I think it'd make more sense if he expressed with his face or whatever that he was recognizing his failure and trying a new pick-up line, because right now it just seems like he's rattling them all off without regard to the way the woman is responding.
Also maybe her reaction could escalate in stages. Like, the camera's on his face, with him looking to the right of the screen, he says his first line kind of normally, then cut to her looking a bit uncomfortable (e.g., looks to the side, rubs her neck). Then back to him, maybe include her in the shot, but have us only see the back of her. He looks a bit flustered, like he realizes his mistake, then he starts forcing the lines out a bit more rushed, and then she could start doing what she's doing now (e.g., making a face, "What?!").
Some of the dialogue could be developed a bit, though of course I don't presume to know what you're aiming for. Here I'm just pulling shit out of my ass for the ending:
"If I said you had a sexy body...could I have unprotected sex with it?"
She blinks at him.
"I just...I really want to have unprotected sex with you...please. *beat* Er, well if you want I guess we could use a condom -"
She slaps, freeze-frame with the text over the image, the bartender slaps, etc.
I think you could experiment some more with how her reaction could progress. I can imagine it going from discomfort => weirded out and/or pissed => blank disbelief, as in the little section above. But I don't know what would be funniest.
Okay sorry that was rambly, hope it was a little bit helpful!!