My turn to add to these lovely stories.
Mom: We have a new baby (first grandkid in a large family). So for baby's 1st MONTH birthday (don't get me started), she gets him 2 new outfits - price tags still on, $15/each. Knowing she likes buying gifts but sucks with money, I show her the local used baby clothes store - the only place I will shop for baby clothes (even for other people's kids). She loves it gets him another $10 worth of outfits that day (face-palm). For the 2nd month birthday (again, not me or wife doing/wanting this) we get a box full of outfits - probably 40-50 pieces, total spent was "only $40". Well... still too much, but at least she is understanding things. 3 month birthday - at this point, we have probably 75 outfits from all sources, 1/2 of which he has never worn, she gets him 3 brand new outfits, $15/each again. Told me it was too much time to shop at the used baby clothes store (which is closer to her house than big baby box store).
Baby outgrows the outfits before he can wear them, Mom gets pissed when we return the outfits for store credit (our normal thing when we get tagged gifts - then buy diapers).
This is the same lady who has her ENTIRE RETIREMENT savings of $3,500 (at age 59) in a savings account that gets 0.1% interest (she has a loan of $10k at 9.9% at the same bank). Can't show her where/how my $50k+ retirement is sitting (at age 26) because then she would ask for a loan since "I won't need the money for like 30 years".
Dad: he is just as great with money. Cashed in on his pension at 55 - as soon as he could, at a full 25% of its value, a whopping $247/month - less than the electric bill on their 4/3 house (in case all 3 kids decide to come home at once - which has happened a grand total of 0 times in the 10 years they've rented this house - yes renting a 4/3). He also quit his job 5 years ago to run his own business. At the time he had 15-20 clients and it made sense. In those 5 years, he's down to 3 customers and doesn't see the need to get a website to advertise his service based business, he still has an ad in the phonebook though, since that worked when he started his side job back in 1985. He has no idea why he can't get more clients.
*ranting/typing this up, actually makes me feel better about it. I mean, I'm laughing like an idiot right now at the stupidity I come from. Not sure when these laughs will turn to tears.