The Gaggle: How the Guys You Know Will Help You Find the Love You Want

The Gaggle: How the Guys You Know Will Help You Find the Love You Want

by Jessica Massa

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Who cares if he’s just not that into you? You’ve got a gaggle.

It’s easy to feel like your love life is nonexistent. You know you’re great, so why haven’t you been on a classic dinner-and-a-movie date since . . . well, forever? Because as it turns out, you are now living in a post-dating world, where the old rules for sex and relationships no longer apply. Suddenly, everything and nothing is a date. But this means that you have much more going on in your love life than you realize.

Think about all the ambiguous interactions you have with guys: from a brainstorming session with a coworker, to a drink with an old friend, to a late night Skype session with an ex who’s still in your life. Once you open your eyes, you’ll see that you’re already exploring all sorts of connections with the men in your life via these non-dates. And who are all these guys you’re non-dating?

Say hello to your gaggle.

The gaggle is the group of guys in your life who play different roles, fulfill different needs, and help you figure out who you are, what you want, and what kind of relationship you ultimately desire. Though no two gaggles are alike, there are ten types of men a gaggle might include, such as the Ego Booster, the Hot Sex Prospect, and the Boyfriend Prospect. Romance, excitement, self-discovery, love . . . all this will be yours, once you stop stressing about dates, labels, and expectations and start thinking of each man you know and meet as a potential guy in your gaggle.

In this clever and groundbreaking debut, based on interviews with women and men across the country, Jessica Massa reveals the ways in which the potential for love is all around you. The Gaggle is the ultimate guide to figuring out what you want—and finding your match—in a world that has left traditional dating behind.

Product Details

ISBN-13: 9781451657548
Publisher: Simon & Schuster
Publication date: 06/12/2012
Format: NOOK Book
Pages: 288
File size: 2 MB

About the Author

Jessica Massa graduated magna cum laude from Harvard with a degree in psychology. Her work has been featured in The New York Times, The Wall Street Journal, Elle, Variety,, The Times of London, and, among others. She lives in Brooklyn.

Read an Excerpt


How would you define your romantic status right now?

“Single. Incredibly, unbelievably single.”

“Ha! Well, it’s sort of up in the air.”


“In a relationship for—well, two months later we asked each other, ‘So when would you say that we started dating?’ And we were like, ‘Oh, New Year’s Eve, when we got wasted and made out.’”

“It’s really complicated. How much time do you have?”

“I’m on I was a little tipsy when I decided to do it. I wasn’t going on any dates, really—so I figured, why not.”

“I am in a very boring relationship with a man who is exactly like my mother.”

“I’m single. As of—well, I thought it was as of a couple of weeks ago. But apparently we weren’t even in a relationship! So I guess I’ve been single since November.”

“My romantic status… I would define it as, hmm, dating? Ish? Dating-ish?”

“Dating. Although we don’t actually go on dates, per se.”

“I don’t have a love life—I date gay men!”

“Completely single! Completely. But I mean, in the sense that, I guess I have been seeing people, but it’s not necessarily, you know…”

“I wouldn’t say that I’m dating around. I’m just trying to see what I like.”

“It’s a fucking mess, I’ll tell you that.”

When I hit the road and sat down with young women and men all around the United States during the course of a year, I started each conversation by asking one seemingly simple question: how would you define your romantic status right now? Initially I thought, no big deal. The question was simply meant to be a jumping-off point—a way to ease these strangers into opening up to me, and a clue that would help me categorize them into clear boxes (single, in a relationship, married, etc.) that would further direct our conversation. I was expecting one-word answers. Maybe five words, max.

As you can see, that’s not exactly what happened.

These varied, fraught, and uniquely personal answers made one thing clear to me—the times, they have a-changed. Gone are the days when one stock word or phrase could be used to sum up a person’s entire romantic reality. Ambiguity in our interactions and connections is now the norm, and thus, the traditional labels that we all supposedly know and understand now require caveats, qualifiers, embarrassed laughter, and crazy hand gestures to ring even slightly true. As it turns out, modern romance has gotten a little… complicated.

Blame the ubiquity of technology and all the miscommunications and mixed signals that it breeds. Blame the rise of the powerful modern woman and the insecurity of our male counterparts. Blame our Millennial Generation’s penchant for innovation and tradition breaking. Blame the disastrous divorce rates of our parents. Blame our childhoods, which revolved around participation trophies, parent-organized playdates, and consistent efforts to shield us from rejection. Blame reality television. (Why? Who knows—but it’s fun to blame it for stuff, isn’t it?)

Blame whatever and whomever you want. It doesn’t change the fact that the romantic landscape has changed—and we’re all standing in the center of it, trying to calm the storm just long enough to find love. Earth-shattering love, mind you. Because we’re Millennials. We don’t settle!

