My advise: Proceed with caution. Do not tell him right away because you don't know this guy well. He could be a nice discreet person or he could be a massive prick who is going to call you names or tell everyone around. Information is power and you'll be giving him a lot of power by disclosing right away your occupation. Go on a date, maybe a couple dates, get to know a bit, see how he feels about the sex industry in the middle of a casual conversation ("gee... my neighbour is an escort and I'm friends with her, she's nice girl bla bla"_) Dip your toe inside the water. Then after 2 or 3 dates AND IF you are still interested in the guy (maybe by them you don't want to date him anymore, who knows) and he's a nice and open minded person AND you see some relationship potential then "drop the bomb", but not before.