The Summer Job That Could Have Been

The Nautical Mile is eerily deserted come winter. Gusts of February wind blow through my damp, curly hair, which I chose to wear down for the interview. A new bar and grill, across from the Crab Shack, is seeking a hostess. Tim gives me a warm hello as I step into a cold restaurant that […]

The Nautical Mile is eerily deserted come winter. Gusts of February wind blow through my damp, curly hair, which I chose to wear down for the interview. A new bar and grill, across from the Crab Shack, is seeking a hostess.

Tim gives me a warm hello as I step into a cold restaurant that appears to be under renovation. I clutch my brown winter coat to my chest as he tells me to have a seat at the bar.

He studies my resume with confidence; with more confidence than even I possessed when I applied.

I have a feeling, and I could be totally wrong, but your resume, it screams hostess.

In my head, I’m wondering why he drew such a conclusion since the only experience I have is writing and internships in related fields. I waitressed, very briefly, a month prior, but that restaurant was not the right fit, and not a memory I hoped to recall.

Oh, really? I smile at him, wanting my tone to convey curiosity rather than doubt.

Definitely, he says. With writing, I assume you’re very verbal. And plus, in order to work front of house, you need to be in your head.

At that point, I let out a hearty laugh, relaying my tendency to ‘overthink.’

What I don’t say is that I’ve been exploring avenues that are less cerebral, but still, I kind of know what he means.


The Nautical Mile is Freeport, Long Island’s very own brand of summer. Nestled along the canal, the mile is a strip (that’s roughly a mile long, go figure) that features seafood restaurants, bars, boutiques, and winks to maritime decor.

The mile is boat owners who dock for lunch, doling out a hundred dollars on food and wine. It’s families with small children inside the ice cream shop on the corner, ordering cones of cookie dough and vanilla chip and cups of cappuccino.

The mile is men zooming by on motorcycles, their bodies covered in tattoos. It’s loud cover bands on Friday nights playing to a boisterous bar crowd. I don’t practice Santeria, I ain’t got no crystal ball. Well, I had a million dollars, but I’d spend it all. It’s tan girls in tight tops and short skirts getting drunk on Corona. Its tan guys with gelled hair getting drunk on Budweiser. Its those girls and those guys bumpin and grindin till two in the morning on the outdoor dance floor under artificial palm trees.

The mile is no New England charm. It’s no quaint seaside town. But it’s ours.

If I work at the mile this summer, I think to myself, I’d be part of its culture. Already, I was romanticizing the idea of it all. Already, I decided that I can be part of this slice of summer life.


On my first day of training, I discover that Tim is no longer there. I hear that there was tension between him and the owner; disagreements about management, debates about how to run the place.

I’m disappointed, of course; he was my cheerleader and eager to show me the ropes. The other manager, a perfectly nice guy, has more of a ‘figure it out yourself’ approach. More of a ‘here’s the concept, now execute it’ approach. However, I was determined not to be swayed. I would be a hostess.

In early May, the mile is slow. I stand for several hours making small talk with the young bus boys who are contemplating if they have to stay till close if nobody comes in. They playfully tease me for living in a middle class suburban town and not in the underbelly of Freeport. I’m not sure where they are going with this, so I move onto another subject matter. I ask for a glass of water from the bartender who asks if I want ice, and I say no thank you to save a few seconds of time. I really want the water. I watch the camaraderie between the other waitresses, girls who have been here before, who have waitressed for many summers, who are not writing everything down on post-it notes like I am.

If I yell at you, don’t take it personally, one nineteen year-old girl with a blonde ponytail says. It just means I’m frustrated and it’s busy.

I’d say a majority of the staff are young, most likely younger than me. But I get it, I’m new.


As we approached Memorial Day weekend, the infamous chaos of the mile begins to unfold. Normally, I’d be with another hostess on weekend nights, but on this day shift, I’m by myself, running around with menus and writing down table numbers and server rotations. There are tables inside and tables outside, which are supposed to be ‘family style’ seating. I’m beginning to see Tom’s original point. You have to be in your head to keep tabs. To oversee the flow of the restaurant in its entirety.

The day is fine, overall. I would acclimate to a system. I would work out a plan with the other hostess. But is the meager hourly wage worth the physical stress?

After my shift is over, I leave the restaurant and walk a few blocks in the sunlight, feeling defeated. My feet hurt, my head hurts, my stomach is unsettled. I’m not given an official ‘break’; you eat and drink if there happens to be a free moment to do so. It’s just how it is.

I go to a movie with my parents that night and feel particularly emotional during certain scenes and particularly irritable in the car.

Once I’m home, I break down. I know a job is a job, and I need a job, even a seasonal one. And I know I was always intrigued by the restaurant industry; I know that I like socializing with others, and I thought that, hey, maybe dealing with people will help get me out of my head. But I’m not exactly happy. And I know that as someone who’s already susceptible to not feeling well, I don’t need physical strain from a job as well. (Add the longer summer hours and summer heat into the mix, and I could foresee bouts of nausea and migraines.)


My time at the Nautical Mile didn’t last long. It was the romantic summer job that could have been but wasn’t.

Yet, I’m still glad I left my comfort zone, even if just for a bit, to try something different. I’m still grateful for the learning experience, because with any experience in life, there’s always the propensity to grow and be the best version of yourself.

And with this experience, I learned that as I continue to navigate my job search, I will set my sights on a position with a desk and a chair.