We are in early fifties and have a group of friends I first met 26yrs ago. All dotted around country but generally meet up with families once a year. All professionals and all reasonably comfortable financially I would think.
One of the guys in particular is obsessed with money and over the years always talked about levels of mortgage & rates/utility bills/pension. He runs a family business, which he has built up since taking it over and recently merged it with a bigger company, yet always maintained that they still had a mortgage at same time as telling us he was putting his dividends into his pension pot, and then mentioning the high value of that pot! Maybe he did still have a mortgage, but why keep mentioning it?!
Now that the group are of an age where mortgages are being paid off (at least one if not both parties in each couple first bought when houses were v cheap) he has switched to pensions. At our last get together, he spent the whole of one lunch asking if we thought he would have enough pension (see above re large pot!) whilst at same time telling us all what a great deal the merger was.
My DH had to go talk to someone at other end of table, as the constant finance talk was winding him up. As DH said, he and his DW are almost certainly in a different financial league to rest of us following the merger (and we are v comfortable) but he is still obsessed with people's finances. His wife is lovely, they arent a bragging couple, I think he is just interested in money and is quite nosey.
Our DC came into an inheritence a couple of years ago. I have not told many people, but it is likely that our DC will be able to buy houses a lot earlier than the other DC of same age in the group, so we will no doubt get a few questions then!
I have no interest in any one else's finances, and therefore don't expect people to ask about mine, except to generally know if we can afford to do something.