My Lesbian OKCupid Date At The Yale Club


We got coffee about six weeks ago, so when Caroline texts me, “Would you want to get drinks this weekend?” I’m a bit taken aback. The first date went well; we spent about four hours discussing college, Simone de Beauvoir and primarily Paris, where we have both lived. She was, in a word, adorable: a teeny, brunette, pearl-clad, ex-dancer-turned-dyke, and I was totally into it. When she never texted me back after I proposed a second date, I figured she saw right through my desperate attempts to sound intelligent-er and wasn’t interested. I’m now pleasantly surprised to see that a) I was wrong, or b) she was desperate.

“I’d love to,” I text back. “Where should we go?”

“How about the Yale Club? They make great cocktails!”

My heart skips a beat and I immediately respond, “Sounds perfect! I’ll see you then.” I’ve heard fragments about the Yale Club here and there: that only graduates of Yale, Dartmouth and University of Virginia (plebeians) can join, that it’s the ultimate insider society of New York City, that it’s actually the center of the New World Order/illuminati. Wikipedia lists George H.W. Bush, Hillary Rodham Clinton (and her husband), John Kerry, and Gerald Ford as members. Considering I went to a college notoriously filled with Ivy League rejects, I’m giddy with subversive, resentful delight at the invitation.

Other dates I’ve gone on with people I’ve met on OKCupid have consisted of the following: getting drinks at a dive bar in the East Village/Williamsburg, getting drinks at some place a half-step above a dive bar in Park Slope, eating Mexican food, smoking weed and watching Netflix, shameless drunk booty calls. None of these dates compare to the Yale Club; none can even grovel at its feet.

“Good thing you’re a bougie lesbian,” my roommate laughs when I tell him where Caroline and I are going. “Any other gay girl in Brooklyn would be like, ‘what the fuck?’” Personally, I like to think there is a vibrant population of Brooklyn lesbians curious enough to sneak a peek into the safehouse of our nation’s elite. So on Sunday at around 6:00 (doubtless the sexiest time of the week), I hop on the F train and venture into Midtown.

Upon arrival, I sink into an oversized leather chair in the chandeliered lobby and wait for Caroline. I feel like I should have asked for my parents’ permission before coming here alone. I try to refresh my memory, thinking back to my last date with Caroline: she’s an only child of a psychologist and a dad who makes for very charming “Dad Stories.” She speaks much better French than I do. She lives in a one-bedroom on the Upper West Side. We did not kiss after our last date. We did not hug. I did not know what to do with my hands when we parted ways. Oh, God — did I wave goodbye to her?

Caroline arrives about ten minutes late and though her tardiness doesn’t bother me, I find her incessant apologies extremely endearing. (“Girl, you’d better think lack of punctuality aggravates me! It should, since I’m in THE MOTHERFUCKING YALE CLUB!” I say to Caroline as I pour shots for every retiree present, in my wildest fantasies.) Also, she’s straight up wearing a fur coat. Don’t worry, it’s reversible, so fur only shows at her cuffs and collar, but if she wanted to she could be that bitch in fur to the floor. I swear to God, I must be in the deleted lesbian plotline of Gossip Girl.

We get into the elevator and she presses the button for “The Grill.” I have not gone to a “Grill” since my friend’s high school graduation party at her grandfather’s country club in 2008.

Me: “So, what’s the deal with this place? Is it only Yale grads here?”

Caroline: “Yeah, it’s Yale, Dartmouth, and Virginia grads, and their kids, if they choose to remain members.” She does not mention any fees or underground meetings re: global domination.

Me (completely unclear on how to respond): “So uh, are there a lot of 20-somethings that go here?” (What kind of question is this?)

Caroline: “Not really.” The elevator doors open.

We sit down in two stately leather chairs; I feel like a pussy for not having a cigar in my mouth. The walls are plastered in game and portraits of old white men. A fire is roaring. It’s comfortable. There are complimentary Cheez-its(?). I don’t hate it.

I immediately browse the drink list. I consider the extent of Caroline’s tiny frame and predict she’ll order a glass of wine or a cocktail. I’m a beer girl myself, but I now desperately seek to fit my context. I mean, who of the <100 female Yale Club members describe themselves as “beer girls”?

After a few minutes of thumbing over the menu and daintily stepping towards conversation, a server arrives to take our drink order. “I’ll have the Yale Club Cocktail, please,” I say, failing to hide my cheeky smirk as the words linger over the table.

