It’s a Lifeless Void: An Interview with Sherry the Waitress

The raw transcript.

My notes from the interview, December 2025.

NEW YORK CITY 

Grace: I’m here with Sherry, a 63-year-old veteran waitress, living in Vermont. I met her at a bar during a trip down to the city where she was on vacation with her husband. We chatted, and she wanted to speak with me for the magazine about her life in the industry, considering we’re both dutiful waitresses. 

Grace: Years of sleepy small town diners and sleazy dive bars have worn on her body and spirit. In Sherry’s words, “…it’s a lifeless void. I’m in pain all the time, like I haven’t got any cartilage left in between my joints, and I get dumber by the day.”

---

Sherry: I used to be real smart, you know. I would do all this  math in my head, and could remember things easily. I felt so alert like a dog trotting around the restaurant. I can’t anymore. The other day I got my apron cleaned. Couldn’t even remember my own phone number to tell the lady.

Grace: I feel the same way a lot of the time too, like I’m wasting my potential.

Sherry: You probably are.

Sherry: The unpredictability of the days used to really excite me when I was a kid, like your age until I was maybe 30. I liked meeting new people every day, and I liked the dramatics of the business, like I had my own place to perform, with my tables and with my coworkers. I started as a waitress in my hometown – near New Orleans –  as a way to make some money before college, but I kept putting it off – different than you – and a different time too – I had an apartment and lived on my own right out of high school, but that was possible in the 80s. So when years passed and I was still making more money with my tips than my friends who had their degrees and their desk jobs and retirement plans, I just fucked off with the whole college idea. And I thought I was really smart for doing so –

Grace: I can relate.

Sherry: But now I really regret that. It’s thousands and thousands more expensive now to go to school. Even if I never used it, I wish I had my own degree. So I had some type of other option.

Grace: I mean you still have other options without a bachelors degree.

Sherry: No, I don’t. Other people in my place might, but not me, I don’t. I could never make it as a manager in a store or in a warehouse or as a receptionist. I really just don’t have the guts for it. People tell me, and I’m sure they tell you, all the time – ‘I could never be a server –

Grace, laughing: yes, always –

Sherry: ‘ – all the people and complaining you have to deal with. Honestly, good for you for being able to do that! Blah blah blah!’ I hate that shit I really hate it. Like they’re patronizing you. Social skills are a skill too, but people really treat it like it’s a gift or something. I don’t think I could handle trying a different kind of job and failing at it. I’m good at what I do.

Grace: I understand.

Sherry: They’re trying to be nice, but still I don’t like it.

Grace: Yeah. Did you ever have any really nasty customers?

Sherry: Oh yeah. At my first diner, it was a 24 hour place, I only worked the overnights a few times, but I remember them well. Our place didn’t serve alcohol, but lots of drunk kids and rowdy businessmen would come in late at night. I know that at some point the corner we were on became known as somewhere to go and pick up women, like, you know…

Grace: Sure.

Sherry:…and the men that would do that were really nasty but at least in plain sight they were nasty. In the diner, the normal guys who didn’t buy hookers were worse, so much worse. I was in my mid twenties, and they’d do stuff like shove their credit cards or cash into your back pocket just so that they could squeeze your ass, or they’d have you reach across the whole table to grab plates just so they could look down your shirt. I saw so many affairs happen, so many. And as the even younger girls circled through the place, teenagers working on their summers off and shit, the men would prey on them even more relentlessly. The younger girls who hadn’t been hardened by the public yet would fall for it sometimes, and suddenly they’d have a baby or a screaming wife in their face. The men always left them alone to deal with it of course. Sleeping with co-workers is bad, but customers might be worse. The worst encounter I ever had was with a college kid and his dad, both wasted, getting pancakes, and they were hitting on me and not letting up. I giggled and shrugged it off over and over, but eventually had to yell at them to get away from me. The dad got red and screamed at me, called me every name he could think of, and slapped me in the face. No one really cared. 

Grace: I’m sorry that happened. I worked at an ice cream place when I was 15. Stuff like that happened even at that age.

Sherry: And believe me, it was worse when there weren’t phones recording everything.

Grace: I believe you.

A drawing of Sherry, 63, a waitress at Suncrest Diner in Vermont. Illustrated by Amelia Stathatos. @lave.ndipity on Instagram

Sherry: When I entered my 30s, that’s when I started working at the bars, and I had seen enough of what happened with the drunks to prepare myself. And in these more sleazy places, you had a little more liberty to stand up for yourself. So I felt better. I made a lot more money too behind the bar, but I eventually switched back to serving. 

Grace: I worked at a bar when I was 17, it was kinda gross.

Sherry: The place I started at was disgusting. Just imagine the smell of the alcohol on the rubber bar mats, saturated to the point that it would just start soaking through. Really really cheap liquor too. I dealt with a lot of alcoholic regulars. I had customers who were basically yellow. It was really sad. The bathrooms were uninhabitable. There was an older man who worked as a dishwasher for a while, and after particularly long shifts, after handing the dirty dishes back and forth, the palms of my hands would itch because the guy had a constant fungal infection under his fingernails. 

