How would you feel if your were on a date with a woman whose ex/previous date just paid for the dinner date you were on?
ultimately i'm more interested in how she handles it then what he did. i know an insecure dude when i see one. that shyt ain't gonna impact me at all. but if she's entertaining it or acting like she couldn't refuse, then my main concern is that she likes the back and forth games, and that's a red flag for me.
on the flip though, if she came back and said "this lame just tried to pay for dinner... free meal if you want it, but we can also tell him to fukk off", then i don't care how it plays out. cause i know she's prioritizing our situation, not his attention-grabbing antics.