The Love Gap

INTRODUCTION

hey girl, I understand you

The year: 1998. The film: You’ve Got Mail. So began my personal journey toward understanding what it means to find love as a modern woman.

It was almost Christmas, and I was still in grade school. My aunt was in town for the day, and my mom decided the three of us girls would go to the local theater and check out the newest rom-com—my very first rom-com. I was less than enthused. Maybe it was the title, and I just didn’t get it, but I distinctly remember tears were shed. “I don’t want to see a stupid movie about a stupid mailbox,” I said. (I’d seen the movie poster; there was a mailbox—that I was sure of.) My mom told me to suck it up.

I did indeed watch Meg Ryan and Tom Hanks fall in love on-screen that day, and thus skyrocketed into the ranks of die-hard romantics everywhere. Falling in love looked utterly magical—set against the backdrop of New York City, with someone who was so wrong yet so right—and I decided then and there that relationships represented an ideal worth pursuing.

At the time, I had this adorably naive idea of what my trajectory toward love would look like. I would “grow up” and meet my first and only boyfriend at age 16. In my dreamy, vivid inner world, he was going to be a modern-day Prince Charming type. He would be my safe place, the person to dry all my tears, someone with whom I’d “do life.” (I also imagined he would be incredibly witty, much like Tom Hanks’s Joe Fox in Mail, a coveted quality that refuses to die in my mind to this day.)

But then something really interesting happened. When I finally tallied 16 candles on my birthday cake, I had never had an intriguing dating prospect. Instead, I had gained an ambitious set of goals for my life that didn’t include a hero sweeping me off my feet. Friends, college, career, and my future felt far more pressing and real than any teenage relationship I might muster. I’d begun planning a path forward on my own terms, one where a magical prom date was secondary to finding a mentor or scoring a journalism internship.

I didn’t go to my prom, actually. But that same year, I did land my first freelance writing assignments, completely bypassing my internship plans.

See, somewhere around age 10, I’d brought home my first straight-A report card. When I surveyed those perfect scores, and my parents proceeded to sing my praises at home, that sucker was like a dopamine hit. I wanted more. Instead of ambling through life following whatever new whim was on my radar, I was suddenly serious. I studied, learned the meaning of delayed gratification, and made real goals for myself every few months—just in time for each new report card. I never got a B again.

Throughout school, I was like a Teenage Life Ninja, setting benchmarks for myself and reaching them with elite-level precision. I thrived on overachievement—something characteristic of many women in my generation, where every door seemed open to us. When I finally looked up at the end of high school, I was studious and well-respected by my peers and teachers… but not exactly “hot stuff.” I hadn’t forgotten Tom and Meg and love and witty romance. It had just fallen off the radar for a while. I’d built key life skills. I had great friends and a great résumé. But I hadn’t let myself get lost in a crush, stumbled through an awkward date, or even had my heart broken yet. As some of my friends flirted with guys and I remained completely inept, I was alarmed by the possibility that I was missing something formative—something our parents went through, and their parents before them—like dating, relationships, love. But that alarm was, like, tiny, because I had college plans. I just needed a romance plan, too.

I started editing my academic and athletic goals to include silent relationship ones—goals I’d figured out on my own, of course, because it was very uncool to admit you were clueless in the boy department. I spent months trying different approaches, yet my “plan” (pay attention; oscillate between receptive and aloof) wasn’t working. The Rules had lied. I was checking off personal goals left and right—a 4.0+ GPA, the National Honor Society, editor in chief of the school newspaper, all-state softball player and captain of the team, about to earn my acceptance to the University of Michigan (the only school I’d ever wanted to attend)—but I couldn’t seem to make any headway in the relationship department.

On the cusp of college, I finally just decided to make like Elizabeth Bennet and be as badass as possible until Mr. Darcy showed up. I had to admit: Lifelong, I could count my crushes on one hand. And most of them turned out to be lackluster, the more I got to know them. But I kept love as a goal. I did want to meet someone, someday. Maybe I was just too mature, I thought, and it would all even out eventually. Little did I know, my journey toward the book you hold was about to get a key flourish.

In 2009, I was leafing through an issue of Harper’s Bazaar when I started to read a profile about a Hollywood producer. SUSAN DOWNEY: IRON WOMAN was the headline of the story, written by journalist Kimberly Cutter.¹ I had never heard of Susan Downey but was vaguely familiar with her husband, Robert Downey Jr., who was rising to success (again) as superhero Iron Man and legendary detective Sherlock Holmes.

Susan, Cutter writes, was known around Hollywood circles as the “miracle” that saved her husband’s career. She was a young producer, an overachiever, a “straight arrow.” He was a talented but struggling actor who had bounced from substance abuse to jail to rehab in a series of bizarre incidents that left his reputation in question. They met on the set of the film Gothika, which she produced and he starred in.

