that you like him would be nice, although, getting to know him should be a good start as well. Sometimes, there are things you'll learn about someone when both of you are alone.

Do you two live in the same area?

Maybe you should get to know him a little better before you jump in on this. Or maybe tell your brother to ask him about how he would feel about dating you now.

Why not start talking on Facebook?
I was in a similar situation. Ive known my bf since we were little because I'm friends with his sister, but never really close to him.. we lost in touch, but when we added each other on fb, we started talking and then we became really close and started going to dates etc and now we are together and very happy.

An invitation that doesn't sound obvious would be good here. You can say, "I want to try these new place out. Come with me and try it out too". Good luck.

What's the worst that can happen? He can de-friend you and stop talking to you? What's the best that can happen?

Yes, I think we are about a 10min drive from each other, if I'm not mistaken

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Originally Posted by kaley [Dear Guest/Member you have to reply to see the link.click here to register]

Yes, I think we are about a 10min drive from each other, if I'm not mistaken

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If you're talking on Facebook, why don't you mention something that seems like a good time coming up (i.e. a movie or concert), and hint that he might have fun joining you. Or if you work in a public venue, like a restaurant, pub, or store, think of something interesting about it that he might want to stop in for a visit when you're working.

Something that lets him know you're interested, without messaging him directly that you are (which is kind of weird since you don't really know him).