She's 5'3, she's hardly even going to be noticed if she's someone's arm candy, she might be a hottie but in a room full of them she's not going to stand out.
If she is recognized and she's with someone older the automatic assumption is going to be that she's a sugar baby, you might be lucky enough to have a hottie on your arm but she's there because you're paying her, it's not because she's your girlfriend or she likes you.
$500 bucks an hour plus whatever dinner costs makes for an expensive date with at least a 99% chance that she's not even going to entertain the thought of letting let you fuck her, not to mention the awkwardness of trying to make conversation with someone you don't know and it's hardly likely you're going to have any common interests.