Connect Confessionals

50 People Fess Up To Their Biggest Spending Regrets

Kelley MacDonald  |  April 10, 2020

From pleather GoGo boots to bartending school, 50 brave souls spill the beans on regrettable purchases — big, small, and everything in between.

Maybe it was a Facebook ad that made you pull out your wallet. Maybe your favorite style icon donned the newest fashion trend on the red carpet and you couldn’t pass on the chance to try it out yourself. Maybe you finally gave in to the fiftieth email promotion to upgrade a subscription. Whether we admit it or not, we’ve all had points of weakness when a trend or persistent marketing persuaded us to buy something that we either immediately or eventually regretted.

For me, that purchase was a package of 30 Boston Celtics tickets. The price tag was $3,000. It was a friend’s rave review of the seat location, as well as the thought of sharing the experience with friends and family. But I ended up using only 12 of the 30 tickets. Luckily, I was able to sell some tickets and gave others away as gifts; however, there were a few games when those seats sat empty.

This Public Airing of Regrettable Purchases Will Make You Feel Better About Your Own

If you think you’re the only one who makes regrettable purchases, think again. More than 50 people told us the funny, weird, sometimes cringe-worthy purchase they’d take back in an instant if they could. Here’s a rundown of their regrets:

  1. I spent $45 on one of those five-foot outdoor inflatable Santas. I set it up the first year I got it, and then came to my senses, and well…never again! -Charlotte, healthcare administrator
  2. White, pleather GoGo boots that zipped up the back. I had to have them. I was 12. -Patricia, teacher
  3. I once bought a battery-operated weed wacker…total waste! It could barely trim freshly mowed grass. -Anna, teacher
  4. Not one, not two, but THREE faux New England Patriots snuggies — from CVS. What’s worse is I can’t let them go. They will lurk and haunt me for decades to come. -Cindy, author, speaker & comic storyteller
  5. Even after multiple friends and family told us not to buy the wipe warmer for our baby, we bought it. Within five minutes of plugging it in, it set off the fire alarm. We never even tried using it again. -Molly, golf professional 
  6. I thought I was being proactive by adding things to my Amazon wish list but I should have double-checked before I added them to my cart and purchased. When I got my new shovel, rake, and wheelbarrow, I realized I added the child version of all three. -Jackie, AM coordinator
  7. We bought one of those machines that make soda water. But for whatever reason, maybe something happened to the bottles that came with it, we don’t use it anymore. We buy cans of Spindrift lemon-flavored soda water or we buy Pellegrino instead. But that soda water machine continues to sit on our shelf; what an eyesore, waste of money and space! -Nancy, teacher
  8. Bitcoin. -Spencer, commerce partnerships manager 
  9. For a trip around the world, I thought I had to have a “backpackers backpack” (even though I had never traveled with one prior to this trip) and bought the Osprey Farpoint 55 for it’s “clamshell opening” and matching day-pack. I’m pretty sure I started loathing the damn thing (day-pack included) after about a week, yet felt obligated to use it for the entirety of my 15-month-trip. I finally broke down and traded bags with my mom when she met up with me towards the end of my trip. Never again, Osprey! -Liz, creative partnerships producer
  10. I purchased a pair of orange shoes. Never wore them, hated them. -Bette, legal secretary
  11. I bought brand new skis, boots, poles, goggles and a travel bag for a ski trip to California. I used them three times while on the trip and then never again. -Ariana, engineer
  12. Trying to save money, I bought an inexpensive dresser from an online site. Sleek look, but within weeks it sagged in the middle and leaned precariously forward. When I compare it to a dresser I bought at a yard sale for $15 and must be at least 25 years old, but is well built and still sturdy, this is definitely one purchase I regret. -Lynn, teacher
  13. Four years ago I made the mistake of online purchasing the most horrible little orange futon daybed-lounger to use as my apartment couch. I swear I checked the measurements and read the reviews and it looked VERY mod and chic but when it arrived, well, it was like a mini mod and chic couch for kids. I got it at a discount (though it still wasn’t cheap) and couldn’t return it, so I used it for years. Sad. -Jessica, graphic designer
  14. Prepaid community coach bus tickets to NJ for my niece’s birthday. They changed the schedule without updating it online and the ticket agent told me to refer to the website for the schedule. -Steph, shopkeeper
  15. Many years ago, when I was too young to know better (26), I let the contractor building our house choose the stove for the kitchen. It was an expensive, state-of-the-art stove with bells and whistles like a grill and griddle. It was a monster to keep clean. Too much money that I didn’t have, and too many hours (that I didn’t have to spare) cleaning it. -Deb, teacher
