Back when the men had to do all the asking, and all women were allowed to do was to wait?
Back when staying out too late with a man could get a woman labeled as a whore?
Back when if you got date-raped you didn’t dare complain about it, because it would never be prosecuted and you’d probably get labeled as a whore who falsely tried to ruin men’s lives?
I don’t.
No. Where men thought women were worth asking out, trying to win their hearts, instead of Hey come over to my place, we’ll watch videos and I can use you for sex.
Last time someone took me out was over 30 years ago.
Or as they used to say, “Want to come up and see my etchings?”
Hey, I ran into that one back in 1969. Except it wasn’t “watch videos”, it was “listen to music”.
You mean back when all it took to get a gal to go with you to Make Out Point was to buy her a root beer float and beat her old boyfriend in a game of “chicken” up on Dead Man’s Curve?
No, when women were thought to be someone worth proving yourself worthy of by your behavior, not car related.
It’s funny that dating in the '50s was brought up (ugh); he didn’t say it in those words but I think his impression is that the man should support the woman financially and since women he encounters have their own money to start with, the financial bar for men is way too high. Or something like that.
His father (my brother) has always been the sole earner in the family so maybe that’s why he thinks that’s normal and expected (you know, like it was in the 1950s 
).
I think it kind of depends on what they or your nephew means by “affluent”. Like are they looking for a successful professional man who can support buying a nice home and raising a family or are they looking for some trust fund recipient who can fly them around the world on never ending vacations?
For many young men, both lifestyles may be more or less “impossible expectations”.
I thought everything about dating in the 1950s was “car related”?
I strongly suspect that the percentage of men thinking that it’s important to behave well around their partners, whether while courting or when already married, hasn’t changed much. The details of the rules about what “behaving well” means have changed somewhat; but that’s not the same thing.