I Brought My Mom And Grandma As Wing Women On A Blind Date

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I Brought My Mom And Grandma As Wingwomen On A Blind Date
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"I don't have to sleep with anyone, do I?" That was the only question my grandmother had when I asked, at her 80th birthday party, if she would be willing to be my wingwoman on a six-person blind Grouper date. My other wingwoman? My happily married mom.

For those of you who aren't familiar with Grouper, this dating app, before it shut down in 2016, let you set up a blind date with three strangers in your area.

You'd choose a day and time for the date you wanted to schedule, and Grouper did the rest: from picking the venue to making the reservation. It even set your reservation name under something discreet so you didn't have to tell the hostess what you're really there for.

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But wait, why was I doing this? Three reasons:

1. The app asked its daters to bring along two of their best wingwomen.

My mom and grandma are the best wingwomen I could ever ask for.

Not only are they always on the lookout for potential dates for me (they're still trying to get me to color my hair just so that I can meet the supposedly straight handsome hairdresser they both go to), but being around them always puts me at ease. Also, they're an awesome time. 

2. The ability to make the most of any situation is a quality that I find extremely attractive.

The way a person handles an unexpected curveball speaks volumes about their character, so I decided to do the pitching on this one to see how our dates would react.

3. I wanted to give my mom and grandma a taste of what dating looks like.

The fact that in just a few clicks, I can have a date set with three strangers on any given night in NYC is pretty wild, am I right?

A big shout out to my girl Challen, Grouper's founder, who worked with me to schedule and reschedule this date during the launch of their app while they were still working out the kinks. I doubt Tinder would have returned my texts if I had a date suddenly cancel.

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At 9 PM on a Thursday in the Lower East Side, my mom, grandma, and I arrived at the swanky lounge that Grouper chose for us, told the hostess the name we were given, ordered a round of cocktails, and took a seat.

Shortly after, a group of three guys showed up looking confused, but were then seated at the table next to us.

For a minute, I thought that maybe they had been the group we were matched with, and that they had decided not to go through with it. When I asked our waitress, she assured me that she was going to bring our group over when they got here and that she wouldn't let them chicken out. My kind of girl.

Finally, three guys showed up and were seated with us. I wish I had taken a reaction shot because the looks on their faces were really priceless.

My mom and grandma introduced themselves as Pam and Laura, and the men made their introductions as well (Brian, Tony, and Mike).

Tony made a beeline for the bathroom, where I assumed he was texting his crew to evaluate what to make of their current situation. But Brian and Mike ordered cocktails, and we started making small talk.

"So, how do you all know each other?" Mike asked us.

"We go way back," I told him.

Laura and Pam laughed.

"No, but seriously, you're not going to tell us?" Mike said.

"If you had to guess, what would you say?" I asked him, thinking our resemblance was pretty obvious.

"You're sisters?" Brian asked, followed by, "Where's your mom tonight? Does she know you're here?"

That got a good laugh from us as well. When Tony returned, he asked what he had missed, and Brian filled him on how we were related.

"Wait," Tony said, dead serious, "You're sisters?"

"Tony is our smartest friend," Brian told us, which made us all laugh again.

We had definitely lucked out with this group.

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My mom once told me the story of the first date she ever went on. Apparently, she had barely said a word the entire time, and her date broke things off the next day, telling my mom that she was too quiet.

That woman is not the same Pam who came out with me on this Grouper date. My mom was the star of this Grouper, telling the guys all about her restaurant business, her time running the Italian restaurant that my family used to own on the Upper East Side, and her future dream of owning a food truck.

My grandma is one of those people who has a way of making you feel good about yourself, no matter what. When you talk to her you feel like you're really being heard, and that what you have to say is interesting, even when you're not so sure that it is.

She worked that magic on our dates, asking each of the guys what they do, where they live, and what they studied during college, as well as the very important question, "Who here is Italian?" (only Tony, and only 1/8th — but she didn't hold that against him.)

As we listened to the guys tell funny stories from their college days, I felt more like I had a front-row seat to a sketch comedy show than the reality that I was here on a blind date.

As we started to like them more and more, my mom felt increasingly guilty that we were still lying to them about what was really going on here, and she made me spill the beans.

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"Wait, so you're not really sisters?!" —Tony

"Where's Ashton Kutcher, are we being punked?" —Mike

"My wife and kids can't know about this, where are you publishing this?" —Brian (He was kidding.)

Since our secret was now out in the open, I was dying to find out what they thought when they first saw us.

"Honestly," Tony said, "When we first got here I went straight to the bathroom and texted everyone saying... I'm really into Pam." Pam, my mom, insists that he was kidding, but I'm not so sure.

Brian told us that the three of them actually did have an exit strategy for if they wanted to bail; a nonchalant sign they were going to use to signal each other, just in case. When we asked him to show it to us, he made what looked like big S.O.S. circles with his arms in the air, which cracked us up.

We eventually called it a night and said our goodbyes. My mom handed out cards for our family's restaurant in Long Island and insisted that if the guys are ever in the area, they come in and let her buy them some dinner. I got contact info from all three of the guys... to send them this article, of course.

"So, which one are you going to text?" my grandma asked once they had left.

Honestly, I kind of assumed that after pulling a stunt like this, none of them would be interested in a second date. I mean, what if I brought my dad along next time or something?

Actually, after he reads this, my dad might want to have a few words with Tony...

But in all seriousness, I hope this isn't the last I've seen of Mike, Tony, and Brian, who are responsible for one of the best dates I've ever been on, hands down. And you know what? I think that they might just be saying the same thing about Laura, Pam, and myself right about now.

When it comes to family, I hit the mom and grandma jackpot — and that fact is never lost on me.

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Danielle Page is the founder of ThisIsQuarterLife.com, a blog dedicated to making your mid-20s easier to navigate. Danielle’s work has been featured on Woman’s Day, Mandatory, The New York Times, Thought Catalog, and Huffington Post.

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Editor's Note: This article was originally posted in February 2015 and was updated with the latest information.

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