Leftovers: When tipping becomes the tipping point

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Hands down, tipping remains the most popular, controversial, and debated subject I’ve ever written about.

The way a person treats a server or bartender is not always mirrored by their tipping practices, but the bottom line is exactly that: the server or bartender’s bottom line. Tips are the lion’s share of earnings for front-of-house restaurant employees. And tipping is a complex and compelling topic.

Historically, musings were most often along the lines of what constitutes a good tip? Or when is it really OK to leave less than 20 percent? What about the kitchen staff? What if I want to leave more (or more likely, less) than the automatic gratuity charge? Why should I have to tip on carry-out?

Questions were offered by servers and bartenders, too. During the course of countless slow shifts, my restaurant colleagues debated the merits of red lipstick versus a more modest shade, the pros and cons of smiley faces on checks, and other proactive tactics we might engage in to enhance generosity without being trampy or overly superficial. 

The guys among us had their own unique challenges: Should they make eye contact with the men at the table first? Should they dare try the smiley face on a check? 

Obviously, the best way to ensure a stellar tip is to provide attentive, efficient, and knowledgeable service. To recognize the uniqueness in each party as well as the opportunity to offer the best experience possible. Can the couple at Table 10 be upsold to a bottle of wine over single glasses? Does the party of six seem like dessert people? Proficient front-of-house folks know the drill. 

The reality is, there are few other vocations where financial ramifications rest on chance and a prayer for human decency. An experienced server can wear all the Robust Rose lip gloss they want, but if the guest holding the tab is a major putz, all is lost. 

Which brings us back to the here and now. The complete and total travesty brought about by COVID-19 starts at the top of the food chain with farmers and growers, to suppliers, vendors, middlemen, transportation, and so on, all the way to places most of us don’t even know to think about. There’s the company that makes biodegradable carry-out containers, the weekly window washers, the industrial uniform and floor mat cleaning company, all of them. Everyone. 

Along with the broken chain that includes my restaurant brothers and sisters, I am devastated.

As the devastation rages on, #neverthatkaren and my BFF urge me forward with positivity. It is with this same motivation in mind that I’d like to share the top three best tips of 2020, as told to me by people in the trenches. 

Jenny McCarthy tweeted this photo of husband Donnie Wahlberg’s $2,020 tip on a bill for $78.45 at the start of 2020.

1 — “A guy I had never seen before asked me if I had heard of the 2020 tip challenge,” a server from Portland told me. “It’s where celebrities leave a $2020 tip no matter how much the bill is. He left me $20.20 on an English muffin and tea. When he was leaving he said he was out of work and for us to stay strong. It was like $2,020 to me.”

2 — “My landlord carried out a cheeseburger last week,” a long-time bartender friend in Boston wrote. “He handed me something I thought was cash but it was a note saying he was waiving January’s rent. We hadn’t asked him or anything. I’m a grown-up and I cried for like 15 minutes.”

3 — “We’re on a rotating schedule to share shifts since it’s so slow,” said my former co-worker, Alicia. “It’s just me taking care of (Alicia’s 9-year old son) Marty and everyone I work with has given me one of their shifts. Amazing, huh?”

My own Top 10 annual best tips list used to be an irreverent blast. For a long time, the first column of each year told of “tips” ranging from skunky marijuana joints before it was legal, to a tattered St. James bible, to a gift certificate to another restaurant. There was a wad of cash and in 2013, someone gave me a pair of Red Sox tickets. 

Now, I wonder if the Sox will even play. I don’t smoke weed (it makes me feel funny), and as far as the tattered bible goes, I’ll take all the insurance I can get. 

The subject of gratuities never grows tiresome, but I’d rather discuss it when we all have full sections and a line out the door. Until then, please, do what you can to tip things toward the better and as always, enjoy your meal.

Natalie Ladd is a Portland restaurant veteran, freelance writer, and connoisseur of all things Bruce Springsteen. She loves Boston sports, chewy red wine and has never sampled a cheese she didn’t like. She can be reached at [email protected].