  16. I bought an Adobe membership (like $50 a month). My new job requires me to use different software, and I forgot to cancel [Adobe] and paid that for like two years. – J., video producer
  17. I regret buying hipster-style glasses. I’m not a hipster and my Bostonian family and friends made fun of me. I was trying to change things up — never again. I lost them and don’t regret it. -Alex, producer 
  18. I bought a pair of Nike Roshe One’s in what I thought was my size — they’re about half a size too small. I couldn’t refund them, and out of principle of not being wasteful, I still wear them… I should probably see if they spark joy. -Kathleen, HR operations
  19. One time I went shopping for jeans. Tried on this blue pair and loved them. So I grabbed a black pair right next to the blue pairs and bought them without trying them on, assuming they were the same. The black ones had buttons instead of zippers. I hate buttoning my pants. – Julia, producer
  20. I think my biggest regret was a $700 payment to bartending school. I went for a few weeks, and then got a corporate job and never did anything with that little paper certificate. I do know how to make a mean margarita though. – Melissa, accountant 
  21. In my early twenties, I won a raffle for laser hair removal services. At the end of my last free session, the receptionist convinced me to purchase an expensive package to do my legs. She had to work hard to persuade me but I eventually caved and handed her my credit card. I immediately regretted it (I didn’t have the money to spend on something that frivolous) and only returned a couple of times before giving up and cutting my losses. I was not impressed with the outcome (I saw little of the hair reduction promised) and still have to shave regularly. -Stephanie, project coordinator
  22. My private New England college education. I wish I’d considered a state university and thought more about how college loan debt was going to affect me. -Mary, social studies teacher
  23. The charcoal toothpaste, Carbon Coco, that I bought after seeing the ad on Facebook hundreds of times. It was way too messy to make it worth the effort and was gross. -Caroline, lawyer
  24. I regret buying a French butter dish. I convinced myself it would make butter more delicious and spreadable but it just lurks empty on my counter. I’ve tried giving it away but no one else wants it. I’m sticking to my tub of Land O’Lakes. -Beth, teacher
  25. I completely regret the rug I bought for under my dining room table. We never use the dining room except for holidays, but the playroom is next to it and the rug is just the worst colors. I love my dining set and wall color but I think the rug ruins the whole room. And I don’t want to buy a new rug since we never use the room. I wish I didn’t rush and purchase it in the first place! -Courtney, director of marketing technology and wWeb
  26. I made an impulsive purchase online buying ridiculous shiny silver platform boots in the wrong size and the cost to return them is almost the same cost of the boots. -Jen, higher education administrator
  27. I regret buying a manual knife sharpener because my son-in-law gave me a much nicer and more expensive electric sharpener. -Margaret, retired
  28. I regret buying a Dr. Brown’s Bottle Warmer to warm baby bottles. I was desperate to get my daughter to take a bottle and was willing to try anything! But it didn’t help. And was a pain to go through the process of using. -Ashley, teacher
  29. In 1972 after a summer in Aspen I bought an uninspected 1963 VW Van for $300 and headed to my cousin’s home in Vermont. I chugged over the Rockies and drove all night. The next day bopping along I-80, the engine blew and I was towed to Des Moines, Iowa, where the garage mechanic gave me $50 for the van. I hitch-hiked the rest of the way to Vermont. Looking back I should have taken a Greyhound from Colorado, more reliable but a lot less fun. D., writer
  30. Having just sold our 1800 square foot home of 13 years, and having to physically touch everything I own, I was utterly amazed at the things I had. I held things up and thought, what the heck did I ever think I needed this for! Who needs three sets of measuring spoons? Michele, self-employed business manager
  31. Any monthly gym membership after the first week. Liz, restaurant manager
  32. “Doggles” or dog goggles. Worried about cataracts, I bought a pair for our pup but she dove on the ground head first trying to remove them. Should have known better than to try these on a very willful pup. $25 plus shipping — a colossal waste of money. Nancy, retired physical therapist
  33. I regret buying a shower head from Amazon. We had to put every piece together and then pieces were broken and it never fit correctly. We ended up recycling it. -Whitney, behavior consultant
  34. I regret buying a guitar. I intended to take lessons and never did. -Jo, forester 
