Confessions of an Anonymous Portland Waitress

I must begin with the most terrible, most humiliating secret of all: I am a waitress! I am yet another overeducated, underemployed, late-twenties-to-early-thirties Millennial that, despite all the initial promise of my generation, has found herself trapped in the food service industry even though I am, like, way too old to being doing this. The TV soundtrack goes wah-wah.

But it’s okay! Thanks to years of therapy, in which I have dealt with the fact that I’m surely letting my pulled-themselves-up-by-their-bootstraps Baby Boomer parents down, and thanks to the last legal drugs for those moments when all that therapy fails, I have come to terms with the undeniable truth that I actually enjoy being a waitress. I like it so much that I’ve stopped skirting the issue when people ask what I do. A few years ago, I would answer, “Well, I’m working as a waitress, but I’m looking for something better.” Or maybe, “I’m a waitress, but I’m really working on my short story collection.”

Now I’m proud of what I do. I say “I’m a waitress” with the smooth self-confidence Justin Bieber might employ to announce his arrival at a teenage girls’ slumber party.

Working as a waitress is the worst sometimes. Like, the Worst. I’ve been pitied by customers. I’ve been verbally abused. I once dumped a glass of ice water down a guy’s shirt and the embarrassment withered away a piece of my soul. But in spite of all the bad, I’d still rather work as a waitress than anything else. For those of you who’ve never worked in the restaurant industry and for those servers who need a reminder of why it’s great, here are the top five reasons I love being a waitress.

1. Working in a Restaurant Is Way More Fun Than Working in an Office. I speak from experience here. When I was still ashamed of being a waitress, I managed to get a “real” job. You know: Monday through Friday, nine to five, a title I could put after my signature in emails, full benefits, life insurance if the cold, utilitarian office environment caused me to push my emotions into my gut where they would eventually turn into colon cancer.

During the few months I worked in an office, I drank more coffee than I ever had in my life just to keep from falling asleep at my computer. Now I spend every workday meeting people from all over Portland and all over the world. They tell me travel stories and personal stories. They get loose lipped when they drink too much. There are regulars that have become my teachers, cheerleaders, and friends.

But the real fun, of course, happens with my coworkers. There isn’t a work environment in the world that can rival the unbridled, unfiltered entertainment simmering behind the scenes in almost any restaurant. My fellow servers and I share everything, from to self-deprecating high school memories to debates about proper pubic hair management to reenactments of fights with our significant others. The “Would You Rather?” games I’ve played with the cooks—ranging from “Would you rather get attacked by a shark or a lion?” to every ridiculous sexual scenario you can imagine—have had me laughing all day as I pick up and run plates to my tables. Restaurant crews are raucous, vulgar, direct, and too busy to waste time on political correctness. I’ve got no benefits, but being happy at work is my health insurance.

2. The Random Schedule. This one is probably a surprise to people with a more structured schedule, but I—and many of other servers I’ve talked to—actually love the weird hours. When I say I can’t go hiking on Saturday because I have to work, some of my friends rub my arm and say, “I’m so sorry,” as if I told them my dog died.

But I’ve learned to take advantage of my unpredictable schedule. I go to the supermarket weekday mornings when no one is there so I can choose a vodka sauce without having to squeeze my cart by that exasperated mother and her three kids, one of whom is having a meltdown in the pasta aisle. I’m so spoiled that I will do almost anything—make a meal with food discovered in the back of the cabinet, leave a burned out lightbulb in the lamp another day—to avoid shopping anytime there will be lines at the stores.

I can also make appointments more easily, whether they’re with the dentist or the massage therapist, because I snag all those Tuesday at ten am slots when most other people are working. I can walk to my bank, stopping for a coffee on the way if I’d like, instead of rushing there after work along with everyone else. And I might go out and get drunk on a random Wednesday because, if you didn’t know, it’s awesome to get crazy in the middle of the week and then have the good fortune to sleep off the hangover until the early afternoon.

3. Waiting Tables Is Like Tinder, but Better. I’m in a relationship now, so my restaurant-as-hunting-ground days are over. But in my heyday, I could flirt like a boss while remembering who wanted the top-shelf liquor in their drinks and who ordered their steaks how.

Any server worth her salt knows how to read people, which came in very handy when I participated in my own real-life Tinder swipes. This guy’s creepy, this guy doesn’t want to reveal he’s married, this guy is uninterested—but this guy, he’s a Goldilocks kind of right. In person, red flags are more obvious; you find out real quick if someone smells funky, for example. I’d get phone numbers and get asked for mine. The sordid results of these exchanges must be saved for a later time, so I’ll leave it at: My milkshake brought many boys to the yard.

An added bonus: Guys who are going to hit up your phone later leave huge tips!

4. I Can Make It Rain. I’m not wealthy by any means, but working as a waitress means I’ve always got cash on hand. Right now, I’ve got like 800 bucks in cash in a desk drawer. It makes me feel like a baller. There’s something so carnally satisfying about holding money in my hands. And then bringing it to my nose and smelling it. And then maybe rubbing my cheek with it. No one ever rubs their cheek with a credit card. It’s not the same.

At times, I dream of filling my bathtub with all my tip money and diving into it à la Scrooge McDuck. Which I have not done, but I could, and that’s wicked satisfying.

5. Sometimes I Get Mistaken for a Stripper. When I go to the drugstore to get overnight pads and a couple bottles of contact solution, and I hand the man behind the counter twenty-seven dollars in ones, and he sees the wad of dollar bills I still have in my hand, and he pauses to give me a once over, I know what he’s thinking: This lady might be a stripper. Which, frankly, at my age and my physical constitution, is a damn compliment.

I’m sure that, upon closer inspection, my unequipped chest and my un-French tipped nails send most people to the correct conclusion that, Oh, she’s just a waitress. But if even one Rite Aid employee in the city still believes I’m a stripper, I guess that’s alright.

Read Part II: The Most Annoying Customers
Read Part III: Favorite Customers
Read Part IV: Worst Customers