We don't travel or do "experiences," and my cooking is mediocre at best (but slowly improving--I only slice myself open every other time I pick up a knife), so eating out is our Thing. We very rarely go above $50/plate (and don't even hit that price point all that often), but we do require that it has to be something I can't make at home. We spent $300 on our anniversary dinner (2 appetizers, 2 steaks, 2 cocktails, 1 dessert [well 2, but they comped 1], and a glass of cognac). It was delicious, they treated us fantastically, and we're going to make it a tradition to go to the same place every anniversary as long as we're in Chicago. They custom-print menus that say "Happy #th anniversary Mrs. and Mr. Xyz!", so we're going to collect them every year (we've gone for year 1 and year 2 now). It's a gimmick, and I love it.
That said, it's once a year. It's a very small amount compared to the amount I'm saving annually, and it's something we both enjoy very much.