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5 dates in 5 nights: Our spies test Grouper, Tinder & more

Grouper

Her rating: 3/5
Her review: Easy set-up, but it all went a bit haywire 

My "wing women" -- I owe them a drink.

Above: My “wing women” — I owe them a strong drink.

Getting started: Grouper is great because it’s basically a concierge service for dating. They schedule a date for you, pick a location, and send you friendly e-mail and text messages to make sure everything goes well. To set up a Grouper, one person, the “leader,” fills out a quick questionnaire to determine appropriate matches and then waits to hear about an availability. (The current waiting list is four weeks.)

The date: I recruited two wingwomen, Lauren and Amy, who both asked for some idea of what to expect.  As it turned out, even if I could have told them, we still would have been surprised. After I interrupted our perfectly pleasant, laughter-filled date to explain that I’d be writing about it for VentureBeat, the guys replied that they too had a secret.

Apparently the actual Grouper leader, John, had a girlfriend. When she found out that he was doing Grouper, she (naturally) freaked out and put a stop to it. At the last minute, he convinced his friend Nick to take over his Grouper. The only problem is that Nick, in his words, “isn’t exactly straight” and his friend, Akshay, is tentatively betrothed to a woman in India. The third guy, Remy, who barely seemed to know the other two, had been coerced into going and was a bit resentful, caustic even. (He told me I seemed like the kind of girl who was going to die alone.)

The aftermath: This night was incredibly fun in an absurd sense. It definitely will be a story I tell my brother’s future kids when I become an old, crazy aunt. Given how haywire it went, I’d be hesitant to pay $22 to go on a Grouper date again; meeting eccentric guys with zero dating potential is something I do very well on my own.

His rating: 3/5
His review: It didn’t quite live up to the hype 

Getting started: I was most excited to try Grouper. The startup has built a tremendous amount of hype by restricting access and sharing “groupergrams” of people having a wild time on their dates; one picture shows some fellas holding up their dates’ underwear. But in the words of Public Enemy, “Don’t believe the hype.”

Grouper was a good excuse to get my guy friends out on a weeknight

Above: Grouper was a good excuse to get my guy friends out on a weeknight

Upon joining Grouper, my dating concierge, Challen, set up a Grouper date with three girls, a few days in the future, location to be determined. I recruited two wingmen (both Safe Shepherd colleagues, Reid Cuming and James Slingerland). We filled out our profiles, and the day prior, received our location, Asiento. I had never been to Asiento before, even though it’s in my neighborhood.

Their party showed up on time, we had two rounds of drinks and appetizers, had a lot of fun, and decided to call it a night — they had to get back to the East Bay. At this point we revealed that James, my wingman, was gay, which they couldn’t believe. A fun night, and in Grouper’s favor, “not our usual Thursday.”

I decided to try again, and organized another Grouper date. This time, my concierge picked Dear Mom, one of my favorite bars. I picked Noah Sidman-Gale, a self proclaimed “bro,” and Eric Shen, who just moved to the city, as my wingmen — an eclectic party. Their party showed up on time, and things started off on the right track. An hour in, the momentum slowed, so Eric invited his backup-date to the bar. And then the Grouper dissolved into animosity. One of the girls revealed that she was in a relationship and not looking to meet anybody, and the other two decided that it was ice cream and parting time. Our bartender, the Grouper coordinator, explained that we did better than most Groupers he’d seen — the supermajority, he explained, end quickly and awkwardly after one round of drinks.

Everyone I’ve spoken to about Grouper (and most of my dates during this experiment) have had similar experiences. I’m not a dating statistician, but the odds of any two people liking each other are low; the odds of three pairs of people hitting it off seems orders of magnitude lower. I have many friends interested in trying Grouper, and I wouldn’t be surprised if they convert their hype into a large funding round, but one built on a broken premise. I would try Grouper again — but only to get two friends out of the house on a weeknight.

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