9 ‘Oops’ Moments That I Ultimately Paid For (One Way or Another)

Last week I needed to venture into my attic to check on some rat traps, so I grabbed my flashlight to help me navigate my way through the rafters. As luck would have it, the flashlight wasn’t working; the last person who used it forgot to turn the darn thing off, so the batteries died.


Anyway, with no spare C-cells in the drawer and an unplanned trip to the store in the offing, I was determined to find the absentminded dunderhead responsible for wasting my hard-earned money and precious time.

I began my investigation by barging into my son’s room. Naturally, Matthew denied everything.

Undeterred, I then interrupted my daughter’s homework session. But Nina insisted she was innocent.

So I hollered at the only remaining suspect. “Hey, Honeybee!” I screamed. “Did you use the flashlight recently?”

“No!” she fired back. “But you were using it behind the entertainment center last week.”


Hey, our lives are full of “oops” moments. If we’re lucky, they only end up being minor inconveniences, rather than major financial disasters.

Here now, in no particular order, are 10 of the most memorable scatterbrained events that have affected my pocketbook. Thankfully, despite my family’s best efforts, I’ve managed to escape relatively unscathed — so far.

How does my list compare to yours?

1. The jousting junkets

Guilty party: Me.
Financial loss: $260
Space cadet summary: A couple of years ago I spent an entire day meticulously researching, planning and coordinating a last-minute Hawaiian vacation. Unfortunately, I inexplicably managed to double-book our island junket during a week where I had previously scheduled a weekend trip to Scottsdale, Arizona. The Scottsdale mini-vacation was put on hold, but I was never able to sell the four baseball tickets I had pre-purchased as part of that trip.

2. The 401k fail

Guilty party: Me.
Financial loss: $232 (plus 24 years of investment returns)
Space cadet summary: One of the biggest no-brainer decisions any new employee can make is to take advantage of their employer’s 401k match. After graduating from college many years ago, I had somehow failed to check a box signifying my desire to enroll in my new employer’s 401k program. Even worse, it took several months before I finally caught the error.

3. The submerged cell phone

Guilty party: Nina.
Financial loss: $0
Space cadet summary: As a kid, at breakfast time I used to read a cereal box or, more often, something called a newspaper (if you’re under 35, ask your parents). These days, kids would rather text their friends at the breakfast table — which at least partially explains how my daughter managed to drop her cell phone into a big bowl of milk and cereal a couple of years ago. Thankfully for her, the phone was insured.

4. The submerged cell phone (Part 2)

Guilty party: Matthew.
Financial loss: $25
Space cadet summary: Then there is my son, God love him. One day, on a whim, he decided to impress his friends by leaping into a swimming pool fully-clothed. By the time Matthew remembered his cell phone was in his pocket, gravity had sealed his fate. Again, insurance saved the day.

5. The feckless fan kit

Guilty party: Honeybee.
Financial loss: $47.99
Space cadet summary: We recently purchased a new cooktop hood and a supporting fan kit. To make a long story short, it turns out the fan kit wasn’t really needed. So the Honeybee returned it. Several weeks later we were informed that we wouldn’t be getting a refund because “we” (ahem, Honeybee) had opened the original packaging prior to returning it, thereby voiding the terms of the manufacturer’s return warranty.

6. The contemptible coupons

Guilty party: Me.
Financial loss: $60
Space cadet summary: Benihana is one of my favorite restaurants. Last year, as part of Benihana’s birthday club, the Honeybee and I received matching $30 gift certificates. When I tried to redeem them one particular evening, I was politely informed that, per the fine print, they were valid Monday through Thursday. Unfortunately, it was Saturday.

7. The mighty mailbox

Guilty party: Honeybee.
Financial loss: $0
Space cadet summary: Never mind my recent car accident, whenever I want to argue that the Honeybee is a worse driver than me, I like to remind her of the time she obliviously backed our 2001 Honda Odyssey into her friend’s mailbox. It was a classic battle: the immovable object versus an unstoppable force — and this time the immovable object won. I’m unwilling to pay $500 to repair relatively minor cosmetic damage, so our minivan still carries the battle scars.

8. The sidelined subscription

Guilty party: Matthew.
Financial loss: $50
Space cadet summary: One year for Christmas, my son asked us to buy him a 12-month Xbox Live subscription for his Xbox gaming system, so we did. Two days after Christmas guess whose Xbox broke? Uh huh. Soon after that, my son used his saved Christmas and birthday money to switch allegiance and buy the Xbox competitor, a PlayStation 3.

9. The forgotten phone

Guilty party: Nina.
Financial loss: $25
Space cadet summary: Remember that well-researched Hawaii vacation I was talking about earlier? Well, on our way there, during a brief layover in Phoenix, my daughter left her cell phone in a bathroom stall. I know. Happily, an honest person turned the phone in to the airport’s Lost and Found Office while we were flying over the Pacific. I still made Nina pay for the shipping bill though. As you can see, kids like to text their friends while going potty too. Chalk that up as yet another loss for newspapers.