Several things stood out to me. Susan was smart, and had been incredibly successful on her own before ever meeting her now-husband. Robert was a risk, so far from the Prince Charming prototype that was the stuff of my early imagination. And yet there was something about him that just clicked for her. “More than anything, I never doubted it,” she told Cutter. “There was something in my gut that knew really quickly. I knew three months in that this was it.”

The director of Sherlock Holmes, Guy Ritchie, told Bazaar that the pair represented “the greatest illustration of a symbiotic marriage that I’ve ever seen.” Susan tried to explain the connection, too. “There was something magical there, something we couldn’t put our finger on,” she said. “He always says that we became this third thing when we got together—something that neither of us could have become by ourselves—and I think that’s true.”

Susan was sure of herself, and thus, sure of her connection with Robert. “I don’t have a history of making bad choices,” she said. “And if my parents had any reservations—whether they were scared about [his being] an actor or an addict or that he’d gone to prison or had a kid and an ex-wife, the whole shebang of things I claimed I would never want in a guy, and add some new things to it—they never shared them with me. They saw how happy I was.”

Reading that profile was probably the first moment I became aware that there was another type of relationship—one that surpassed simple support, love, and admiration of each other. It was whatever Robert and Susan had—“this third thing,” a relationship that makes you better and encompasses both your personal goals and professional aspirations. A relationship that helps you grow.

I came away with two realizations: (1) If I didn’t combine with someone to become a greater “third thing,” in my own mind I would be settling; (2) I wanted to feel my romantic decisions deep down in my core.

Perhaps that’s why no relationships had ever panned out for me early in life. I was sure, at that point, that no one had ever ignited such feelings in me—and I was sure that I wasn’t the only one with this frustration.

By college, I’d catapulted out of my small hometown and entered a city alive with ambitious, bright young men and women. I felt at home, with my life and with love. I discovered more people who were chasing the sort of relationship ideal I was now seeking—one that felt truly worth it and bettering—yet I felt romantic angst around every corner.

In just a few short years, I’d gotten a full education in “modern dating”—and it was completely removed from what I’d ever imagined it would be. Apps were starting to become pervasive, online dating was a legitimate way to meet a significant other, and the age of marriage was inching toward 30 for college-educated career men and women. Suddenly, I seemed to have plenty of time to figure it out and tons of new ways to tiptoe into the game.

I was sort of an outsider in college: I lived off-campus and was freelancing full-time hours in addition to my full course load. I had my eye on a career in journalism, and my drive to achieve hadn’t let up once I entered higher education. And my closest friend was six years my senior, and I hung out with her circle frequently. But I also had a slew of friends my own age and was engaging in a lot of girl talk. I was learning more than ever from everyone’s collective dating trials. I approached the scene like a good reporter—listening, taking notes, investigating, drawing conclusions—all in the name of finally getting a handle on this love thing for myself. I chewed on some newly formed theories:

The media seemed to echo that brains over beauty was the new, highest relationship ideal—but it didn’t feel that way in real life. Most of the brainy ladies I knew were always single, or mired in drama with guys who didn’t treat them like this prototypical “ideal.”

There were gaps. Lots of gaps.

So I processed all of this in my subconscious, for years, learning and filing away information. I was also dating here and there, and noticed a fascinating trend: Guys were either endeavoring to wife me up or did not seem interested at all—at least not in the way I’d hoped. The middle ground was completely lacking, or befuddling. Yet in my early 20s, this middle “building” ground was exactly where I wanted to be. I’d found yet another gap.

So, again, like the journalist I was training to be, I turned to research. I started to notice studies and experts who spoke to some of the baffling dating phenomena surrounding me. I needed help closing the gaps. Then, finally, in 2015, a couple of illuminating studies hit my radar—research that helped me begin to connect the dots of our culture’s underlying relationship crisis: In a world where we have every possible option in life and love, why is it still insanely hard to land just one that lasts—the right one at the right time?

Dating isn’t dead but, rather, evolving in weird, unexpected ways.

Beginning in my 20s, I went on a lot of first dates with guys—actual honest-to-goodness dinner dates, where we sat in a restaurant and attempted to make small talk for two hours—but I felt next to nothing. I thanked them for taking me out and told them I had an early morning. Then I went home and ate ice cream, watching Real Housewives until my brain had melted, like the remnants of Moose Tracks at the bottom of my bowl.

Sometimes, guys were just not that into me (crazy, I know). I met guys who had totally different interests and guys whose personalities or life philosophies were awkwardly at odds with my own. All in all, there wasn’t much chemistry for me with a large subset of men—but my problem wasn’t that I didn’t connect with guys. Like most women, I did connect with a smaller subset of men.

I didn’t have a type, per se. Some were entrepreneurs; others, doctors. Still others were academics, and a few were business types. The one thing they all had in common was passion. Whatever it was they were pursuing, whether a PhD or a seedling of a business idea, they were committed—to change, self-improvement, growth, goals. These guys were almost always getting their lives in order—doing a residency; working insane hours; contemplating a move; choosing a grad school; building businesses—to the point where I never blamed them for being a little scattered. (My mom always told me that “men don’t multitask well.”) However, they weren’t just scattered. They seemed to defy all that old relationship wisdom proclaiming a man always knows what woman he wants—and will go after her.

