No. I interacted with him on two occasions during the PayPal days. They were pitching PayPal as a payment mechanism for a bunch of our verticals. Even back then he was weird, awkward, and cringe. I think there is video of him back then taking possession of a McLaren and you can see how cringe he was.
EDIT: Found it.. On rewatch, it doesn't really show how insufferable he was in person. It's funny to see how x.com gets recycled though.
I've dated that girl. Not gonna lie, "uhuh" is hot as fuck.