First, let me say “You’re awesome, run away with me!”
Erm, I mean, that’s pretty damn cool.
Hon, I saw the photothread before posting here. You’re a freakin’ hottie. Most ‘nerdy’ guys have been passed over for not being jocks, and when a (very) attractive woman shows an interest, there’s defintely a "who, ME?"moment followed by “Oh fuck, I’m so going to fuck this up. Damnit… how can I not ruin this?” moment.
Strong women can be intimidating, but bluntness can work for you too. If you don’t have any fear, you’d be surprised how useful being direct could be. “I like you, relax, just have fun with me.” Heck, if you lay your hand on his and/or kiss/snuggle up to him, I’m sure his nervousness will fade soon enough. And, yeah, guys (at least all the guys I know) assume that hot girls have boyfriends. Or, like a movie once put it…
“Girls like her are born with boyfriends.”
I’m not sure about the flirting bit though…
Looking into his eyes and/or hugging him and saying “Relax, it’s okay, I think you’re sexy.” would sure do it for me if I was nervous.