  35. One item I definitely regret buying was a Free People dress that I just had to have. I wore it once. And of course, no one wanted to buy it off of me. Lesson learned!” -Kelly, actress 
  36. During one of my “self-improvement” phases, I impulsively purchased a “Learn How to Play the Guitar with Keith Urban” package complete with guitar and 6 follow along CDs. Honestly, WHO can resist Keith Urban?! The whole package is still in the attic waiting for my next attack of “self-improvement.” -Kristen, teacher
  37. I paid approximately $1,500 to a Wellness/diet coach for a year’s membership. It was supposed to include weekly weigh-ins, private counseling, meal planning/recipe help, and vitamins. I went twice. Ugh. -Cathy, receptionist
  38. A commercial ice maker that broke after a month. -J., restaurateur
  39. About 12 years ago we joined Direct Buy. They sold things at discounted prices and since we were purchasing a new home that we wanted to furnish we got sucked in. The prices were discounted but the moving fee to get the furniture from the warehouse to our home was totally ridiculous and made up the difference in the cost of the furniture. We had a three-year contract and we did use the company quite a bit but still thought we got suckered in. -Maureen, retired banker
  40. A hunting camp for my husband. I haven’t seen him in 8 years. -Liz, store owner
  41. A new car purchased a few months after my husband passed away. Never make large purchases/decisions when you’re not in a good place emotionally. -Lyn, rRetired administrative assistant
  42. I am usually fairly careful with money and spend some time considering my options and comparing prices on larger purchases. After purchasing and renovating an old Victorian home last year, I was in Lowes ordering some plumbing fixtures. I was wandering through the appliance area and saw a stackable washer and dryer that was listed on sale and marked “lowest price of the season.” The price was good, the dimensions were right and I decided on the spot to purchase the set. It’s always that motivating threat that the price will never be as good that suck you in. As it turned out, I didn’t need to install the w/d for 6 months after I had purchased them, which meant that they were totally in the way of every person working in the house. I then had to pay 2 moving men to move them from the basement up two flights of winding “old Victorian” stairs. The closet that had been retrofitted to use as a laundry area was too tight to slide them in already stacked. To make a very long story short….it took 4 adults, some engineering knowledge, a lot of bumps and bruises and a few swear words to finally get them in place. Oh no, that’s not the end of the story…I was so excited to finally use the washer….and then it sounded like a rocket ship about to take off through the roof. Put a call into my plumber. He asked if we had removed the shipping bolts. Ummm, no. Four adults then had to take the stacked machines apart again….you get the picture. I’m never allowed to call them for a favor again! –Erin, cafe owner, and retired laundress
  43. I regret buying fitness magazine subscriptions when I was in my twenties. I’d read the first one or two, and then they’d just pile up. -Tammy, partnerships dDirector
  44. A push lawn mower. -Lillian, technical recruiter
  45. I bought a Winsor Pilates DVD set in college. I think I used them for maybe a week, and then maybe five more times after that over the next decade. I spent more time thinking about how I didn’t use the DVDs than I did actually using them. -Christy, senior software engineer
  46. I signed up for a free one-week trial of Youtube TV so my roommate and I could watch some March Madness games from home instead of spending money at the bar. I forgot to cancel the subscription before the trial ran out and ended up paying more than I would have if I had just gone out. -Jenny, production accountant
  47. I got a set of plastic Adirondack chairs several years ago. I thought they’d hold up better in the weather compared to the wood version, and they came in really cute colors. They lasted about a year before cracking and getting pollen stains, so I ended up going back for a set of wooden ones. I should’ve gone with the wood ones from the beginning. -Sally, adjunct professor
  48. This is sort of controversial but…I really don’t like my cat and I travel a lot for work. I’ve had him for a couple of years, and I’m trying to find another home for him now. -Barb, sales director
  49. Quicken for tracking home finances. When I bought the program in 2017 there was no mobile option and it requires a new purchase after two years, so further investment, which feels unfair. Would have preferred the mobile option with a low yearly subscription over what I bought. – Caroline, lawyer
  50. I regret buying a large Milo tree for my property in Maui. The plantsmen I hired to plant the tree pruned it back to half its original size. Larger trees cost way more, so I would have done better with a smaller one. At least the Milo shows she is super happy now with vibrant new growth and huge leaves. -B., retired teacher

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