The first date is an awkward enough experience as it is. You know each other enough to warrant a date but not enough to make assumptions. You never know, the date might go amazingly and then right at the very end you fuck it all up by trying to be nice and paying the cheque. Suddenly it's anger, apologies and then date's over, nobody enjoyed their time.
1. Date Didn't Go So Well
To me, a woman paying in entirety is a red flag, as in they don't want to give any impression that they want to have another date. Now if the date went badly and someone offered to pay for my food I'd definitely let them because fuck it, free food.
2. When Money Is A Problem
Now I'm far from flush with cash. Any dates I've been on I've offered, maybe bought one or two drinks and then let it get to both of us paying for our own. Buying a drink for someone is just nice to do but shouldn't really be expected because dates are really fucking expensive. If there's not gonna be a follow up date then it's just someone being an asshole when they let them pay for everything.
3. Sending Signals
I know it's contradictory to the other point, I guess it depends on how it's said but if a woman wants to pay entirely, it can mean there's gonna be another date. You'll get the bill next time? I'd see it as a good way to assert yourself as independent so they don't think they've to be macho. You find out of there's another date on the way, you assert yourself and if ye go on another date the money should equal out. As long as he doesn't suggest a walk in the park or some cheap shit like that.
4. What If It's All A Test?
Should I let her pay? Does she want to pay or does she want to see if I'll actually leave her to pay for it all? To be honest I wouldn't put it past anyone to test their date. I give it a second when ordering drinks, to at least see that there's the intention of paying. I need them to be okay with me being poor and not being able to spend money all night.
5. Chivalry Doesn't Have To Be Dead
I understand if you don't want me to pay for dinner. To be honest I don't really want to do it but it's just traditional and I'm okay with not deviating from it. Men are given the idea that they need to act as a gentleman. For the most part anyway that flies quite well. It's not trying to say anything about gender roles, it's just you want to show you aren't there to waste some time. Refusing to split the bill, pulling out your chair or opening your car door is really just us trying to show that we're serious.
6. Man Problems
See being a man I don't see a problem in me paying but because it's how things have gone for so long I feel emasculated when people buy me things. It's still very much in my head to be a provider, even though I can't take care of myself. Still it makes you feel less independent and almost like a charity case, even though that's not the intention.
7. My Cop Out Conclusion
I'd say for everyone's benefit just split the bill or make it plainly obvious that they can get the next one. Men can't see subtlety. Also it's the handiest way for you both to have a bit of control. I'd say if you don't have any intention of seeing them again split the bill, that way there's no feeling of owing someone a dinner on either side.
Video: Should Women Pay On The First Date?