'Selling my condo [...] to move in with my now ex gf': 20+ expensive mistakes from regretful people

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Ben Weiss • Writer and Editor
Aug 29, 2023 4:00 PM EDT

Everyone has made an unfortunate money-related decision at some point in their lives. For some folks, it could be as small as buying a ridiculously overpriced sandwich. For others, it could be as big as a messy divorce. People don't always love to admit when they've spent an exorbitant amount of money on something. It's much easier to live in denial and pretend like it was all worth it. 

 

However, these brave souls decided to own up to their expensive mistakes on the Internet. Their stories were compiled via this thread on r/AskReddit. Who knows? Maybe their anecdotes could save someone from spending a ton of cash on a wedding they'll never remember or a house they shouldn't buy. Admitting your expensive mistakes is also not only potentially paying it forward to someone else, but it's also a step forward in absolving yourself of the guilt and second thoughts you might have been holding onto for years.

 

Keep scrolling below for these answers. When you're finished, check out these hilariously out-of-touch comments made by rich people!

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  • 01
    Hand - TSAVES OF ONE "What is your most expensive mistake?" ONEEL FORED DOLLARS DSTYTES 100
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  • 02
    Human body - r/AskReddit - Posted by u/lugulaga 18 hours ago What is your most expensive mistake?
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  • 03
    Font - LittleAmiDrummer 20 hr. ago Not buying a house when I was in the 3rd grade ↑ 2.9k ↓ Reply Share
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  • 04
    Font - nmeofst8 17 hr. ago I moved in with the wrong people and lost 95% of my posessions. It's a long up story but basically they changed the locks while I was at work and I couldn't get to anything that proved I lived there and then they moved everything in a day with a moving service.. I can't even track them down because they were using false names and were apparently subletting instead of owning and they used false names when they rented the property. It was the most 1 been in my life. 598
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  • 05
    Rectangle - meowi-anne 20 hr. ago Not getting a handle on my mental health when I was younger. 363 Reply Share
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  • 06
    Font - Definitely NotADave 20 hr. ago Marriage ↑ 214 ↓ Reply Share
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    Font - TheReinsofFullnight 17 hr. ago I took a leave of absence from massage therapy school. They said if you DONT call within 3 months to say you're not coming back, you have to pay full tuition (10k and this was 2010). Well, guess who didn't call within three months.
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  • 08
    Font - Nasty_Ned 17 hr. ago I joke that my wife and I both have an expensive mistake that we own up to. My wife's mistake: Me circa 2013, "Hey, we have a spare room and I have an old gaming computer. People are doing this internet money thing and it could be fun." Wife, "Thats dumb." Me, "Yeah, I'll just drink a beer instead."
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  • 09
    Font - To be fair I probably would have sold when they were worth a few dollars and thought myself a genius. My mistake: Wife, "They are selling the two story down the street. We should buy it." Me, "That lady is an animal do- gooder. I'm sure those walls are soaked in I'd have to pull out all the drywall and maybe the subfloors." Wife, "Yeah, I guess so." The price? 120k. It sold most recently for just over 500k. That's yacht money. 142 Reply Share
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  • 10
    Font - Crazy_Stable1731. 20 hr. ago I don't know if this is still a thing, but back when I was a kid, there were these "talent agents" that would "hire you" because you had the looks/talent to be a star. This was just a scam for you to pay them a bunch of money (i think it ended up costing my parents around a grand) for acting classes that weren't real classes and other random fees. 124 ↓ Reply Share
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  • 11
    Font - flaming_poop_chute. 16 hr. ago I don't feel comfortable telling you the names of my kids 107 ↓ Reply Share
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  • 12
    Font - Vlaed 18 hr. ago Not taking better care of my teeth and drinking too much soda. They are in decent shape now but I've had to spend thousands getting them there. 101 Reply Share
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  • 13
    Font - Schumi_jr05 18 hr. ago Selling my condo 8 years ago to move in with my now ex gf. 62 Reply Share
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  • 14
    Font - Clemof Nazareth 19 hr. ago Kind of a first-world problem but was still expensive. Had our driveway resurfaced without prior HOA approval, cost $6,000. HOA fined us $1,000 and refused to approve the change even though three other houses on our street have the exact same resurfacing (apparently they filled out the request form first). HOA threatened to fine us an additional $100/day until we removed the resurfacing, which would have meant tearing up and replacing the entire driveway and sid
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  • 15
    Font - TrookvlltBlack - 15 hr. ago Chasing girls and relationships in my teens, twenties, and early thirties out of immature neediness. Burned a lot of bridges and hurt a lot of people. That and just being brutally immature to begin with.
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  • 16
    Font - Dad_Is_Mad 13 hr. ago I'm in Finance. I bought 100 shares of a little company because it me off that Blockbuster charged me $88 in late fees. With this I could watch them whenever I wanted for a flat fee each month and as a bonus, they actually mailed the DVD's to you in the mail...you didn't have to drive to town and go inside and rent them. I thought it was a cool idea. We didn't really have much money back then so when we budgeted poorly I sold them for a $2000 profit. Was kinda happy
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  • 17
    Font - 22Dogbone22- 20 hr. ago Wife #3
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  • 18
    Font - Mrepman81 17 hr. ago Wasting money on a huge wedding where barely anyone remembers anything. Should have saved it for a house.
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  • 19
    Font - carolizzy81 18 hr. ago I bought a florist shop. Two years later we had a recession and I lost it and all the money that went into it. Flowers are a luxury item and people don't buy flowers in recessions.
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  • 20
    Font - drdominant1 20 hr. ago Bought a VR Headset
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  • 21
    Hair - chobi83 17 hr. ago Co-signing for an ex gf's apartment.
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  • 22
    Font - servicefriends - 18 hr. ago Buying a used Land Rover. Nothing but major issues and thousands spent on repairs
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marriage askreddit relationships divorce entitled expensive reddit thread Reddit funny money toxic relationship entitled people
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