Holy Eighteen Benjamins Batman!!!!
I think the most I've ever spent on a dinner was in the $140 range for myself, as a date night maybe $200. One time was accidentally sitting down in Iron Chef Morimoto's restaurant in Napa, CA without realizing it and ordering the omakase. In my book, entirely worth the $108, but I only do that very rarely (once, twice a year? and only for special occasions).
Other times it's always been this amazing sushi bar in SoCal I only go to with a friend when I'm in town. Again, omakase, $120 a person or so in the end. (Some of you may be seeing a pattern here)
I'm fairly new to mustaching, my mustachismo is not as strong as many of yours, but I try to avoid eating out as much as possible for someone who works in downtown San Francisco and has 5 delicious food trucks across the street every day...lol
My "really adult, bro" moments were:
1) Financing a brand new SUV at the age of 22 (face punches). Granted, it did double as a tent on camping / rock climbing trips, and took me to many places off the beaten path that would've been difficult otherwise...paid that sucker off in full last year, sold it a few weeks ago, and the 20k is now sitting in my Vanguard account doing something useful.
2) Financing a house at the age of 24. I was semi-mustachian and made sure to have roommates as regularly as I could, but in the end I would've been better off renting than taking my parents' heavy handed advice to "invest in a home". Luckily, I was able to sell the house without paying any closing costs (new job's relocation package was killer) early this year at the same price I bought it for. Live some, lose some, learn some I guess lol