maybe its just me but arent “pool tables” where ‘bums’ hang out? a little innappropriate place to go on a date, where the guys are basically on top of the girls.
and complimenting clothes: if it comes into the conversation, then do but its how you say it- eg: “my my, you look glamorous tonight!”-its a bit to dramatic and way to ‘mushy’. however, if you’d say “that top looks really nice on you.”-your just giving a small compliment, with out getting to personal.