On Buying Drinks
The appropriate time to buy someone a drink is just before he or she has finished their current one. To do so any earlier would make it seem as if you’re trying to get him drunk, and once his drink is finished is, well, too late.
I am personally of the opinion that people may buy drinks for people they are interested in regardless of both parties’ gender, but ladies beware: more than one man has found this off-putting. Of course, if he finds me buying him a drink to be emasculating, than he probably isn’t worth a second drink in the first place.