How would you write this?

[Solaris]

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.

Solaris

[Melrick]

I'm assuming the bartender isn't the person he's interested in? If not then, unless the bartender is a friend, I doubt he/she would be all that interested in offering flirting advice. If the internet is available in your story then he might go and surf the web for flirting advice, but he might tend to get rather overwhelmed by all the largely conflicting advice available. He might just decide to go it alone and jump in with both feet, as it were. And if he's bad at flirting then he might come on too strong at first, especially if he feels he needs to compete with his brother, even if the competition is within his own mind only. So he might get told off by her, causing him to slink away and contemplate giving up. But if he's determined, he might come back another time and just be honest that he likes her, etc etc.

That's my idea, anyway.

[Cuzosu]

And, honestly, him (and you) being new to flirting, some fumbling is expected. A total newbie NEVER gets it all right on the first try. If he's doing well, he'll probably get too encouraged and take it too far. Stuff like that.