Sure! I make... no guarantees that will go well, but I'm all for finding out! And hey, yes, show her the good bars pls! Also try and make her be social with people, it can only be great. Also given how old she is I imagine she's probably at least conversant in the pop culture of most eras, if he wants someone who's old enough to talk 80s. (It was 80s, right? I have no clue what I'm talking about, whoops.)

He is totally welcome to flirt, she might even flirt back a little, who knows. She also might give him incredulous looks, it sort of depends.