I don't know your situation, but here's what we did: Every so often, I plopped myself down in my son's room and we went over how much he'd paid on his student loan and car debts and what his balances were, and strategized about which he should concentrate on wiping out first, etc. And then when those were paid off, we talked about how much of an emergency fund it would be prudent for him to have, and we priced the sorts of furniture he wanted and figured out how much all that would cost. Now, my son is naturally frugal and has trouble spending money -- he got that from me, and it's a double-edged sword, because now that's he's far more financially stable than I am, it still took him several months to buy new jeans and shirts that he desperately needed, because he could not make himself let go of the money. He was walking around in rags for several months, repeatedly saying he knew he needed new clothes.

Some kind of middle ground is nice if you can manage it. How old is your daughter, is she single, and is she looking for a frugal guy? Asking for a friend who would like more grandchildren.