Grace: Oh god…

Sherry: Yeah…But it was during that time, the fungus guy time, that I met my husband, so I remember it as a happy kinda era at that miserable bar. 

Grace: How’d you meet him?

Sherry, chuckling: He was actually a customer…I know I said that’s bad, and it is, but it worked out for us. He was a little older than me, 37 when I was 34, and he worked as a bank teller – he had a ‘normal job,’ which my parents liked. I had always dated the bartender artist types. During those times, me, my friends, my boyfriends, we would just drink all the time around town, and I was always getting my heart broken in some way. I had a coworker/ best friend once, when I first started at the diner in Vermont – she was dating another one of the servers, and he would just cheat on her over and over and over. And she never knew. No one ever told her. Everyone just kind of slept with each other anyway. There was a different set of morals that existed in the back of these restaurants. I think that people think they’ll grow out of the lying and the partying and the cheating once they get a “real job,” but many people never leave, physically or mentally. Anyway, Ricky – my husband – had asked me out while I was working a day shift behind the bar. He was celebrating a new job he had just been offered. Celebrating heavily. Him and his friends had racked up hundreds of dollars in shots and bar food, before the sun even went down. At one point in his stupor, he said to me, “you know what? You’re so pretty, I think we should just get married and you can come with me to Vermont and we’ll start our new lives.”

Grace: How romantic!

Sherry, blushing: It really was for me, even being so jaded by the drunk public. And that’s pretty much exactly what happened. At least, after a few more dates…

Sherry: But once I got married and moved, that’s when the ‘trouble’ with work kind of started. Where I started to feel like I was really getting stuck. I was with a nice man, who had a nice job, and we had a house, so it gave me the opportunity to relax. To be able to continue being a diner waitress, which was really what I loved at the end of the day. I could do whatever job I wanted since Ricky dealt with most of the bills. So I stayed – I’ve been working at this same place for almost 30 years now.

Grace: Wow.

Sherry: Yeah. At first it was great, I had what I thought was my dream job and my dream life. I was just addicted to that feeling of hard cash in my hand after every shift – that same high I got my first ever day working. And I was young and healthy enough to run around the place for hours and hours, and I collected story after story, regular after regular. I waited on celebrities that were on their way to glamorous ski trips, people on the run to Canada, regular old folk…I was really kind of enamored with the whole thing.

Grace: I feel like that, every day.

Sherry: But I stopped feeling like that one day. It started when there was a cook who seemed to have lots of medical emergencies, and also seemed very lonely. She had latched on to me a little bit, and had told me that her husband doesn’t really allow her to have a lot of friends. She had gone to the hospital one day for a cardiac emergency, and when she came back, I had asked how she was and she just unloaded onto me. About her medicine that she couldn’t afford, her hepatitis that she’d never gotten treated for, IV drug use, abuse – everything. And it’s like, you start to realize you can’t even do anything for her, because you guys are stuck, financially and physically at the restaurant. There is a beautiful sense of community you build from the service industry – I will say that – and maybe that’s all someone needs. Friends, and a sense of belonging. But there are so many assholes too. Eventually she left and didn’t come back. The other servers called her dirty and gross. It’s just like the performance with customers, your peers were performing in front of you too. 

Grace: I always kinda felt like everyone is pretty judgemental considering we’re all at the same shitty job or shitty restaurant.

Sherry: Oh yes. Unbelievable judgement. Again, it’s one of those things that you start to drown from if you don’t leave soon enough. So much misery and regret, people really resent honesty or success, even an attempt at it. I’ve grown up to be a bit nasty and bitter myself.

Grace: Hardened from that small world.

Sherry: Yes. Always on guard. Defending myself from drunks, from rumors. Instantly being suspicious of new employees when they first start. It’s like I’ve become the cranky old lady that I used to hate. I just assume the worst a lot of the time, because I’ve seen these lives play out in front of me. My coworkers, my customers. Dying from disease, having all this resentment for ourselves and one another. Kids they can’t take care of. Being objectified over and over and over again. Not to mention the physical wear on the body, the energy being sucked out of you. It’s a lifeless void. I’m in pain all the time, like I haven’t got any cartilage left in between my joints, and I get dumber by the day, doing the same performance I’ve been doing since I was your age. And so I just put up the walls, put on my face, and keep going. The restaurant industry forces you to stand in one place, like you can see all the decisions you made in the past, and all the things you could do in the future, at once. But you’ve built the walls in on yourself between the two. I’m very very mindful, always living in the present. But like the way a fossil does. Like I’ll just always be…there. I don’t feel like I can ever be malleable again.

Grace: I understand what you’re saying.

Sherry: Do you understand me?

Grace: Yes, I understand you.

Grace Stathatos

Grit Mag in New York