Thing is though he's living his best life with his sugar mama.He’s an idiot for caving in. Clearly the gifted life style is worth it!
She’s gunna be even more insufferable now
Also they’ve literally not spent a moment alone the entire holiday and that’s not exactly promising for their relationship if they just got engaged!
Getting engaged keeps her happy and keeps the freebies flying.
And then if he does marry her and they do break up (unless she gets a pre-nup) then he gets half her stuff.
So either way he is winning when you think about it. As annoying as she is, she allows him to lead a freebie life and for some people thats all they really want.