"Date intelligently!" proclaims The League, a new and highly selective dating app targeted at "elite singles" in San Francisco and New York. The League relies on LinkedIn data and "an advanced screening algorithm" to help determine who is accepted into the app and who stays on its extensive waitlist: Potential users are judged by their education and employment history in order to ensure they are "high-quality" enough to join the community of singles. (Once in the app, you can even further specify if you want the education level of your matches to be "highly selective" or merely "selective.") The ideal user is smart, ambitious, and successful, according to the app's website.
On July 31, The League held an exclusive party at the Surf Lodge hotel in Montauk, New York, promising great cocktails and an even better sunset. (For the uninitiated, Montauk is a newly hip vacation destination town at the eastern tip of Long Island, and the Surf Lodge is at the center of its young, trendy scene.) We were invited to attend and cover the event as press and arrived via party bus, though the vast majority of people on the bus were not press, just eligible members of The League. Brett had been on the app for a few weeks, whereas Jarry had it for only a couple of days, and neither of us was sure exactly what to expect. Here's what happened:
Boarding the party bus:
Brett: I went into this singles mixer open and optimistic, perhaps naïve, about how the night would unfold — but I did vaguely know what to expect. An app marketing itself to ~elite singles~ is going to attract a certain type of person, and I did not feel like that type of person whatsoever. I looked around the aisles and saw a sea of collar-popped finance/startup bros filling up the the seats and immediately picked up on the fact that I was in a different ~league~ than them. Although I'm usually quick to be social at events like these, I felt immediately more reserved and uncomfortable initiating conversations with the passengers around me. I didn't feel like I belonged there. One of the first lines I casually eavesdropped in on from a user was:
"Wow, that girl is like a model, bro. Well, like, a pretend model." He nudged a fellow League user and they chuckled together, flashing their Whitestrip-enhanced smiles. This was a bit of a foreshadowing of the rest of the evening for me, and only a taste of what was to come as we settled into our seats.
Jarry: When they told us the "party bus" was BYOB, some people decided to bring six-packs of beer, but I decided to bring low expectations. Unfortunately, my expectations were not low enough. Nothing I imagined could have prepared me for the actual hellhole that was this bus trip. First off, if I wanted to be surrounded by a sea of un-self-aware finance bros who live in Murray Hill for FIVE HOURS IN TRAFFIC, I would just move to Murray Hill. (I don't live in Murray Hill because I'm not a masochist.) If I ever hear someone say "DUUUDE!" or "BROOO!" again, it will be too soon.
Second, I have serious qualms about the lack of diversity on the bus (and at the party in general). There appeared to be only one other nonwhite person, but she was also press, so that doesn't count. Yes, you are more than welcome to create a dating app for "the elite," but not if it seems like "the elite" you are looking for consists almost exclusively of white people. This may come as a shock, but it is entirely possible to be a person of color and also highly educated and successful! This party tried as hard at being diverse as the finance bros on the bus did at talking about anything other than themselves... I'm sure you can guess how much that was.
The rest of the bus trip:
Brett: Around 10 minutes into the bus ride, the free bus booze was brought out, to my delight. I was MORE than happy to take full advantage in order to get through the next five hours of forced mingling. When they announced that they were going to start moving some of us around, I must have looked at Jarry like my eighth-grade teacher had just told us to find a partner for a biology lab. This was especially due to the fact that every guy around me looked like the kind of dude that picked on me for not being so great at kickball in middle school.
There were mimosas, bottles of rosé, vodka cocktails, and more. This part of the evening was actually quite pleasant and only helped to maintain my naïve optimism.
Jarry: At one point, one of the finance bros passed around a nude photo some poor girl had texted him in confidence. I thought that was an incredibly weird thing for guys who had just met to do (also, morally questionable), but perhaps I am blissfully unaware of bro bonding rituals. "Hey, dude I just met, check out this great pair of tits! They are really, really great. I am sooo horny right now. So, like, do you want to be friends or something? Sweeeet." Did I mention that we suffered through five hours of this? Have I emphasized enough yet how much of a literal hellhole this bus trip was? This bus trip was a literal hellhole. I'm pretty sure Dante once wrote about this bus trip and that's how we ended up with Inferno.
Arriving at the party:
Brett: Once we eventually arrived at the party, I was relieved just to see land again after the bus trek, so I was in pretty good spirits. This was also my first time in Montauk, so I was impressed with the lavish setup of fancy couches and pillows on the beach right by the shoreline. That, and I was very much into the chicken kebabs and sliders being passed around on tiny plates. This seemed like my kind of party.
For the first hour, there was an open bar, so I once again made sure to take advantage of it to get my fair share of mingling moxie via free drinks.
After a bit of settling in, I spotted The League's founder, Amanda Bradford, and left my newfound media friends to go chat. I sat on the rim of a couch and introduced myself: "Hey! My name is Brett — thanks for throwing this whole thing! I'd love to chat about the event and app if you have a second!" I was met with a preoccupied mumble and her turning toward the other people sitting beside her.
Well, maybe she was just talking with someone, I'll sit for a bit, I gathered. I sat there for a solid couple of minutes like an awkward goober, thinking she was just finishing up a conversation, until she got up and walked away. Admittedly, I was a bit thrown and baffled by the interaction — but I attempted to chalk it up to her stressing over organizing the event and perhaps being a bit frazzled overall.
