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

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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 nine 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, Ariz. 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 401(k) 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 401(k) 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 401(k) 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.

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