Flirting with someone shy

Gavia

Hi guys, tomorrow night I'm having one of my friends over for dinner and I've liked him for a long time. He's super shy and quiet and outright flirting kinda freaks him out whether he likes the person or not. I was wondering if any of you guys have had experience with this kind of thing, and if so, could you give me a couple tips on how to flirt more subtly with someone shy? Thanks!