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My Evening, Alone, at New York City’s Most Romantic Restaurant

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At 6:29 P.M. on a Friday night I arrived at one of New York City’s most romantic restaurants.

Alone.

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Willingly.

My notebooks and my drink (i.e. my companions for the evening).
My notebooks and my drink (i.e. my companions for the evening).

One If By Land, Two If By Sea (named after a line in Longfellow’s poem “Paul Revere’s Ride” and established in 1973) calls itself the “go to spot in NYC for engagements, anniversaries and weddings. More people are said to have announced their engagement here than any other restaurant in Manhattan.”

I do not know where it is “said” (and I couldn’t reach the restaurant to confirm; the manager was unavailable and they told me to call back after "the holidays"), but other sources, from New York Magazine to Yelp to Zagat’s to Architectural Digest concurred.

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A review on the site of the boutique travel company Compass + Twine pronounced that “the history alone”—OIBL,TIBS (my own abbreviation) is located in a 1767 building that was once Aaron Burr’s carriage house—“makes the place feel frisky.”

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The write-up continues: "Listen to the pianist tickle the ivories while you eat at this West Village restaurant that’s so infamous for romance (you’re pretty much guaranteed to see a proposal)." I'd never witnessed a proposal before. For my first one, I wanted to see the scene that would have happened had Elle, in the opening montage of Legally Blonde, received a ring instead of a letter of resignation.

The ivories were practically cackling (Pachelbel’s Canon) when I took a seat at the copper-topped bar. As soon as my eyes readjusted to the dimness, I noticed the exposed brick walls, the stained glass windows, the oil paintings, the broad wooden floor planks, and the wrought iron chandeliers (faux candles).

It was as if I had walked onto the set of Hamilton, one hundred years before electricity was invented.

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Over the piano, the group of four in the lounge area behind me discussed their favorite Bill Murray movies and their confusion surrounding doctors with similar names (Rosenberg, Rosenstein, Rosenblatt... who can keep track?). In the dining room, at one of many tables decorated with a pair of tall candlesticks and a centerpiece of roses—sat another group of four and, by the window, a sole couple.

Because I couldn't politely stare them down until the inevitable proposal (the Huffington Post reports that "if you're offered a special extra course 'designed just for you,' you'll likely be served a ring surrounded by rose petals served under a domed silver platter"), I turned my focus to the cocktail menu.

The first on the list was the Coupe d'Amour, a jack-of-all-trades love potion made with vodka, blood orange juice, passionfruit, hibiscus, and sparkling wine. Too proud to sip that alone, I had a Tail Spin (gin, green Chartreuse, Campari, and sweet vermouth).

Last Word
Last Word

By 6:38, nine minutes after I'd entered the restaurant, my drink arrived and the piano man had moved on to "Can't Help Falling in Love."

By 6:45, just as I was running out of things to look at, another couple arrived (his birthday dinner, his partner winked to the hostess).

By 6:47, they were seated and I realized I didn't know how to hold a coupe. From the stem? From the bowl? Was I really qualified to be assessing this restaurant's romance quotient?

By 6:49, I judged it was time to check emails on my phone.

By 6:53, I was tipsy enough to start taking photos of my cocktail but not enough to start singing along with “I Dreamed a Dream." The tuxedoed fleet of servers hummed the tune as they waited for the bartender to shake and strain.

At 6:55, the piano player keyed the first notes of “All of Me” by John Legend. Despite the romantic hypnosis that the song casts on all normally functioning human beings (what? only me?), at the table by the window, neither member of the couple reached for a ring box.

6:58 and I was joined at the bar by a married couple (I know this because her phone background was a picture from their wedding day). She ordered the Coupe d'Amour. I couldn't help thinking the most romantic night of their lives might have already passed.

Three more couples arrived by 7:09, but some were seated upstairs or in the back, where I could not monitor them closely. "The Hills are Alive" came from the piano.

7:13: I yawned. (I know this because I, diligent reporter, recorded it in my notebook.)

By 7:11, another solo-flier had arrived at the bar. He ordered a dirty martini with three olives in a British accent. We did not speak. We did not make eye contact, or even side-eye contact.

By 7:12, my dream of being proposed to by a total stranger in the most romantic restaurant in New York, shattered.

At 7:17, I only had thirteen minutes until I deemed it journalistically-appropriate to leave.

By 7:19, I switched from checking email (productive! work-related!) to checking Instagram (frivolous! disheartening!). "The Hills are Alive" had transitioned to "Edelweiss."

I had signed the check at 7:27. I glanced around the restaurant one last time, but not one person had taken a knee. Confetti was not falling from the sky. No one was sobbing tears of jubilation. The Harlem Gospel Choir was not bringing down the house.

At 7:29 (one minute too soon), I scurried out to the soundtrack of James Taylor's "You've Got a Friend" (...but not a romantic partner to share this evening with).

By 8:15, I was home, making a dinner decidedly less glamorous than OIBL,TIBS's signature beef Wellington. I could have lit a candle or put on the "Classical" playlist on Spotify, but there was no one but myself to kid.

Here, there wasn't even the possibility, however small, of domed silver platters or piles of rose petals or life-altering questions and answers or salmon en croûte. (But for that last one, I'm thankful.)

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The next night, my roommate went to OIBL,TIBS to celebrate her three-year anniversary with her boyfriend. This was no coincidence: It was she, who'd had her reservations for weeks in advance, who initially clued me in. She got her hair done and bought a special dress. She ate wasabi risotto (yes, wasabi risotto) and had a really good time, as she told me the next morning.

They witnessed a proposal at the table next to them, though the ring did not come hidden under a domed plate (or tucked inside a piece of cake).

It was a subdued conversation: None of the diners noticed until they saw the hug.