The Worst Money that I’ve Ever Spent: A List

Everyone makes mistakes.

Sometimes, those mistakes are funny.

Sometimes, they are sad.

I thought it’d be fun to take a trip down memory lane for all my spending fails ever. Here’s a top five list, along with all the lessons that I learned. (#5 is my favorite.)

#1: Not asking one question at the doctor’s office.

The cost:

$249 at the dentist + $426 at the optometrist

What happened:

I was healthy. I just wanted a dental cleaning and new contact lenses.

I had dental and vision insurance. The receptionists even told me they accepted it.

What happened? I didn’t ask the one question that would’ve made all the difference:

“Is my insurance in-network?”


I still don’t understand why doctors don’t tell you this upfront. But at least I know now to ask.

The only upside was that I put this on my new AmEx Blue Cash Everyday Card. My consolation was a $200 cash back bonus.

Lessons learned:

  • The receptionist is not your friend.
  • If something isn’t clear, ASK. Be persistent. Don’t be afraid to be annoying. This is true in general, not just the doctor’s office.
  • Have an emergency fund. It’ll save you from dumb surprises like this. (I got this part right, thankfully.)

#2: Not actually running the Chicago Marathon.

The cost:

$205 to register + $475 on medical stuff + $275 to cancel

What happened:

This one’s a sad one.

Once upon a time (aka two years ago), I was a runner—a really serious runner. I ran the NYC Marathon and raised thousands of dollars for charity.

My dream was to tackle the World Marathon Majors. When I finished NYC, I signed up for Chicago right away. I felt like I was on top of the world.

Then one day, I felt something disconnect in my right knee. It was during a casual treadmill run. No pain at first—just a weird sensation. But something wasn’t moving in line with my foot…

I walked home, and weird clicking turned to fire. Ouch!!! I had to hop up the stairs when I got home.

It got worse. I limped everywhere. I couldn’t walk down the subway stairs, so I took Ubers to work. I saw a physical therapist for three months. I also saw a therapist because, um, I went from running 26.2 miles to not being able to walk.

It didn’t end there. Because I signed up with a charity, I still had to raise money for a race I couldn’t run. I signed a contract. It’s hard enough to raise money for a race. It’s near impossible if you’re not going to run.

I pulled my hair out for days. I didn’t know what to do. Mr. Boyfriend and my parents chipped in. In the end, I covered $275 out of pocket.

I didn’t think this could happen. I blindly assumed that I’d run the race. I blindly assumed I could raise money without a problem. I probably thought that I’d go the rest of my life injury-free. I was unprepared, which made this that much more painful.

(By the way, my knee is OK now.)

Lessons learned:

  • Check your ambition. Be gentle to yourself. You’re human just like everyone else. In retrospect, I should’ve given myself more time to rest after NYC.
  • Protect your downside. Prepare for the worst, because it can happen. I don’t think I’ll run for charity again unless I’m prepared to cover the entire requirement myself.

#3: That time I bought fake concert tickets.

The cost:

$65 for tickets + $40 on transportation

What happened:

Once upon another time, I was a concert-goer. (Boy, my early 20s were fun.)

The thing about NYC concerts: they sell out. Sometimes within minutes. Often, robots will resell tickets for 3x the price on StubHub. Ugh!

But I was ~~fearless~~. I went on Facebook and Craigslist. I connected with strangers. They sent me PDFs. In return, I sent them Venmo payments.

You know, it did occur to me that this was pretty dumb. But nothing happened to me, so I kept doing it. If anything, it worked pretty well. I saw STRFKR and LCD Soundsystem when they sold out. I got Ladyhawke tickets for below face value.

Then one time, Tiesto was in town. I didn’t know until the day before.

The show had sold out long ago. They were going for $120 on StubHub.

But on Craigslist, one guy was selling them for $65.

That was way cheaper than other resellers, even on Craigslist. That alone should’ve raised a red flag. But nope. I actually met this person to pick up physical tickets.

