The Gaggle Girls’ Most Memorable Valentine’s Days

When a book comes out that redefines a word and introduces a new perspective on dating, the world takes notice; the book gets written up in the New York Times, covered on CNN, and becomes the bedtime reading of singles everywhere. The phenomenon: The Gaggle: How To Find Love In A Post-Dating World. Written by Jessica Massa (pictured, left), The Gaggle says that because we’re in this post-dating, technological world where everything and nothing is a date, every guy in your life—in your “gaggle” (n.) of guys—plays a role and fulfills a need. From your spontaneous neighbor across the hall, to your intellectual friend at the coffee shop, all of these people, many of whom you’re not romantically involved with—covet some kind of quality that’ll guide you toward figuring out what you really want in a relationship.

Jessica—along with Rebecca Wiegand (pictured, right), her longtime best friend and co-founder of The Gaggle bloghas classified the gaggle into 10 distinct, highly-recognizable types of guys, from The Ex-Boyfriend Who Is Still Around, to The Ego Booster, to The Prospect You’re Not Sure Is A Prospect. And of course The Super Horny Guy Who Happens To Be Around A Lot. When you really take a step away from your interactions and take an honest look, it’s simple to pinpoint each of these men in your life.

The best part about The Gaggle: it makes dating—even simply hanging out with guys—fun again. As a single, 24-year-old girl living in NYC with a gaggle, I can attest that this book has powerfully transformed once pressure and expectation-laden experiences with guys, into carefree, “just enjoy what makes you happy” moments of glee.

In honor of Valentine’s Day, Jessica and Rebecca share their most memorable Valentine’s Days ever, from middle school on. And these girls delivered. From black lipstick, to messages on AIM, to psychic predictions, these experts on love have lived and learned. Here are their stories.

Jessica Massa:

1996: Valentine’s Day was a VERY big deal at the middle school that Becky and I attended. Within the hot and heavy world of 7th grade relationships, various school clubs had a tradition of letting students order roses and candygrams to be delivered to their admireree’s classes. This, of course, added an air of popularity, competition, and stress to the holiday. Every time the gift deliverers would interrupt a class with a rose, all the girls’ faces would light up in nervous anticipation: Is this one for me? Who could’ve sent it? Wait, no, why is Marissa getting another one??

That year, a few friends and I decided that we were going to rebel against the oppressive tyranny of Valentine’s Day. So we did what any other middle school girls would’ve done when Alanis Morissette was popular: we dressed in all black, piled on layers of black lipstick, and carried around bouquets of dead black roses. Take that, Hallmark.

Of course, this lasted until 5th period, when it turned out that a very sweet guy friend had sent me a flower to be delivered in math class. I couldn’t contain my huge smile. I conveniently left my dead roses back on that math class desk and walked around with my blooming red one all day instead. The black lipstick got rubbed off pretty quickly, too. I guess this was the year when I discovered I wasn’t quite the raging, idealistic, anti-love feminist that I’d been selling myself as.

Mid-2000s: God bless AIM. This year, I was sitting in my cubicle at work with no plans. By this time, Valentine’s Day was really a take-it-or-leave-it holiday for me—and with no serious relationship in my life, it felt like barely a blip on my radar. 

But then a guy who I had a little crush on IMed me. While we chatted about nothing, it came up that I’d be running a work errand right by his office later in the day. Cool! He’d come downstairs for a minute and say hi!

So he did. We ended up meeting for a drink, and then seeing his friend’s show, then getting food, and then wandering around the East Village, and getting another drink…it turned into one of those epic, aimless, unplanned nights where you find yourself enjoying each other’s company not really wanting it to end, so it doesn’t. No, we didn’t kiss that night. But we kissed later, so that was okay. 

This became one of the memories that I always looked back on, especially when Becky and I were first exploring the idea of a post-dating world. Had I wanted or expected dates, flowers, and proclamations of love, that night would have been a let-down. But by being open to any sort of fun, positive way to spend the holiday, I ended up with a really special memory of a great night with a cute guy.

