Lingering Credit Card Debt
I opened a credit card when I was in college. I'm pretty sure I didn't get a t-shirt for that deal - I was careful to compare interest rates and perks before signing up. Ultimately, I don't regret the part where this card is my longest running debt: I've thought of it as betting on my future better decisions. So far so good.
I've gone through a few periods of knocking down debt - and the current iteration is the strongest so far: I'll be clear of my student loans in 2018. This credit card company (generically speaking so this doesn't turn into a commercial, but I'll name-drop if asked) has consistently treated me well. They always called when I traveled out of state and used the card without giving them a heads-up (back when I didn't know to do that, for fraud watch). And they have a few debt reduction initiatives that I'm now taking advantage of.
My favorite consumable vice in college: Sakura Gelly Roll pens. My professors were not impressed by handwritten essays in the almost-translucent orange.