“And you, Miss?” the server asks Caroline.

“Oh, I’ll just have the Yale Club Lager, please.”

Great. Makes sense that the only Yale Club lesbian in history is, too, its only “beer girl.” Or maybe she sensed my “beer girl” qualities (leather satchel, staring in wonder at the various buck heads mounted to the walls) and, too, wanted to match me? But no, she wore fur to the date. There is no chance of Caroline trying to get on my level; the only choice is to rise to hers.

What’s more is that I didn’t really read the ingredients of the Yale Club Cocktail before ordering it (which likely speaks to why I didn’t get into Yale). So, upon its arrival, I find a martini glass filled with an offensively neon blue substance, which the Yale Club extracted from either Mars or a Sandals: Jamaica commercial. It may actually be Alex Mack goop of a different race. I look and feel like a certifiable asshat. Caroline sips the lager I yearn for. We carry on with the cumbersome conversation of any second date.

Me: “Haha, so I just got back to work last week…” (Side note: The electrics of my office building were totally ravaged in Hurricane Sandy. For two months, I was paid your precious New York City tax dollars to bullshit around Brooklyn.)

Caroline: “Wow, really? That’s crazy, how did you spend your days?”

I immediately begin to panic. Truth: for two months, I woke up every day after 11, thought about working out and didn’t, made either tuna salad or burnt kale for lunch, found an errand to do (buying new shampoo, getting posters framed) and took an exorbitant amount of time to do it (sometimes days), came home, gchatted for two hours until my housemates got home, bothered them for a while until they needed their own “me time,” went out to dinner /ordered in/ ate cereal, then watched My So Called Life alone in my room until 2 a.m. And repeat. But instead, I tell Caroline:

“Oh, well I tried to get up by 9:30 every day. You know, I just feel so much better having accomplished something before lunch,” I feel the lies tumble out of my mouth, wild and untamed, impervious to my attempts to wrangle them in. “Usually I’d work out first just to get it out of the way but, haha, I didn’t always get to it. I’d spend a lot of time writing, running errands, and I, um, I got really into cooking. I… cooked a lot. You know, like, food, and stuff, stuff like food.” She nods, “Yeah, I’d really need to make a schedule for myself if I had all the days free, you know? I’d go completely insane.” “Totally.” There is no way she believes me; she probably noticed I’ve gained five pounds since our last date. I take a sip of my toxic drink and wonder why no mini umbrella is sticking out of it.

We carry on. Caroline has lived in the city for a year and a half or so, though she spent time here with her family growing up. She’s finally begun to know New York on her own terms. “I’ve realized I’m just not a downtown girl,” she laments, in the least shocking self-discovery in human history. I jokingly liken Caroline to Brittany Murphy’s character in Uptown Girls; she does not laugh. I choke a little bit on my Yale Club Cocktail, mostly just to break the silence.

Caroline: “Are—are you OK?”

Me: “Oh yeah, cough, yep, sorry ‘bout that. Wrong pipe.” My Bulldog Flirtini is trying to sabotage me. I’m literally oppressed by the Yale Club. Is “wrong pipe” even a thing people say in New Haven? Caroline seems unfamiliar with the tight-chested breathlessness I now experience. Do Yalies not even have a “wrong pipe”? Are all their pipes correct?

I choke, hack and phlegm my way through the rest of our conversation about Museum Mile, and how really, nothing compares to the Musée D’Orsay’s impressionist collection, and next time you’re in Paris you must visit the Palais de Tokyo, as its new director has given the space a more dynamic aesthetic and has transformed the collection into a springboard for up and coming Parisian artists. I realize my inability to breathe is actually very convenient. (Even if I did have full access to my lungs, I would still be silently nodding along and turning red in the face.)

After about an hour and a half, Caroline tells me she has to cook dinner for her “best friend” (who she talks about so often, I’m confident they’re in love). I figure this is just an excuse, that she isn’t into me, which I accept. We don’t kiss goodbye, though we both enthusiastically say we should get together again sometime. We hug, and I feel like I may accidentally break every bone in her body as we do so. I walk to the F train and giggle to myself on the subway home, enjoying the aftereffects of my Yale Club Cocktail.

A few days after the date, OKCupid informs me that Caroline has recently looked at my profile. Still got it! 

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