How to write out a flirt scene?

[fanfictionaxis.livejournal.com]

In one of my stories, I have my main male character who was dumped by his girlfriend over a year and a month ago, trying to figure out how to flirt with this one girl. He's totally unsure of how to go about it without being an idiot. He has no knowledge of how to flirt and his older brother is a known flirt and womanizer, he doesn't want to ask him for advice as he probably would tell the girl he's interested in that he's interested in her.

Where would he go to get advice for his friends who would have helped him are dead - would a bar be a good idea for him to go and talk to the bartender or should he just come right out and tell her that he's interested in her as a girlfriend and see where it takes them?

And here's the thing, I never flirted before so I am totally new to this.