McElroy said:
I know what kind of a friend I don't have. A girlfriend. And I'm not open to everyone - I have standards. Also I can't be that guy who goes in the middle of a group of women to ask one of them out and then just leave or awkwardly stare at the others. Beside money and status, women are the main reason I went to Medical School! Disappointed!!
I think I can see the problem here: when you walk up to a group- you address the group, not just one person in it- that's rude and (as you point out) awkward. What message does it send a girl when you walk straight up and ask her out without knowing anything about her yet, and ignoring all her friends? Not good.
You just need to walk up and be friendly to all of them. Show you can talk/joke with a few at a time, then keep doing that while you flirt with the one you like. If you can show you can get along with her friends, you'll have a much higher chance of her having interest in you too.