To be fair, they looked believable to the untrained eye:

Raymond Jones was probably a fake name

I was so ready. I drank coffee. I was going to rave all night. (But actually though, because the show went until 4AM.)

The show was deep in Brooklyn, and I was in Manhattan at the time. So my friend and I took an Uber. Guys, I took a $20 Uber there just to take another $20 Uber back. The bouncer took one look at our tickets and bounced us out of line!

Lessons learned:

  • If it’s too good to be true, it probably is. Don’t get scammed!
  • If nothing happened when you did something dumb, you still did something dumb. Just because something worked for you before doesn’t mean that it will going forward.
  • If you ever need to buy secondhand tickets, use PayPal. Buyer protection will save you. I paid cash, so I was out of luck.

#4: That time I went to Peter Luger with bad company.

The cost:

$79 for a lunch.

What happened:

To be clear, the food was GREAT.

I just went with the wrong people.

Some background—my college friend was leaving New York. Before he left, he wanted to go to Peter Luger, a Michelin-star steakhouse in Brooklyn.

We made a reservation. I was excited.

Then he decided to loop in two other guys.

Guy #1 was cool. I didn’t know him well.

Guy #2? I knew him in college. I never wanted to see him again.

Against my better judgment, I still went to lunch.

What happened? Guy #2 dominated the conversation. He bragged about his income. He bragged about his Midtown apartment, where he paid $2,000 for a room. He complained that this lunch was “standard” for him. He even told me that my job was a mistake and that I should get a job like his. (I didn’t ask.)

I don’t know what my friend sees in Guy #2. I feel sorry for him. He probably operates from a place of insecurity. But that doesn’t make him any less annoying.

Guy #2 went on like this for a while. It got to the point where I couldn’t enjoy lunch. I couldn’t even talk to my friend. He was busy nodding at #2’s nonsense.

Then something happened one hour into lunch.

Guy #2 switched to CHINESE. And my friend and #1 JOINED HIM.

Guys, I can’t speak Chinese. I couldn’t join in even if I wanted to. I literally did not understand what was being said.

It started because #2 wanted to privately complain about service. (FYI, switching to another language doesn’t make it less rude.) But it kept going.

In retrospect, I should’ve said something. Hello, can you see me??? But I was dumbfounded. Who does that?

I must’ve looked like this in real life:

For one hour, I just sat there, listening to what might as well have been gibberish. And I paid $79 for the privilege.

Lessons learned:

  • Trust your gut. I knew I wouldn’t enjoy #2’s company. I went to lunch anyway. Surprise surprise, lunch ended up being a dud.
  • If something isn’t right, say something. My friend didn’t know that I disliked Guy #2. And when I was there at the table, I should’ve asked everyone to speak English.
  • Don’t waste your time and money on people who don’t deserve it. No good will come out of it. I should’ve just organized something separate with my friend.

#5: The cheapest iPhone earbuds on Amazon.

The cost:

$1 to return the item.

What happened:

Oh no, this is too recent to be comfortable.

A few months ago, my beloved headphones broke. The horror! Music, audiobooks, and podcasts power me through my commute. I needed to replace my headphones ASAP.

But I was tired of spending money on headphones. They never lasted long. Sometimes, I’d lose them. Other times, they’d break on me.

Obviously, the solution was to buy the cheapest headphones on Amazon.

I’ll just let this picture of the packaging speak for itself:

Excuse me, why is there a “warming” on the box??? Why do I need to “pls connected” this??? This isn’t even a Bluetooth device!!!

I actually tried plugging this into my iPhone. Do you know the sound of radio static? That’s all I heard…

Needless to say, I went to a UPS store and returned this the next day.

Lessons learned:

  • Buy for quality, not price. You know that saying “you get what you pay for?” Yeah…

What was the worst money that you ever spent?

Have you ever spent money on something that seemed too good to be true?

Why does knee pain happen in your 20s?

[Featured photo: Nathan Dumlao on Unsplash]

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s