Luckily, this mystifying new romantic landscape is now ours for the taking. Yours, for the taking. So now I ask you, dear reader, just to start things off: how would you define your romantic status right now? In this very moment.

… Right. That’s what I thought. And no, “single” doesn’t count if you have to take ten minutes to explain what that even means to you.

There is a much more exciting romantic status out there waiting for you. An empowering one at that. So whatever your answer, ditch it!

Don’t worry too much about all the ambiguity for now. Once you figure out how to embrace it (instead of letting it drive you crazy), you will remember that finding love can feel like a fun and exciting adventure—not like an annoying chore to check off your to-do list or a frustrating goal to steadfastly work toward. Your love life will feel natural and comfortable and positive and enriching, and not like you are skirting a dangerous minefield where the smallest missteps threaten to blow you up at every turn.

So now, the moment we’ve all been waiting for…

Let’s start figuring out your love life.


I broke up with my last boyfriend to embark on this single journey, and I had absolutely no clue what I was getting myself into. I was like, “I’m going to find myself and become an independent woman and focus on me,” and it’s just turned into this big clusterfuck.

I thought it was going to be so much better! I thought it was going to be so much fun and I was going to be getting asked out on dates like every night, and eventually I would find a guy who I could date for a while—like on Sex and the City, all Carrie Bradshaw. And it’s just NOT. It’s not what you think it’s going to be, once you get yourself into it.

—Clarissa, 21, PR account executive, New Orleans

There is no shortage of advice out there on how to date.

Want to ace a date? Easy! Just spend as much time as possible up until the big night reading how-to articles, brushing up on self-help bibles, and frantically trying on dozens of cute-but-not-too-revealing outfits in front of your mirror. Dating is now presented to us as a scientifically provable formula. Do X, and he will respond with Y. Say Q, and you will ignite an evolutionary hormone in his brain that will make him think of R and react with S. Get a little adventurous by trying out Z, and he’ll go running and leave you alone and loveless for the rest of your life. DON’T DO Z!!!!

Need a refresher on some of these classic tips? Please, allow me the honor:

• Only say yes if he asks you out a few days in advance.

• When in doubt, wear red—it will make him think of sex (and how much he wants to have it, with you!).

• No getting drunk.

• Don’t talk politics, religion, or past relationships. Mostly just ask questions.

• Eat more than a salad, but avoid red sauce and garlic.

• Pretend to reach for your wallet when the check comes—but if he actually makes you chip in, what a douchebag! End this doozy of a relationship before it even begins.

• You can contact him afterward to say that you had a good time, but DO NOT suggest another date (that’s his job, obviously).

• Hold off on sleeping with him for… a very long time.

• Rinse and repeat until he declares his undying love for you. And then maybe you’ll even be engaged before your next birthday!

Like I said, easy.

You’ve got all this tangible dating advice right at your fingertips. You’ve memorized all the rules and adhered to all the tips, so… why does your love life still feel like such a confusing mess?

Oh, right. Because there’s one little secret that no one has told you yet.

All the dating advice out there is useless—because no one is really dating anymore. Traditional dating is all but dead. You are now living in a post-dating world.


A new romantic landscape developed in reaction to the strict rules, terrifying divorce rates, and now-irrelevant benchmarks of traditional dating culture; characterized by a generational embrace of ambiguous interpersonal connections and the rise of non-dates, techno-romance, and the gaggle.

Does that sound really serious? It should. A romantic revolution is taking place. Pick your weapon of choice, and let’s soldier on!


I think that the times are changing where you MUST “go out.” I used to ask girls on dates. I would be like, let’s get alone, let’s talk. Not to get in your pants, ultimately, but to get to know each other.

But now I think that’s inappropriate. There are a bunch of girls who I would just love to cut to the chase with and go on a date, but I just don’t think it’s done anymore.

What’s done instead? Fucked if I know!

—Bryan, 30, carpenter, New Orleans

Remember all the conventional wisdom that we just went over? Great. Now forget it! It was written for women who lived in a romantic universe that no longer exists. All that “advice” doesn’t apply to you—or the guys who you’re supposed to be “dating”—anymore.

Of course, you may find yourself on a date every now and then. But what you need to understand is that dating, in the standard, explicit, traditional sense, is no longer the primary path to love. Flowers, chocolate, dinner and a movie, classy Italian restaurants, expectations, labels, timelines… these well-worn symbols of romance no longer signify our main opportunities to find love. Dates are now the exception, instead of the rule. They have become one very small piece of the huge, mystifying puzzle that we call “modern romance.”

Look at your calendar. Do you have a date scheduled anywhere on there? Has a guy recently said to you, “It was great to meet you. Can I please take you out for dinner on Saturday night?” If yes, then, great! Make the most of it. Enjoy the free meal, and while you’re at it, have fun exploring the connection that you and this guy might have. But just remember, please, don’t look at him too intensely, order the spaghetti, or talk a lot. That’s just unladylike.

