My last boss, a highly paid VP, would frequently ask me about my car and if I was wanting to get a new one. It was a 10 year old Honda, ran great, good fuel economy, etc. I was fine with it. I'd always respond politely that I wasn't planning to anytime soon. I know this must have confused him, since he looked at my lifestyle, what I made, and probably couldn't understand why I wouldn't want a new car since he assumed I could afford it (and I could, technically). My car was fine. He had a BMW and a sports car that he almost never drove - wouldn't want to let anything happen to it!
So fast forward a couple years, I get married, and one of the first things he asks me when I get back from the honeymoon is..."so, is your husband going to buy you a new car now that you're married?". Ah, so many things wrong with that statement.
He also told me once that he thought that eating out and getting carryout every night for dinner "really isn't any more expensive than cooking".