Jarry: I'm much more of an elitist douchebag than Brett is (which is to say, he is not one at all), so I actually had a GREAT time at the party and I'm not even being sarcastic. It was like prep school all over again (if my prep school had zero diversity and bros with egos the size of Texas). But there was also free food, free drinks, free goodie bags filled with miniature skincare products — everything you could possibly want at a party in the Hamptons, and more. I particularly enjoyed the smell of the Montauk breeze, which was a nice mix of sea salt and entitlement.
Every time I turned around, yet another pastel polo or Brooks Brothers button-down seemed to magically appear. The party looked like a real-life Vineyard Vines ad but with fewer smiles. At one point, a strange man approached me and handed me a T-shirt, calling me a "beautiful petite," which is a nice thing to say about an object, not a person. A live band off to the side began to play what could have been The O.C. soundtrack, but people were too preoccupied talking about sailing and golf to pay much attention. As the sun set over the Surf Lodge, I gorged myself on lobster rolls and conversations about JPMorgan Chase and Citigroup that might fall under the category of cruel and unusual punishment for anyone who isn't a financial analyst. Only a handful of other women dared to touch the food.
"Tinder is lonely," one finance bro told me, explaining why he had joined The League, which is ironic when you consider that through its highly selective screening process, The League is by default the loneliest dating app out there.
The rest of the party:
Brett: Just 20 minutes or so after my initial awkward exchange, I ran into The League's community manager, Meredith. I had actually matched with her during my brief experience using the app. We'd had a few friendly and fun exchanges for a few days, which soon fizzled out when she cut off conversation and stopped responding. Ghosting's not a fun reality of modern online dating, but it's an all too common occurrence many of us have experienced.
A few of us were sitting together on the beach couches when she stopped by to check in on us. She made small chit-chat and asked if we were all having a good time — at which point she locked eyes with me, pointed, and said, "Oh yeah, I actually matched with this guy!" chuckling to herself before walking away.
I was a bit rattled and embarrassed by these two encounters, which did a good job of bringing me down to the esteem level of my awkward middle school self — so I was certainly socially hesitant and mentally checked out for the rest of the evening.
By hour two of the night, I was already feeling out of place and was more than ready to get THE HELL out of there. For a good hour-plus, I bounced back and forth between a bench close to the parking lot, where I was keeping a hopeful eye on the buses rolling in, and a couch right by the water at the furthest end of the Surf Lodge, used for prime sunset Instagram ops. I definitely didn't feel I could relate to the other partygoers around me, and I was essentially waiting out the clock until the night was over.
Jarry: Brett was visibly shaken from his failed attempt to interview Amanda Bradford, so I figured I'd try as well. The thing is, it's awfully difficult to find a blonde woman dressed in white when you're at a party in the Hamptons. After 20 arduous minutes weaving through a sea of Nantucket red, I found her with the photographer and asked her all about her brainchild.
Amanda emphasized that The League is absolutely not a one-night-stand community like Tinder, despite being dubbed "Tinder for elites": "When you meet someone on The League, it feels different. We take great pains to ensure that profiles appear respectful and high class, that people don't have photos that make it seem like they're partying and drinking all the time. It's supposed to feel more real, like these are the people you'd actually want to go out on a date with."
It's funny because after spending a couple of days trying the app myself, I was confident the self-declared finance bros in my inbox were absolutely not the people I'd actually want to date. The main profile pic of one bro in particular featured him kissing a Veuve Clicquot bottle larger than his entire torso; yet another's was a group shot of four naked men holding pumpkins over their dicks. High class and respectful indeed. And these photos definitely did not make it seem like they were partying and drinking all the time or anything.
As for how The League determines who can be let into the app, Amanda revealed: "We have an algorithm that shortlists people based on industry and age, because we want to give the community balance and diversity. We don't want all the guys to be in finance or all the girls to be in marketing. I do also have a team of people who review the profiles after the initial data screening."
It's funny because almost everyone I had seen on the app was a finance bro, so perhaps in an ironic twist of fate, The League's algorithm isn't even "elite" enough for itself. But does The League encourage elitism? Amanda had this to say: "I think that I'd rather be elitist than superficial, so if I had to choose between the two, sure, I'm elitist."
Brett: Had I not had my self-esteem-shaking interactions early on in the evening, I admittedly would most likely have had a much better time. Sure, I was surrounded by people who I felt out of place around, and who gave off a vibe of unapproachability with a tinge of superficiality, but the sunset was pretty sweet.
Though, I don't necessarily fault the people who download and try this app. In the dating landscape we're in now, where Tinder seems too sketchily casual yet Match feels much too formal, it's only natural to be curious about the latest app offering a new perspective, and a seemingly new dating pool. But rather than "dating intelligently," The League oftentimes feels a lot more like dating with a middle-school-esque exclusivity.
I should also mention that I deleted the app on the bus ride home.
Jarry: All in all, it was a great party with not-the-greatest people — the very demographic attracted to something like The League assured that. Because it's one thing to be an "elitist" who cares about a potential partner's ambition as evidenced by education and career, but it's another thing entirely to explicitly proclaim your elitism and automatically ignore those who haven't reached a certain level of socioeconomic success. The app self-selects for the latter kind of person. After all, it's not impossible to fall in love with someone who isn't as highly educated or successful as you are, especially because neither education nor career necessarily dictates one's intelligence or ambition — something The League forgets. (Not to mention how the opportunity to pursue higher education is often tied to one's socioeconomic class.) So, while The League says it would rather be elitist than superficial, it unfortunately manages to be both.
As we walked off the party bus to a block between 6th and 7th avenues, we passed by a string of 30 or so sleeping homeless men and boys. The contrast was absurd.