don't forget airline points! Also don't forget credit card points. I'm not treating you to dinner, I got his gift card through my discover card and now I got to use it

You spend so much money that 3-5% back pays for luxuries?!

That's besides the point. This is in the context of spending money on people when they get all weird about it. Saying that I got these points that are expiring so we have to go to dinner at a moderately upscale restaurant turns the table on "I'm buying you dinner because I want to spend time with you, I don't want to cook, and I know dinner at this restaurant is half your whole food budget for the month." into them doing you the favor of not leaving points/money on the table.

Still though, $200 for (half) of dinner, on a card giving 5% Cashback is $4,000, and that doesn't have to be spent in one month.

I do this- I just tell my parents I have a lot of frequent flyer points (which I do), but then depending on the cost and availability of flights I book whatever is most convenient for me.

It's generous, but not cash in your face.