LOL @ Uber.
Anyways, this is how I would approach things. Yes he's probably being cheap, but the one who asks should pay. If he's persuing the relationship, then he should pay, until you get more comfortable with the relationship, then go 50/50 or the richer person pays more. Being in the friend zone confuses things, but whoever is pushing for the friendship to become something more should pay. Course it sounds like he's a player (that whole Slim Shady bit--I mean I like his music, but I don't want to be him. Haha).
As for your friend, she has your best interests in mind, but is going about this the wrong way, and will just embarass both of you, IMO. Tell your friend that you'll handle things, and drop the guy. That's my suggestion.