I've known my bosses daughter for 2 years but we've never talked outside of work or ever been more talkative than a quick hello. I recently noticed her brush up against me when she talked to me and it seemed different than she's ever acted towards me before. Then 2 days later she requests me as a friend on Facebook. I found out last week that her and her bf had broken up. It seems shes on the market. She even told me she's looking for something "new and exciting." I messaged her on FB telling her I'm glad she found me on there. We have been having light talk about music, etc. She doesn't outright flirt but it seems she's at the border of doing that.

I told her we should go to a concert or hang out sometime and gave her my number. She said she will save my number but didn't give me hers. She seems somewhat interested in going with me someday to a concert. 2 days later she texted me from her phone that my FB messages didn't come thru and asked what I said. Obviously she got my FB messages but was just trying to find a way to subtly give me her number. I have told her I've always thought her to be beautiful and awesome. She seems skeptical of me telling her she was awesome cuz I dont' really know her. I told her it's because the way she smiles, laughs, and has a good personality.

I'm requesting any opinions or ideas on how I should proceed. I don't want to go to slow and get friend zoned, nor go to fast and fuck it up and scare her away. She seems to not really be offended about sweet things I say to her, though. She seems interested but kind of judging if she really wants to do this. I'm kind of confused on how to proceed. It seems like there's not going to be much room for error nor room for being a pussy. I have to jump in on this fast and smoothly. I keep suggesting that we hang out sometime but I'm done with that. I've mentioned it three times and don't want to be any more pushy.

First, stop firing so many compliments at her. You're ruining the challenge!

Now, I'm curious as to how you're asking her to go to this concert and shit with you. If you're merely suggesting that you do it "at some point", that's not good enough. You need to be more direct about it. Something like "Hey, N*SYNC is playing at the mall this saturday! You should like, totally go with me. Pick you up at 6?" With that said, going to a concert for the first "date" isn't always the best thing to do. Typically, you'll want to pick something a little less intense if you don't know her very well. That way, if you fucking suck, she can escape. Women love having that little bit of security. Go get bread pudding together or something instead. Leave the concert for the second date.

Nothing wrong with a single compliment o_O
I usually throw at least two out pretty early on so she's less edgy. No, you don't want to smother her with them, but I don't see two as too much. The awesome one... may have been wrong. But mostly because it's a statement of character and was out of the blue. You want to tie it with something. Like when you were talking about music and she agreed with you on a band = you're awesome.

I agree you shouldn't be trying to "win" her approval, but two compliments are fine.

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RSDTyler