This one is personal. My girlfriend and I ran our first official Money Date last week. Awkward for the first 3 minutes, then it clicked. Found out we were both stressed about the same thing and didn't know it. That alone was worth it. This category is for wins. Big or small. Paid off a credit card? Win. Had a money conversation without it turning into a fight? Win. Finally looked at your bank account together? Win. Drop yours here when you have one.