1.
The plane ticket to New York City. I had already been accepted to the school I wanted to go to there back in 1995-96, but it was up in the air as to whether or not I'd actually be able to go with the cost of living so high as compared to the midwest. But, I went for it, and I'm so glad I did - living there taught me autonomy, mental toughness, and an appreciation for so many cultures, people, art, and especially FOOD.
2.
Our dog. I bought our Jack Russell Terrier while my husband was serving overseas in 2004 because I needed a cuddle-buddy. At first, Steve blew his top when he found out how much I spent on a pure bred terrier, and I assured him that he'd love this dog if not after seeing the puppy pictures, then after he came home (and that's precisely what happened, too).
3.
Our brand new car. This just happened this past weekend. A new Kia Spectra (much better gas mileage and better emissions than our old beat up used car that we'd had for years and years), and we were able to negotiate the price down from $20,000 to $13,000.