On a first date, do you feel awkward letting the other person pay? I really hate it, even when the guy insists, because it makes me feel guilty if I'm not interested in a second date. (Even if I am, I hate it, but I feel like in that case there's more of an opportunity to make it even.) Especially if the other person does not make more than I do. I know it's supposed to be gentlemanly and a kind gesture, but I find it automatically assumes gender roles I'm not interested in and puts me in the position of debt, which I don't like (especially if the dude expects me to put out).