The Power of Generosity

The free dinner that changed my life.

This post was originally written on October 19th, 2017.

It’s Thursday night and I’m on vacation with my girlfriend. Around now I would start prepping my weekly Monday post on this recent trip through Newport, Rhode Island, Cape Cod, and Boston, Massachusetts.

I had it all figured our you see: I was going to write about what we did, the route we took, how much it cost me personally, and the frugal hacks I enacted along the way. It’s something I’ve done with pretty much all other travel posts.

But instead of focusing on the cents and the dollars, I’m going to talk about two people who made our vacation truly special. It all starts with a receipt:

Nothing special right? You might be judging me for the $9 Tiramisu and $3.50 Cappuccino, and after all, we’re talking American dollars, so for us Canadians you’ve got to add the 25% exchange rate premium on top of that. But that’s just a fraction of what went down.

At around 7:00pm tonight my girlfriend and I wandered aimlessly in downtown Boston, with no particular clue of where to stop for dinner. We zeroed in on an Italian small plates restaurant 15 minutes on foot from our location that seemed well-rated on Google and showed the “$$” symbol, meaning pricey, but not super unreasonable.

Upon arrival, we were shocked to see what felt like more of a “$$$” menu, one that would probably total $100 USD for the two of us. Also inside were servers and clientele so well dressed, it put my dirty running shoes, hiking pants, athletic base layer, polo T-shirt and backpack to shame.

“Do we go in? We’re dressed like sh*t,” my girlfriend said as we stared at each other nervously.

“F*** it, we’re paying customers, we can dress how we like.”

Tired and hangry, we somehow convinced the hostess to let us in and give us a table. Quickly, we poured over the menu, quietly calculating amongst ourselves if it’d make more fiscal sense to get the set menu for $90 or go à la carte for $80.

To save the $10, we went à la carte with the small plates of risotto, meatballs, salad, tortellini, roasted beets with swordfish, and a four cheese ball with two tap waters. I splurged and got myself a $9 beer.

“So tomorrow we eat cheaper, right?” my girlfriend asked me.

“100%” I replied.

After placing the order, we both ran to the bathroom and got changed. My girlfriend swapped her t-shirt for a sweater and I my athletic base layer for just the collared polo instead. It was the most nicely dressed we were going to get.

Then our waiter approached us and blew our minds:

“So, good news, there was a couple sitting at this table here,” pointing to the empty one right next to us, “They decided to pay for your meal. They’ve covered everything you’ve ordered so far, except tip. You can order more, but whatever you’ve already ordered, it’s all been paid for.”

In synchronicity, my girlfriend and I exclaimed “What?!” So many questions ran through our heads. Was this a Boston thing? An American thing? A common occurrence in this part of town? We were assured not.

My girlfriend and I stared at each other in complete shock because never once did we exchange a single glance with our former neighbours. All I recall was they were both 50+, the man was balding with a black or navy jacket and the woman wore a green floral dress. We didn’t even hear them speak so we didn’t know if they were Bostonians to begin with. I stood up to see if they were still outside, but the two of them were long gone.

We ate our decadent meal still not believing the generosity we received. It was all we could talk about.

All night since the dinner, I’ve been asking myself: who were these people and why did they do this? What’s their story and what made them want to buy a $90 dining experience for a regular couple like us?

My girlfriend and I have made a few hypotheses: perhaps they thought we were poorer than we were based on how we were dressed, perhaps they heard we were from Canada and wanted to show some American love, or perhaps at some point in their youth, an elderly couple did the exact same thing for them and this was their way of paying it forward.

I will never know why this couple elected to pay for our dinner. I don’t imagine I will ever meet the balding man in the black jacket and the lady with the red/brown hair in the green floral dress. All I know is that these two people made our night and our entire vacation very special. It meant for once, my girlfriend and I actually ordered (expensive) coffee and dessert with our meal. It meant we didn’t have that transactional pain of affirming the final bill that was larger than a three day food budget. And it meant that some people truly have gigantic hearts.

With our stomachs full, my girlfriend and I made a pact that if we grow old together, we will one day (or on many days), do the same service that this couple did for us.

In the scheme of things, $90 is nothing, especially for a pair of Canadians who don’t deserve this level of kindness. What it did do though was turn a regular night into something that I will remember forever. It reminded me that the small generous actions we make can have a significant impact, whether that’s tipping well for good service, buying someone a coffee, or paying for a young couple’s dinner.

Frugal, middle class, wealthy, FIRE’d or otherwise, I have realized that we all have the power to think beyond our own financial independence in the name of generosity. I certainly experienced the value of that tonight.

And finally: to the couple who paid for our dinner.  

If you’re out there, know we are grateful and that we will pay it forward. Your kindness will never be forgotten.

And if you somehow read this and wind up in Toronto: dinner’s on me.

Author: stretchingeverydollar

Starving artist to Debt Free MBA. Attempting to retire early.

One thought on “The Power of Generosity”

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