Is this whack?

In my opinion the “being a man” joke was overt used, and yes perhaps a bit pushy, but she is down for it for sure, My next move would be asking is she likes wine, and probably move towards setting up a date soon

Well, the texting here is a bit weird man. Not sure why you are consistently telling her that you're a man. I think she gets that part. She seems very down though. So, I would just move the interaction forward at this point

"Do you like wine?"