Grape Expectations (Or When Doing Good Goes Bad)

I’m on a mission. Navigating the waters of my existence like a swashbuckling sailor, I’ve let feelings guide me instead of following some reliable, boring North Star. And what I’ve discovered along this mission is that it feels good to make someone else happy.

So, with my boat lilting against the early autumn wind, I took off in the direction of a newfound quest for altruism.

If any of this is coming off as overly sanguine, I don’t mean to discuss seeking happiness for others in any kind of gloppy way; there’s a real sense of fulfillment that huddles deep in your belly when you do a thing, unprovoked, because you know it’ll make someone else happy.

Another related truth: Several of my close childhood friends have birthdays in early October.

The journey toward benevolence then found me contemplating how to best celebrate these friends’ birthdays even though they’re living in New York City and I’m in Southern California, thousands of miles from their lunch dates and dinner parties.

AHA, technology! I sent money to their boyfriends to pick up favorite desserts; I made collages of our best times together to post in commemoration of their special day; I ordered flowers, cupcakes … this was working! Until it wasn’t. In all my calculations, one of the birthday lunches I’d planned to help fund took place an hour earlier than scheduled. Not a big deal except it meant the money I wired via Venmo was now useless. Cinnamon scones had already been eaten. Coffee cups were drained dry.

Then, an idea struck. It just so happened that this particular friend mentioned to me she was having a birthday lunch and dinner. I even knew where she would be eating, a small, well-known Italian spot on NoHo’s Bond Street. When I called the restaurant, the woman at the other end of the line found the reservation with little delay.

“Great! Is it possible for me to buy a glass of wine for my friend and her husband? They’re celebrating her birthday, so a card would be nice, too.”

“Yes, of course,” purred the hostess. “I’ll send you our credit authorization form and fill it out with the amount you want to spend and your message.”

Life was rosy during the Afternoon of the Credit Card Authorization, when I filled out the form for $35, boldly circled wine and finally wrote a note signed by me and my dog: “Happy birthday, cheers!”

Everything was set. I imagined the candlelit scene where, over tiny cheese gnocchi and upscale meatballs, my friend would be surprised to discover the wine she sipped came courtesy of her California friend and an 11-pound terrier.

But here the story twists with a single text received: “THANK YOU!! You’re amazing! But are you sure?????? Can I maybe give you some money?????? I don’t know if you really meant to send this??????”

Definitely did mean to send, I wrote back, assuring her she should enjoy my $35 worth of wine — price not included in reply.

“Wow, thank you!!!! You’re seriously the best. I don’t even know what to say but I LOVE YOU!!!!”

K wait.

I love my friend, too. Except for wine worth $35 split between two, I’m not going to pen a Great American romance novel of platonic admiration and excessive exclamation points.

The next move was a call to American Express, asking about the most recent charge on my card.

Answer: $163.

Uh oh.

The moral dilemma stretching before me was clear as a glass of chilled Chardonnay. Either I tell my friend (who was at this point back home) that yes, she could actually send me upwards of $100 for that wine or I call the restaurant, find out what happened and untangle the mess.

In the realm of my misfortune, the hits just kept on coming. Without surprise, the fancy restaurant was unwilling to rescind the charge — “You wrote $35 and circled wine. We assumed you meant $35 of gratuity on whatever bottle of wine was chosen.” — and the issue escalated to the Director of Operations who would call me back with a decision. (He never did.)

I reasoned that honesty is in a long-term relationship with selflessness and told my friend about the mix up. She laughed, we laughed and that was that. A deed done with magnanimity at its heart, I decided, was no less worthy if it couldn’t be completed. Thoughts kindly formed are still formed in kind and unlike the $163 charge that AmEx dismissed, this story would live on.

– @melissakandel