I was talking to an HB9 and i was being "cocky funny." So i was joking with her and had built up enough attraction when i made a neg about something. I remember she got really put off by it when i didn't think much of the neg. She kind of froze up and her body language turned off. Here's how i handled it
me: wow are you always so serious? You should work in a library. You'd be the hottest librarian ever. Wait wait check this out. Put your hair up.
*she does*
me: yeah that's money right there.

This only worked because she really did look like a hot librarian by the way she was dressed, but in any other case i think i would have had a lot of trouble rescuing the situation. How else can you rescue a situation like this without seeming like a week or needy guy?