How do I start up a conversation and/or start flirting with one specific waitress?

Hi guys,
hopefully you can help me with one big problem of mine. I've been wondering how spectacular would it be if I succeeded in getting any attention form this one waitress I saw in a jazz bar week or two earlier when I went out. Firstly, I should describe myself a little bit.. I am a little bit more shy than I would want to admit, and can get very nervous if there's no luck in getting a girl's attention and/or number, but luckily I never show my nervousness. And even though I can be very chatty and easygoing if I know the person I'm with, it's very tough for me most of the times finding a real icebreaker.
Couple of my friends know that I'm just dying to get her number and most recently when I was with one of them after a long day of being out and doing stuff, we headed to the bar but it was to crowded because of a jazz jam concert the bar has sometimes. And seeing it was like that, we left but I kept thinking I'll never succeed with her. I was so disappointed like that I haven't been in a while. Most of the girls I've been with are set up's and lucky breaks that happened accidentally, so this shows I'm not a DAWG or a PLAYA like other guys from whom she most certainly was hit on.
I need some advice on how to even start a conversation with her and how to flirt with her..(i thought I could complement her long brown hair , or ask her where did she got her lip pierced, but still I'm not sure..)
I really, really like her.
So I ask you guys if there's any kind of way to try to get to her? Because my most brilliant move, the first night I saw her, was to ask her about the playlists which plays in the bar with chuckling and in quieter voice. I can't stop thinking about her at the end of the day, and I would be really appreciative if anyone can help me.
I read so many articles about how to pick up waitresses, but I don't wanna pick her up, I want to mesmerize her and hopefully get her number.
- thanks to anyone who can give me any advice!
And sorry if my grammar isn't correct :P
How do I start up a conversation and/or start flirting with one specific waitress?
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