My parents are hilariously anti-mustachian.
For 5 years they made $60K/year, with no housing costs (dad was a pastor, they lived in the church parsonage), this was "not enough" to save even an emergency fund. Somehow it was enough to go on vacation every year, eat out at least once a week, have a billion channels of satellite tv, get my mom a fancy DSLR camera, etc.
They moved a few years ago and were looking at 2 different rental homes. One had a rent of $2150/mo, the other was $1800. They went with the $2150 one, because otherwise, according to my mother, they would have had to put some of the furniture, and my dad's boat, in storage, and storage fees would put them way over versus paying more for the bigger place.
The term "temporarily embarrassed millionaires" is the most accurate description, really. They don't get that they're broke as shit, and I have no idea what they're going to do in 10-20 years when my dad isn't able to work anymore (they're in their late 50's; mom has never really worked), since they have zero retirement savings. In their minds, the way to wealth, or even being comfortable, isn't living cheap and saving the difference, it's a brilliant business idea that makes you millions, or winning the Publisher's Clearinghouse Sweepstakes (I have seen my mom fill out the forms for that and send them in). They had rental properties for a while, but they sucked at picking tenants, and then moved out of state without selling them or getting property managers, and they were all foreclosed on (I think 3 properties?). They had another business for a while that went under quickly. My mom's done several MLM's. Over and over, they come up with something that they think will make them rich, and it never works.
A lot of their spending is on appearances. The big house, 2 cars when only one person works (though modest cars that I believe are paid for), laptops for the 3 kids still living at home, a postpaid smartphone plan, my mom's clothes shopping habit, etc. My mom grew up very poor and I think she has a major hangup about not wanting to be associated with that. I remember as a kid, being told to brush my hair because I looked "like a kid from the projects," and my mother making nasty comments about the "welfare mom" she'd seen at the grocery store. They want to believe they are better than that kind of people, and put a lot of effort into covering up the giant shitpile that is their financial life. (Fun fact: my mom refers to my dad as a "financial genius.") They believe it all, too; they honestly think that they are not broke, not irresponsible, and their big break is coming any minute to rectify the injustices that life has given them.
Not surprisingly, my mother is also a chronic yo-yo dieter. It's the same mentality - instead of putting in the mundane work every day to change habits, she's always chasing the newest gimmick.
I don't talk money with them. I'll throw out little things - when my mom was telling me & Mr Tofu about how she got a "free" tablet for signing up for a 2-year contract with Verizon, we told her how we recently had switched to Ting and were only paying $30/month for 2 smartphones, and wouldn't pay anything for the first 3 months thanks to referral credits. I've asked her to contribute to the kids' 529's instead of buying them a ton of gifts (though she never will). Stuff like that. But the big picture is not something I want them to know about, because I don't ever want to be in a position where they're asking for money, and if they know that we have it, they'll try to guilt-trip it out of us.