Especially if he is a jobless college student looking for a job, but is busy with schoolwork? And my parents don't give me money except for school supplies and textbooks?
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I think it's understood that the person asking for the date take the responsibility for the tab. However (big HOWEVER), I do think it is a courtesy for the person asked to at least make the offer to split or pay for his/her portion of the date. As I've gotten almost midway into my 30s and established in my lifestyle, this the norm. The women I've dated are capable in their own rights and often make the offer. It feels weird because I grew up in the era where the guy pays everything every time, and sometimes I'll pick up the whole tab anyway, but other times I go into the date without a notion of paying for her part. I've also come to the conclusion, now, that big dates are pointless until you've actually established a relationship. I mean... why? All you're doing is blowing money and time on something that may or may not be successful. It's not worth the headache. So each us ordering our own coffee or gelato or whatever sets an easy atmosphere for talking rather than expectation.
The question also leads us in the direction that the guy should always pay. I reject that notion as it puts the burden and expectation on us as men that we are to pay for things in the future without question. It starts us at a disadvantage of a one-way street of spending our resources without her even expressing reciprocity. And make no mistake, the expectations expand as you're together longer.
Guys or girls, if you ask someone out and can't afford to pick up the whole tab, then you're probably not in the position to have made the proposition in the first place. Be aware of what you can afford based on the chance that she'll not pay her own way. Additionally, you're dealing with another person. If the date is failing, be up front about it, thank the asker, offer to cover some of the cost, and say good night.
Getting back to the addition to the question: If you're on out-of-work college student, etc., then my advice is to hold your hormones in check and focus on something else. Maybe school or finding that job and stop falling back on your parents for support. Dating is just an unnecessary distraction.