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Fries and Puffy Eyes: The Sherwood Diner

Photo courtesy of Getty Images
Photo courtesy of Getty Images

Lexi Preiser ’10

Photo courtesy of Getty Images
Photo courtesy of Getty Images

It’s 7:00 p.m. on a Saturday night. I am sitting in a window booth of the Sherwood Diner, eagerly awaiting my banana pancakes.

I rarely order dinner items at the diner. The diner is one of the only places where I can order breakfast 24 hours a day, and this is exactly what I do whenever I am here (which is often).

This first meal marks the beginning of several, as I have dedicated my journalistic skills to investigating the goings-on of a Saturday night at one of Westport’s most popular hangouts.

By 7:30 p.m., the dining room is filling up with children, teenagers, and adults. The teenaged girls are adorning cute outfits and straightened hair. They are buzzing with the excitement of the possibility of a “night on the town,” whatever that means in this town.

Four such girls, sophomores, sit down in the booth to my right. My companion (who I reluctantly convinced to spend six hours at the diner with me, on the promise of free food) and I cut off our conversation in order to eavesdrop, which isn’t hard as these girls are giggling and gossiping loudly.

“Oh my god, I heard that Jason is having people over tonight.”

“No way! I thought nothing was going on tonight. God, this town can be so boring. I wonder if Josh will be there?”

“Ahh! You want him so bad. I don’t really care who I hook up with, as long as it’s a junior. I just hope the cops don’t come this time.”

Ah, the optimism one feels at the beginning of a Saturday night! Anything seems possible­ as rumors of parties and crushes circulate around the diner.

Plates are cleared and bills are paid; fifteen-year-olds exit in a cloud of cloying perfume and flurrying text messages.

In rushes the second crowd of diners. This group is composed mostly of upperclassmen. A more relaxed group, they are a little less eager to scarf down their food and attempt to “go out.” Years of experience have stripped them of their Saturday night optimism.

It’s an accepted reality to these upperclassmen that they will probably end up hanging out in one of their friend’s basements, watching a movie. However, the night is young, and “we could always just crash that sophomore party, right?”

So, as my black and white milkshake arrives and the upperclassmen depart, the diner begins to enter a period of down time, usually lasting from nine until eleven.

This time is when teenagers have already eaten their dinner but have yet to consume their late night snack (or, to be a little less politically correct, they have yet to experience an attack of the “munchies”).

It’s 11:30 p.m. and we are back at the diner, after leaving our post for an hour. We are seated in the coveted circular booth in the main dining section, as our party has expanded to five people. Predictably, a few taxis pull up to the curb and the late night crowd starts pouring in.

Of course, there are a dozen or so intoxicated kids in the mix and one or two who run straight to the bathroom. Someone sitting near me orders chicken fingers, fries, and a short stack of pancakes. I peek over to notice that he has a content expression on his face and a set of puffy red eyes.

For once, I’m thankful that intoxication leads to loud voices, as I am able to attain the night’s scoop from a nearby acquaintance.

“I hate the cops. Why do they have to ruin everything? There wasn’t any beer left there anyways.”

So the night has proceeded into a classic case of a Westport weekend. Diner, party, cops, diner. Friends drift from table to table to share harrowing accounts of their narrow escapes. Others are merely returning from the movies or a family event, but all are interested in the night’s gossip.

Some sophomore girls squeeze their way into a table of senior boys. The room is loud now, and several kids wait in line by the door to be seated. Flustered waitresses deliver scrambled eggs and Cajun chicken wraps while adults cringe at the sudden increase in volume.

Two plates of fries, one stack of pancakes, and a milkshake later, my friend and I finally leave our post and head home. Despite a few humorous incidents, I have observed what I already knew. The diner serves as Westport’s social framework. It’s a meeting place for friends, a casual place to go on a date, and a late-night refuge for teens.

Plus, it has the best curly fries I’ve ever had.

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