I'm a step father also, so I get it. Fortunately I don't have the hyperthetical problems like you have. Third option is take your stepson to get a rental car in his name. But pay for it, and get the full insurance package so nothing comes back to you. You can also tell him that it's not a freebie, and He needs to pay you back. That way if he doesn't pay you back, next time you can remind the wife He still owes you from the the last time.
I agree at 34 the hypothetical step son needs to grow up and become a man and take care of himself. But remember he still your wife's son, women tend to be more emotional then logical in these types of situations, just trying to keep the peace.
That's great advice...
I concur...
women & their children are not separable,
it's kind of a package deal...
I'd lay the law down & tell him it's a 1 time deal,
with the rental & ins., he needs to pay you back,
it's not a gift, it's a loan, a short term loan, like a month
& he needs to grow up become a man & fend for himself...
he's 34 for god's sake, time to cut the apron strings/umbilical cord
even for the mom
some things, you just don't ask too
nobody is driving my car/s trucks, especially not insured driver
even if my insurance would probably cover it
unless I'm also in it & they have to be insured to drive it
I'm not a rental agency, or their bank either
I worked hard for everything I got, they should do the same
I've gladly given people/relatives rides, or even cash (consider it gone)
that I didn't really want to but felt I should, for the families sake
or to keep the peace, but laid the law down too...
If they screwed me they'll never get my help again...
tough love even for kids, a 34 y/o man isn't a kid anymore
if it (car or truck in question) was a total beater,
or if he had insurance, it'd still be a hard maybe, probably NO