Every week we ask everyone who hangs out around here to answer a tough question. This week:

What’s the worst thing you’ve paid more than $50 for?

Rules are simple: What do you regret blowing half a c-note on? We all spend money on things we regret, but when did you really mess up? Did you get into an eBay war and lose sight of just how important collectable glassware is? Did you buy a plane ticket to somewhere you didn’t even want to go? Did you go to grad school, like, at all?

Alex Russell

Every year I go to Vegas with a few friends. We go in March, both because Chicago is miserable in March and because March Madness in Vegas is always full of degenerates, but mostly your happier, saner degenerates. A regret story about Vegas is nothing new, but it’s hard to pin down a “bad beat” any easier than this one. We were early for a dinner reservation, because your life in Vegas revolves around when you’re supposed to be where for what, and there was a roulette table right outside the restaurant. Vegas wants you to play, of course, but they want you to play impulsively. The $100 bet on black because I was hungry and frustrated was straight out of an anti-gambling PSA, and even though I know in my heart that Vegas is smarter than me… it’s rarely that damn obvious.

Alex Marino

Remember netbooks? It was that awkward time between laptops getting smaller and the iPad’s debut. People swore that netbooks were going to be the next big thing. I bought it because I wanted something for taking notes on in graduate school. I only installed what was absolutely essential for school stuff to keep it running fast. Well, it wasn’t fast. It sucked. And now I have a $200 dinosaur collecting dust in my closet.

Mike Hannemann

When you go to Epcot, sometimes you will want a drink. When you want a drink at Epcot, you’ll notice each country the park is divided into has a beer from that country. When you figure this out, you will want to go on a beer crawl of every country. When you do this, you will drink nine beers with high alcohol content. When you complete the beer crawl you will go to the Japan portion of the park and buy a $75 backpack that is a Goomba from Super Mario. When you do this, your parents will think you need to go back to therapy.

Andrew Findlay

I bought a pair of Mephisto shoes for 150 dollars. I was in Europe with a group for my friend’s wedding, and after they went off on their honeymoon we went to Paris. I had a pair of old, ratty tennis shoes, and I was ironically worried about them causing foot pain from the miles and miles I would walk there. My solution was to go to a shoe store and buy those damned Mephistos, which are like the Cadillac of supportive shoes. Seriously, podiatrist-recommended. They felt great for the first day and a half, and then I started experiencing sharp pains in the balls of both feet. One day in particular, waiting in line to go up the Eiffel Tower, the standing for more than an hour really did a number on me. Once we got up there, I immediately sprinted to the nearest bench and sat down without informing my friends of what I was doing. Because there are a shit-ton of people at the Eiffel Tower and because I’m an idiot, I did not see them again until we all made it back to where we were sleeping. I spent the rest of the vacation limping around, complaining about my feet, and being generally annoying to my companions. To this day, the balls of my feet still cause me pain, ranging from slight to significant depending on the day. I’ve bought a lot of crap I regret, but these motherfuckers ruined my vacation and gave me a lasting injury, and I paid out 150 dollars for the privilege. Clear winner.

Brent Hopkins

Fifty dollars was much harder for me to figure out than I would care to admit. I am a fan of saving money and spending it on big purchases, so I rarely have things that I am just disappointed in. There was something recent that didn’t sit well with me, and that was a motel I stayed at when my sister came to visit. Now, this motel was 38 dollars per night and we stayed two nights, so it amounted to over 50 in total, but I would have rather roamed like a vagabond than stay there. There was nothing aesthetically pleasing about this place and the bathroom looked like it had seen the Korean War in its prime. This was supposed to be a relaxing vacation but we were both awake by 7 a.m. and out the door to spend as little time as possible there. I was around there a few weeks ago again and just looking at the facade of the motel made me feel dirty. Never again will I go that far by my purse strings again.