So, when is it required for the guy to buy the girl dinner or movie tickets, etc? I have no job (working on it) and am running low on funds and I want to take a girl out on a dinner date. Should I pay no matter what? Is this the case for every dinner date from here on out? Last date I went on with a different girl I bought her dinner and said something along the lines of "I wanted to take you out for dinner, so I'll pay" after she tried to get her money out. But when we went for hot chocolate, she paid. Things never progressed with her. So, OT, when does the guy pay and when should each person pay for themselves? before you call me a loser for not having a job, she understands my situation, and is even helping me find a job.