Sure, we’ve all heard of the dating “social club” known as Grouper — but not all of us have done it. The dating site, which sets up a drink date between two groups of friends (three guys and three girls), has become pretty popular in Boston. After hearing all about my friends’ experiences with the dating club, I was intrigued and wanted to learn more. I wondered, is this Grouper thing really for everyone? What should someone expect when going on a Grouper date?

But I wanted a Boston guy’s perspective.

Luckily, I found a local dude who was willing to tell me about his Grouper dating experience. He’s a twenty-something young professional living and working in Boston. For the sake of the other people on the Grouper date, he preferred to remain anonymous. Here’s his story.

Why did you decide to do Grouper?

I was single and I had never done online dating before, it seemed like such a hassle to have to pick a site, make a profile, come up with a bunch of parameters to filter on, etc. A friend asked me if I was free to be a wingman one Thursday night, he had already arranged the time and place through Grouper. We all met at M Bar at the Mandarin Oriental in Back Bay. All I had to do was say yes and show up. It seemed like a good chance to wingman for a friend, try something out with a new social dynamic, and maybe meet someone interesting … why not?

The Huffington Post claimed that you can meet people “less awkwardly with Grouper.” Did this ring true for you on the date?

No question. The best part about Grouper is how different the flow of conversation is relative to one-on-one dating. On a date it’s usually more of a question and response pattern, with stiff structured dialog. Whereas, the conversation on a Grouper felt a lot more natural.

I think the 3-on-3 format is a perfect formula – not too many people that a group conversation is too chaotic, but also enough people that you can have a side conversation without feeling like you’re leaving the others out. But the four tag-along friends were definitely more at ease than the two matched people. It’s almost like they came to the high school prom together and weren’t sure if it was OK to ask someone else to dance.

Ok, so we all know Grouper is when three girls and three guys meet up at a bar. But what actually happens during the date?

We’d been told beforehand to prepare “Two truths and a lie,” although I don’t think we got through all of them because the conversation kept up on its own.  My “lie” was that I’d won a piece of the Argo Crag on Nickelodeon G.U.T.S. I think I immediately became less interesting when it emerged that it wasn’t true. It was good to have something to fill those gaps, so credit to Grouper for pushing that.

Tell me about your overall experience on the Grouper date.

Being with two friends brings out the “real you” as opposed to a false dating front, so to me there’s humor to be found in that authenticity. We went to a hotel lounge place, and I’d come straight from work and was starving so I ordered myself a big appetizer plate of lamb lollipops, to some quizzical looks. Meanwhile one of the girls mostly just expressed her wrath at the bartender who made her Negroni without the optimal amount of Campari.

So right off the bat there, I think it was established that we had very different degrees of taking ourselves seriously and wouldn’t be much of a match. But that might not have come out as clearly if we were on a dinner date one-on-one talking about generic stuff like our jobs and where we went to school.

What happened at the end of the grouper date? Was it awkward?

We did this awkward thing where everyone walked outside and wondered how to lay the groundwork for potentially hanging out again.  I’d guess there were some people hoping to maybe narrow down their focus onto someone specific but we just agreed to try to round the group back up another time using the two people who had been matched on the site.

We tried getting everyone back together again but couldn’t schedule it. One of the guys on the date ended up meeting up with one of the girls again, and I believe they each brought a new friend or two along – a rogue little Grouper of their own. So from that one initial match, there were a bunch of different possible dating combinations introduced to each other.

Who do you recommend grouper dates for? Do you think Grouper is for everyone?

Grouper is probably for you if you’re more clever than you are good-looking, since people seem to be superficial when choosing their traditional online matches. And it’s good if you have the kind of friends who bring out your best side. Just remember to bring along two friends who are slightly less attractive and funny than you are – you’ll shine. Because truth be told, it’s all relative.

Would you do Grouper again and why?

I was lucky enough to meet someone through friends shortly after my Grouper, so I’m happily out of the dating game. But had that not happened, I would definitely have done it again. Overall, I’d say it was a good experience – and the girls on the date (who were online dating veterans) said it was the most fun experience they’d had.

Photo courtesy of Grouper.com