Why do we love stories about big tips? Because they restore our faith in humanity. On one hand, these are stories about “Cinderellas” whose customers become their fairy godmothers because they are deeply touched by how good people are at their jobs. This, for example, happened to Melissa Mainer, whose tip on top of a mere $3.45 bill was $20,000 left by her customer, a 92-year-old billionaire Benjamin Olewine, who wanted to help the girl pay for nursing school – her dream. It is always nice to hear that Good Samaritans can be found among the extremely wealthy and successful who aren’t doing it for the sake of publicity and virtue-signaling. They already have everything. There are also many stories about “fairy godmothers” who in fact aren’t billionaires or celebrities who (let’s be honest!) can afford it. For example, this story happened early in the pandemic. The 30-seat Hound + Bottle in Bremerton, Washington, was closed except for Fridays, when owners Jodi and Alan Davis started offering takeout dinners. One customer, a retired shipyard worker, routinely ordered online, picked up his food wearing a mask and slipped a crisp $50 bill across the counter.

“This went on for months, until the restaurant reopened for full service in July,” says Jodi Davis, who remembers the customer as a man of few words named Dan, and only because that’s the name he signed on his credit card slip. “It was huge. People like him kept us going.” Dan the Fifty Dollar Man, as he came to be known, put “wind in our sails.” Such stories warm the heart and remind us that although your tip doesn’t have to be enormous to make someone’s day, it definitely helps. No one would argue though that the number of zeros in such tales makes for a great story. One of those was even made into a movie: it was so like a romantic fairy tale with a happy ending. But it was all true.

The 1994 movie “It Could Happen to You” starring Nicolas Cage and Rosie Perez is based on a true story of Robert Cunningham who was a regular at “Sal’s Pizzeria” and his favorite waitress Phyllis Penzo who had worked there for more than 20 years. One day, instead of leaving a tip, Robert offers Phyllis to share a lottery ticket. They pick the winning numbers together. Several days later, Robert finds out that he has won 6 million dollars and calls Phyllis to tell her that 3 million of it are hers. The lottery pays them $285,715 annually for the next 21 years.

If you want to learn more about tipping etiquette, click here