With a hot single girl
Drink at her pace, so that when you finish together you can get her a refill, to imply a natural rhythm between the two of you. Don’t drink to get drunk unless she’s doing it too, with you. Because, naturally, if she’s trying to get drunk with another guy, it’s probably best you move on.

With your best friend’s girlfriend/wife
Drink with enough zest to make her feel she’s a friend, but not so enthusiastically that it becomes too intimate.

With your female boss
Drink modestly, even if she insists you have more. But, drink unapologetically. Don’t drink to try to impress her. Nobody’s impressed by a drunken macarena, drunken karaoke, or a drunken coma.

With your female co-worker/employee/subordinate
Drink modestly, with some polite distance. She’ll be watching to pick up social cues from you about how to drink with co-workers.

If with a celebrity, order an exotic drink

If with a celebrity, order an exotic drink

With a celebrity/movie star
Assuming you want to maximise the amount of time you get to share with her in the public eye, nurse your drink for as long as you can. This is why you memorise at least three awesome, unusual cocktail recipes. When she’s done, offer to refill her glass with the cocktail. She’ll forever associate you with that awesome, unusual cocktail. That’s the icebreaker you needed; now you can make your move. See With a hot single girl.

With your sister and female cousins
Don’t be their dad because (surprise!) you’re not.

With your sisters’ female friends
Drink modestly, with some polite distance. You don’t want your sister thinking you’re making a move on her friend. Unless you are. In that case, see With a hot single girl.

With your mother and aunts
Drink modestly. All it takes is one lapse to be branded the family alcoholic for life.

With your grandmother
If you’re lucky enough to have a grandmother who wants to drink with you, hang loose and bottoms up. Since she’s been there, done that and has a limited shelf life, she knows the value of a good time. Especially since she’s one of the few females in your life who doesn’t actually expect anything from you except to live to the fullest.

With your daughter
Drink modestly, because she’s learning from you how to drink. Drinking with your daughter can be quite cool. Unless she’s underage. In which case it’s morally objectionable. But still cool.Unless she’s way underage. Yeah, that’s not cool.