My parents still pay if they invite us out to dinner. We frequently decline because we don't feel comfortable with them paying but we also cannot drop $150 for six dinners on a regular basis. Technically we can "afford" it but we are also saving to college and don't enjoy restaurant meals with our kids. We almost never go out to eat as a family of 4 as it is. I try to suggest eating in but they are retired and don't really like to cook.
The in-laws have us over for dinner every week or two. We definitely come out ahead in the deal, even if we pay for the occasional meal out. It's just funny.
What makes it so interesting is they have this all money, but instead of going out and enjoying themselves with some frivolous things that might cost a few bucks, they're tight. Each year they've done one big thing like new truck, new roof, new siding, new kitchen. Next is new bathrooms. (Keep in mind these are on a 50+ year-old house that they've been in 35 years with few changes, or replacing a 20y-year-old truck.) So, tens of thousands of well spent money. But dinner out? Nope!
Gotta love them!
They have what they have because they're mustachian. Older, well cared for house. Decent cars that they keep forever. Careful saving over decades. Retired in their mid to late 50's. They have enough to be a little more relaxed now, but mustachian habits die hard. Beware, mustachians! Or, be inspired?