Rodrigo Velez Posted over 2 years ago Who pays on a first date? I always end up screwing it up when I try to pay she gets offended, if I don't try to pay then another gets offended, I always get if wrong, I don't even know what to do know. That happens to me all the time, paying, opening doors.. you get the idea, it seems as if women don't have a common ground on what to allow a man do or don't for them. Personally I like to pay when I'm one on one with a friend, girlfriend, first date, cousin, sister, etc. if there's more than one then I only for myself, and/or my gf (if present) and only if she likes it.