But any upcoming dates that you may have on your calendar are likely to be outnumbered by other types of plans. Happy hours at work, parties, soccer games, networking coffees, reunions with old friends, ladies’ nights out, business trips, concerts, dinner gatherings, conferences, sporting events… you get the point. And you probably think of these plans as part of your social life, or professional life, or personal life—as opposed to “dates,” which are supposed to be the most important part of your love life.

And here we have a problem.

Let me make a comparison. These days, expecting to find love by going on dates is like expecting to get in shape by going to a really hardcore spin class… once every few weeks. Sure, spin class is a step in the right direction. Of course, it can only further your cause. But one spin class every other Thursday is not going to lead you to your fitness goal all by itself. You need to get the rest of your life together and adopt a healthier day-to-day perspective as well.

Also, let’s be honest: spin class kind of sucks. Even though it’s good for you, some part of you is going to be dreading it, even as you get on that stationary bike and pretend to crank up the dial to whatever difficulty level the instructor is yelling about.

Nowadays, it’s the same with dates. In this post-dating world, dates don’t happen very often. And even when they do, they’re not guaranteed to be all that fun—or lead you to love.

There has to be a better method than dating for women to cultivate amazing connections with guys and find love. People are falling in love every day all around us. Often with nary an old-fashioned date in sight. So how are they doing it? What has replaced the culture of traditional dating?

The mainstream media has recognized that some kind of transition is taking place, with everyone from The New York Times to The Wall Street Journal to Glamour calling out the chaotic shift in the romantic landscape and shaking their heads at those crazy young’uns and their crazy cell phones. Those kids and their booty calls! And delayed marriages! And cross-sex platonic friendships! And refusal to be realistic and accept that relationships are mostly work and sacrifice and, let’s face it, drudgery! Haven’t they seen the reruns of Everybody Loves Raymond?

The complaints, judgments, and unhelpful warnings about modern-day romance are unending. But what about clear insights from within our generation? Where is the tangible advice for how to make the absolute most out of it? All that has been nowhere to be found.

Until now. Because luckily, you picked up this book.

We need, and we deserve, a coherent explanation of this new post-dating landscape. And we require a useful set of tools, language, and tips to clarify the confusion and help us navigate the post-dating world.

Let’s start with non-dates.

Table of Contents

Introduction: The Problem That Has Been Misnamed xi

Part 1 Welcome to the Post-Dating World

So Here's My First Question… 3

Dating 101: A Crash Course 6

Ding, Dong, Dating Is Dead! 8

Part 2 To Date or Non-Date?

Introducing the Non-Date 13

The Group-Non-Date 16

The E-Non-Date 21

The Friend-Non-Date 25

The Play-Non-Date 32

The Networking-Non-Date 38

The Surprise-Non-Date 43

"To Thine Own Self Be True…" and Then Let's Find Some Love, Shall We? 48

Part 3 The Gaggle Inventory

Fact: You Have a Gaggle 53

The Ex-Boyfriend Who's Still Around 60

The Super Horny Guy Who Happens to Be Around a Lot 71

The Accessory 79

The Hot Sex Prospect 89

The Unavailable Guy 101

The Ego Booster 111

The Guy Who Just Blew You Off 118

The Career Booster 134

The Boyfriend Prospect 144

The Prospect You're Not Sure Is a Prospect 153

WTF (Where the F*ck) Is My Gaggle? 161

Part 4 The Guy's Gaggle

Brace Yourself: Guys Have One, Too 169

But First, a Public Service Announcement 173

The Girlfriend Prospect 175

The Work Wife 180

The Short-Term Investment 185

The Last Resort 195

The Girl Who Is Out of His League 202

The Friend He's Just Not That Into 207

The Challenge 214

The Crazy Girl 220

The (Maybe) One 228

The Possibility 235

Part 5 Love in the Time of Twitter

It's Not Sexting … It's Techno-Romance! 243

Techno-Romance: Use It for Good, Not for Evil! 245

To Mom and Dad (and the Rest of Your Generation) with So Much Love: Thanks, but No Thanks! 249

The Relationship of the Future 252

In Conclusion… 262

Acknowledgments 265

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The Gaggle: How to Find Love in the Post-Dating World 3.8 out of 5 based on 0 ratings. 6 reviews.
Anonymous More than 1 year ago
If you are a woman who lives in a large city, is out at social events all the time and works and lives in an area with unmarried men, this might be the thump upside the head that you need. It was a total waste of money and brain power for me thought, and I stopped reading before the half-way point. However, if you don't live in an apartment, don't go out to parties all the time, don't have oodles of single friends, happen to work with people who are all married, or are not living on campus at college, this book will not help you at all.
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