Me: 2008, him: 1993, big red flag? What should I watch out for?

edit: the date isn't happening anymore. he texted me asking if we could change the venue as he realized he can't really afford that restaurant at the moment (???, why was this realization so last minute) & i told him no worries i can pay for everything. he told me no way i could ever let a girl pay, it's not fair to the girl and also "emasculating" to him. hate that attitude. called it off and cut contact. thank u, next.

So I hit this guy up on Insta, and we’ve been chatting for the past few days, calling and video calling and all that. Tonight he’s taking me out to dinner; just a date, nothing more. I talk to my parents about everything, and they told me to observe his behavior but keep an open mind.