The restaurant overcharged them. The airline said he volunteered.
Two stories about how quickly everyday situations can turn messy, and why asking questions and keeping records matters so much.
Hi there, my friend.
I saw two newsletter posts this week that I knew I just had to share with you.
Both described everyday situations that turned sketchy through seemingly no fault of the victims.
In one post, someone was overcharged by a restaurant. In the other, someone was bumped involuntarily by an airline.
Let’s get it into it…
The case of the mysterious restaurant overcharge
My friend Bobbi, a certified financial planner, author of multiple books and creator of the “Financial Wellness by Bobbi Rebell” Substack, went to dinner with her husband and another couple the other night.
Lovely night. Good food. Good company. The kind of evening where you are absolutely not thinking about… math.
That’s where the problem came in. The two couples each handed over a credit card and asked the server to split the check evenly.
She did just that. However, as Bobbi says in the post, when the server handed each couple their bill, “the math was not mathing.” The two bills were for the same amount, but that amount on each bill was $20 more than it should have been.
I’ll let you click the link below to read the full post and see how the story ends, but as the link says, she was warned not to mention the restaurant by name in her post to avoid being sued…
The big takeaways:
Trust, but verify. This story is just further proof of the importance of checking your bill before you pay it and asking questions about it if something doesn’t look right. Regardless of whether the overcharge was accidental or intentional, the last thing anyone needs to do these days is pay $20 more than necessary for anything.
Never be afraid to ask a question about a bill that doesn’t look quite right. You should always ask politely and nicely first — accidents do happen, after all — because you catch more flies with honey than vinegar, as the saying goes. If that doesn’t work, some additional firmness and persistence may be required, but it rarely goes beyond that. Just being willing to push back on their initial response to your question often gets you where you need to go. That was true for Bobbi and her friends, but she never would’ve gotten there if she hadn’t taken the time to check the bill in the first place.

The case of the not-so-voluntary bumping
The other post I read was far more concerning. It was written by Christopher Elliott, an author, consumer advocate and journalist with whom I’ve spoken many times over the years, and I first saw it promoted on LinkedIn with the headline: “American Airlines claimed I voluntarily gave up my seat, but that’s a lie.”
In the post, Elliott tells the story of Charles Shearer, a man attempting to fly with his wife and son to his mother-in-law’s funeral in Japan. However, before they could board the first leg of their journey from Cleveland to New York, he and his family were pulled out of line and told there was only one seat available for the three of them.
Things got really messy from there, with much of the discussion centering around whether Shearer had been bumped from his flight involuntarily or not. Shearer was adamant that he was. American Airlines, Elliott reports, saw it differently.
As Elliott wrote…
Welcome to the Orwellian world of airline bumping, where “involuntary” can magically transform into “voluntary” with a few keystrokes in an airline’s computer system. It’s a neat trick that saves airlines thousands of dollars per incident. And as Shearer discovered, it’s nearly impossible to prove otherwise after the fact.
I can’t recommend reading his post highly enough. After his wife took the last seat on the original flight, Shearer and his son did ultimately make it to Japan, though on a different flight that got them there seven hours after they had intended. However, the real journey happened after they got home: a months-long adventure in pursuit of the compensation they were owed for being bumped. (Spoiler alert: It is a lot more than they were originally offered.)
Elliott does a thorough job of laying out what happened, what rights people have and what people can do if they find themselves in a similar situation. It’s an important read because what happened to Shearer and his family could happen to anyone. Flights are regularly oversold, and people get bumped all the time, whether voluntarily or not, so knowing how to protect yourself if it happens to you is crucial.
The big takeaway: Document, document, document. Elliott lays out several important, practical tips in his report, but one stood out most to me.
Document everything immediately. Send yourself emails. Text family members describing what happened. Take video, if possible. The contemporaneous nature of these communications makes them powerful evidence later.
This is good advice most any time you’re negotiating. In my book, “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life,” I mention this many times. Good notes — who you spoke with, when you spoke with them, what they said and any other relevant details of a conversation — are protection. Whether intentionally or not, customer service reps can sometimes get their wires crossed, leading to you being told different things by different people on different days. Documenting your conversations can help you avoid that situation turning into a he-said/she-said debate that, honestly, you’re not very likely to win.
You don’t need to record audio or write down every word of every conversation. However, making note of key points is a very good idea. It can be hard to remember to do so in the heat of the moment, and few moments feel more heated than when you’re bumped from a flight against your will, but if you can keep your head as chaos unfolds around you, you’ll be glad you did.
Austin friends, see you on Saturday!
If you’ll be in the Austin area on Saturday, May 16, I’d love to see you at the Greater Austin Book Festival at the Central Library from 10 am to 5 pm.
I’m on a panel at 11 am, talking with several other authors about our publishing journeys. For the rest of the event, I’ll be signing books, telling people about Ask, Save, Earn, and generally spreading the word that you have far more power over your money than you think you do. Hope to see you there.
Until next time!
Matt

