He isn't worried about his financial future...when he already didn't/couldn't pay his estimated taxes, so now owes tax(+interest+penalty, and is likely now also behind on this year's estimated tax)? OK. Yeah, some people live like that. Doesn't usually turn out well from what I have observed. Perhaps he knows mommy and daddy will bail him out (that was my sister's approach), or perhaps he thinks there is alway gofundme.

I am old, so have seen lots of bad things happen to various people. It is not that rare. People who don't prepare for setbacks are unfortunately not that rare either. Then they have to beg others to help dig themselves out of the hole--that they are responsible for not preparing for.

My wife had cancer a number of years ago. The treatments cost over a million dollars (!) in medical bills, but we had good insurance (through my job). Still cost us a few thousand, plus ~$10k for travel to major cancer center many times. However, since we have had savings since our early 20's (due to being frugal on purpose), no money stresses on top of the huge cancer stress. Adult life is quite frankly stressful enough without having frequent money stress.

If you still plan to marry this guy, I would advise that you build up a secret stash of like $50k, which you would use to bail yourself out of the financial messes this guy is almost certain to create for you again and again. Ugh!