2010: At a certain point of adulthood, you find yourself at peace with Valentine’s Day—relationship or no relationship. One of my best girlfriends and I decided to celebrate our utter lack of caring and concern for the holiday in 2010 by throwing ourselves a traditional little date night. We got drinks, saw the movie Valentine’s Day, ate a classy dinner, and then went back to her place to watch Up and eat a lot of candy. The night was fun and lovely.

But what sticks out to me was our experience at dinner. We were having the best time—talking, laughing, gossiping, sharing food. And then halfway through dinner, the hostess seated a beautiful couple right next to us. "Okay," we communicated to each other through a series of raised eyebrows, "here is the part where we have to watch a couple be in love on this most ‘romantic’ day of the year. We’re ready for it." 

But then! They barely said two words to each other throughout the entire meal. They spent the whole time on their phones. We were actually pretty sure they were eavesdropping on our conversation, simply for lack of better things to do or think about. And both my friend and I were reminded that the very act of being in a relationship doesn’t earn you a prize, or a higher station in life. You make the best of whatever your romantic situation is. And that year—even on a day meant for couples—my friend and I were so happy to just have each other.

Rebecca Wiegand:

Circa 2003: "I don’t need a designated day of the year to buy you flowers!" my then-boyfriend said to me. He was on a roll: passionate, European, an ambivalent capitalist. I adored him and basically agreed with his assessment that Valentine’s Day was a manufactured holiday thrust upon us by greedy Hallmark. Still, I managed to squeak out, "Really? When was the last time you bought me flowers?" Dead silence in the room between us. It turned out that maybe a yearly reminder, courtesy of the Romantic Industrial Complex, wasn’t such an offensive idea after all.

2011: "GET YOUR GAGGLE ON!" Jess and I announced at our signature, Gaggle Valentine’s Day party, and I’ll always remember the damn important lesson I learned that night. We and our team wore white dresses and circulated the room as modern-day cupids, introducing men and women who wore nametags that said things like, "I Need a Career Booster" or "I Need a Hot Sex Prospect" for women and "I’m Your Career Booster" or "I’m Your Hot Sex Prospect" for men. The concept was that you should use Valentine’s Day to explore and expand your gaggle – not focus laser-like and neurotically on finding "The One." 

I had showed up at the venue stressed out of my mind, anxious about the party and—as always—thinking ten steps ahead to everything I felt I had to accomplish in the next six months (and in my life). I scooped up the nametag that said "I Need an Ego Booster" and started ranting about how I needed some guy, any guy, to be nice to me, lend a sympathetic ear, support all my goals and ambitions, and tell me I was doing alright. I was fed up and tired of playing games via text, via email, in person, over the phone, with men in general, and the one man in particular whom I really liked, but also knew it was never going to work out with. Why couldn’t he get his act together? Why couldn’t anyone give me what I needed?

Minutes later, my brother ambled up to the bar; quite my opposite, he is calm, self-assured, and reserved. He was wearing the nametag that said "I’m Your Ego Booster."

When I saw him before me, I almost cried and laughed. There he was, not only supporting me and our project, but also putting himself out there to the single ladies present as the sweetest of all the gaggle guys he could be. I was humbled: I had the world’s greatest friend and supporter right there, but I hadn’t thought to look outside myself and beyond the realm of my fucked up love life. Having gotten over myself and my self-created psycho-drama, I was able to have fun at my own party.

2012: "You’re going to be very fertile this time of year, but I just can’t tell if it’s with a book or a baby!" The astrologer shook her head apologetically while also grinning. I was with two of my girlfriends at our local bar, where they were giving out love horoscopes. I crossed my fingers and prayed the stars were aligning to bring about book success; The Gaggle was being published in hardcover that June. Yet, another part of me wouldn’t have minded if the other b-word came about. I had just entered into a relationship with a man who brought more happiness into my life than I could ever remember having before. A desperate, hopeful part of me wanted him to stick around forever. Later that night, he met us at the bar, two big bouquets of tulips crammed into his backpack. He hadn’t known they were my favorite flowers. I took it as a sign—whether we ever had a baby or not – that he was the man for me. Once again, I found myself thankful for unexpected lessons learned on Valentine’s Day.

The Gaggle

Follow Bonnie on Twitter here.

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