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Where to Go on Your Last Date

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There are lots of magazines telling you where to go on your first date. Here’s a guide on where to go on your last.

Last Friday night, I was wandering around the West Village, trying to find a quiet place to break up with my boyfriend. Bars were too loud and too crowded. Restaurants were too quiet and fraught with various sharp objects. Desperate, I led him to Washington Square Park, but even there my attempts were thwarted, as the warm weather had brought out droves of musicians and skateboarders and mariachi bands intent on blocking the demise of my relationship.

I ended up finally blurting out the words on the 8th street subway platform at 2 a.m., which was the worst possible decision, as we were then trapped in a sort of Beckettian nightmare, forced to sleepily circle around the same issues to an unabashedly eavesdropping audience, never knowing when the train would finally appear, my exes’ sobs punctured only occasionally by the homeless bongo player disapprovingly shaking his head and saying, “That shit’s fucked up.”

The following week presented me with an even greater dilemma, as I struggled to choose a place in which we could have the obligatory post-breakup-closure chat. As I pondered this question and Googled my options (for which the magical search engine had no response), I realized just how rife with implications the decision truly was. Where we went, what I wore, what we said, it all affected whether we'd be moving on or going home together for one last time. I considered four distinct possibilities and what they meant. And for the New Yorkers, I included some helpful suggestions for local spots to get that closure.

1. A “let’s-pretend-to-meet-platonically-but-really-get-drunk-and-have-sex” bar

As a woman getting ready to see her ex-boyfriend, the moment of truth comes when you’re lathering up in the shower, and you are faced with the question of what (and how much) to shave. If you deforest your entire region, you have to be honest with the fact that you’re probably planning on having goodbye sex or seducing your ex into getting back together. Going to a bar that has emotional value for both of you (i.e. where you had your first date), will seem overtly emotionally manipulative (you don’t want to scare off your target).

It’s much better to go to a dive bar with enough cheap drinks to justify you doing the “Hey, what’s another beer between ‘friends’?” dance. Or go to an unassumingly romantic bar with a wine special, so you can drunkenly careen through the streets with your arms wrapped around one another in a way that inevitably ends with making out furiously and mumbling “Are you sure this is a good idea?” in the nearest bush.

Suggestions: Ayza (1 7th Ave South), with its candlelit setting and fine wine, and 206 Lounge (206 Sullivan Street), with its sparsely populated couches, can be great places to make your ill-advised move.

2. A “let’s-stare-out-the-window-forlornly-and-part-ways-warmly” diner

If you’re sans salacious intentions, and you really do want to just have a satisfying heart-to-heart, a diner might be your best bet for two reasons. Firstly, it provides a sort of cinematic ambience, and the heartbreak of parting can be significantly eased by pretending you’re in a movie, the stirring of spoons in white coffee cups and the diffused light creating the perfect setting for those warm-hearted “Thanks for the love. Live and prosper” conversations you see in indie films. Secondly, it provides an easy get-away if the conversation turns rancid, and you can just slam down your mug, throw a few crumpled dollars onto the table, and angrily storm out without worrying about who pays the bill. No matter where you are, there are always tons of great diners to choose from, but it’s best to go with one with large windows, where you can mistily stare at your phantom reflection in the glass as you sadly avert your former beloved’s gaze.

Suggestions: My personal favorites for this type of “I-love-you-but-I-just-can’t” conversation would be Pearl Diner (212 Pearl Street) or Square Diner (33 Leonard St) for their appropriately desolate surroundings and classic film noir feel.

3. An “I’ve-got-another-appointment-at-one-so-let’s-make-this-quick” park bench.

This one is serious. No one spends any lengthy amount of time on a park bench, so there’s an implied timer on the whole thing, which is nice if you’re the dumper and you just want to get it over with and move on with your life but panic-attack inducing if you’re the one who was dumped and know there’s nothing stopping them from suddenly stomping away forever. Still, park benches are to poetry what diners are to cinema (they’re where poets have always chosen to use bare trees to symbolize their unrequited love) and can therefore not only remind you that you’re not the first one to feel this way, but even inspire you to pen some angsty verse yourself. More importantly, the amount of space and fresh air around you serves as a comforting reminder that your life is not over, and that there is a whole glittering world out there left to date.

Suggestions: Sutton Place Park in midtown Manhattan has the romantic appeal of containing the bench on which Woody Allen and Diane Keaton’s character watched the lights of the Queensboro Bridge dim in Manhattan. And if you live in Brooklyn, the Coney Island Boardwalk is the perfect place to sit and stare poetically out into the ocean, your hands finding one another’s for one last sympathetic squeeze.

4. A “let’s-laugh-about-what-music-you-listen-to-and-how-you-snore” restaurant

So, you’re mature and you’re over it. To paraphrase Paul Simon, you saw your lover on the street one night, and she was so glad to see you she just smiled, and you want to talk about some old times and drink a couple of beers. While I think a restaurant is a bad choice for the recently abandoned relationship, as it forces you to sit through an entire meal together when the contents of the conversation might make you want to hurl (and affords little to no real privacy), it’s potentially optimal if you think the person is great but not for you, and just want to catch up and have a few laughs, leaving all memories of love lost to double entendres.

Suggestions: If you want to go with something classic, there’s nothing better than PJ Clarkes (44 West 63rd), the site where Alvy Singer and Annie Hall share a tender reunion in the iconic closing scene of Annie Hall.