Photo Credit: Terry Whalebone


  1. 1

    Jim says

    My biggest flub was the time I left my car keys on the top of my car. The keys were spotted by some kid who took the car on a joyride and totaled it.

    • 2

      Len Penzo says

      Wow. Sorry to hear that, Jim.

      Now I almost feel bad for even writing about my “problems.”

      I can’t see anybody topping that. Well … unless somebody else tells me they fell asleep while smoking and burned their house down, or something similar.

  2. 3


    Nice, Every single one of my children have drowned at least on e cell phone. The adventures range from driving dirtbikes down creeks to dropping them into a toilet (I assume unintentionally). My biggest fail was letting a chain hotel talk me into a prepaid Las Vegas Vacation (3 days for $300). As it turned out, my wife had no desire to go to Las Vegas and we ended up going to Mexico, Isla De Mujeres. The trip was Las Vegas deal was non-refundable so that was money flushed down the toilet. The Mexican Vacation was great and we now go there every other year!

    • 4

      Len Penzo says

      Hey, in the grand scheme of things $300 ain’t too bad, Jose — although I’m sure Jim considers that to be petty cash. My kids waste $300 in electricity every year by never turning off the lights or television after they leave a room. 😉

  3. 5


    I am normally not a fan of phone insurance but it does seem you get your money’s worth. If I ever get my kid a cell phone I definitely think insurance for the kid’s phone might be a better idea than I would have thought before I read this.

    • 6

      Len Penzo says

      I do not buy extended warranties for anything, Lance EXCEPT … for my kid’s cell phones. Actually, I also bought extended warranty insurance for my kids’ other expensive electronic toys when they were younger. Believe me, it is worth it. I think I made money on every extended warranty I ever bought.

  4. 7

    Jessie says

    I borrowed my grandmother’s lovely topaz and diamond ring for the first dinner with my new bf’s parents at an upscale restaurant. Not being used to wearing rings, I left it on the restroom sink after washing my hands. Though I realized my mistake as soon as I got back to the table, the ring was gone. I reported the loss to the hostess, but she wouldn’t even take my name in case someone turned it in: “Are you kidding?”

    • 8

      Allyn says

      I’m sorry about the ring, Jesse. I would have turned it in. . . or at least left a note on the bathroom mirror that said “I found a piece of jewelry on the sink. If it’s yours, call <my phone#). Identify it and I'll gladly return it to you." (Because I turned in a watch once and the hostess tried to keep it instead of giving it back to the owner when she went looking for it.)

      • 10

        Jessie says

        That did occur to me, Len. But it happened in New Jersey – here in South Dakota, the first person to see that ring would have turned it in.

  5. 11


    We have had so many of these. Fortunately, our tots don’t have cell phones yet – but we know what to expect now! Another big “duh” thing for us in the past was late fees. We were just not on top of paying bills on time for a while when we were both working and super disorganized.

    • 12

      Len Penzo says

      “Fortunately, our tots don’t have cell phones yet — but we know what to expect now!”

      Oh no … I don’t think you do, Wayne. I don’t think you do. LOL! 😉

  6. 14


    Well, we had a large number of mega ‘oops’ in the days of personal finance darkness. Overpaying for under insurance for ten years was a biggie; but nothing ever remotely amusing post-factum – just embarrasing, really. But…

    A friend of mine loaded all his maps, journey panning and what not on his phone and went to Australia. First day there, he went to the bathroom and dropped his phone in the toilet – iPhone ruined and holiday seriously hampered. Now, six years later, he can laugh about it.

  7. 16


    In our household, we never buy extended warranties. The manufacturer gives warranty for let’s say a year. The extended warranty does not start after the manufacturer’s expires. That would be nice if it did. The problem with extended warranty is that it always overlaps the manufacturer warranty.

    Many folks buy extended warranty when they buy a new car. Most cars have at least three year-warranty. The dealer makes money from the manufacturer on top of the extended warranty you buy.

    That should be heaven for the dealer.

  8. 17

    WB says

    We had an 89 Honda Civic with no extended warranty. At 38k the compressor died. When we bought our 2003 Civic the extended warranty was priced at about the same amount as the new compressor. So we bought the warranty. 148k miles later we have yet to use that now expired warranty.

  9. 19

    ME says

    I bought tickets to see the opening act, but the main act cancelled the tour due to medical reasons. The only way I could get my money back is if the main act didn’t reschedule. There was no way for me to know when they rescheduled, but the opening act would be different. I was only interested in the opening act. It cost me $169 in concert tickets.

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