They regularly ghosted and came back (hey, zombie!), which annoyed me to no end. They also often applied the brakes on even nonrelationships really quickly—sometimes before things had even approached lift-off, sometimes after one date—which seemed awfully premature. I began to label them as “skittish,” something women began to applaud me for. “OMG, yes! That’s the word!” my friends would say.

I wasn’t always going on real dates with these guys either. Romance was suddenly this charged, nebulous entity, which didn’t always include explicit declarations of interest. It was felt. It was frustrating. It was noticed by others.

One guy in my circle is a prime example. I had been tangoing around actually dating him for months. Since he wasn’t making a legit move, I had resorted to only acknowledging him in passing and simply letting it go. I was kind and interested in his life, but the buck stopped there. If he didn’t text, he wasn’t interested… right? If he didn’t ask me out, he didn’t like me… right? I’d given him lots of chances. So when a friend expressed interest in the same guy, I gave her the okay to go for him. Then, one fine day after a party where Tango Guy and I had inadvertently talked for most of the night, my friend called me up to apologize for ever making a move. “There’s obviously a connection between you two,” she said. “I realized the other night he doesn’t look at me the way he looks at you.” Huh.

I’d always assumed that when you felt a connection, you put yourself out there and you went for it. When you got a phone number, you used it. Those digits were pure gold! But the modern relationship equation is more complicated and layered; amid the sea of endless options, sometimes connection isn’t acted upon right away. Or at all.

Today, we often can’t define why a guy is a prospect, but we usually know if he is. I’d coined the term “The Look” for when it would hit me—that starry-eyed stare that would wash across his face at some spontaneous moment in the getting-to-know-you phase. If this moved out of nebulous-romantic-thing territory and into a relationship, you already knew there was an established connection and mutual regard for each other. It would probably take a leap of real commitment in the relationship wasteland among college-educated career folks—stepping up, knowing the stakes—more serious than a campus hookup.

However, to men, especially, it seemed, serious was scary.

I attempted to be superchill as I began dating my first real boyfriend; he wasn’t my type, per se, but his brain absolutely fascinated me and I had fun going on dates with him. He is still one of the smartest people I’ve ever met, and at the time we started dating, he was also rising professionally. He’d founded two burgeoning start-ups, and he was constantly busy, but he also walked me through the paces of early dating; he knew all the right moves and had high EQ (the product of two psychologist parents). But roughly six weeks into dating, after spending the vast majority of his birthday weekend together, we both felt the whoa-this-is-serious shift. Except while I was finally easing into a relationship based on real connection for the first time, he just panicked. He broke up with me, then reconciled just one day later. “I think I’m falling in love with you, and it’s scary,” he told me. We were up and down, on and off, for the rest of our short relationship, which never felt truly safe again.

When that relationship had run its course, the parade of skittish guys continued.

I went on three dates in five days with a guy who then suddenly disappeared. I awkwardly ran into him at a coffee shop when I’d assumed he was ghosting me, which led to a two-hour heart-to-heart about whether or not he could “do commitment” at that moment. He’d apparently promised himself he’d stay single after his most recent breakup. He hadn’t expected to meet me, he said; I hadn’t expected him to commit to me after one week of dating.

I connected with another guy on a dating app. We liked offbeat discussion topics and enjoyed a similar strand of quirky banter; communication was nonstop before and after a spontaneous 90-minute coffee date, where I’d showed up low-key (in workout clothes). I could tell he was excited to spend time with me, or even talk to me; his nerves gave him away. I thought it was sweet… before I got this text: Sincerely, I like you. I liked hanging out with you. You’re funny and interesting and exquisite. I like talking to you most importantly, but I’m not convinced I’m very good for you.

My girlfriends all died. “What?! What does that mean?” they said.

I then recounted the story to one of my best guy friends—perhaps to ease my developing complex. He laughed and said, “So basically, he thinks you’re amazing but just wants to sleep with other girls right now.” While I thought that was an appropriate surface-level reasoning, those endearing first-date nerves spoke to a more complicated internal framework.

I have endless examples of this skittish guy behavior on file in my brain—and in my journal, because I started to write them all down. A pattern was emerging in the group of guys with whom I felt the greatest connection: When the feelings hit, it was time to flee.

And it didn’t help that I’d grown up on He’s Just Not That Into You and The Rules, which taught me to make men work for it. They weren’t working for it—and I didn’t even get a say in the matter. The men I connected with were not the casual, free-flowing let’s-take-it-one-day-at-a-time creatures I’d been promised. Just because they were dating did not mean they were actually open to a relationship of substance, a relationship with potential for real heartbreak and hurt (and capital L Love). So if the men in the dating pool aren’t even open to Love, how do I find it?

If you’ve ever wondered that very same thing, don’t worry. I’ve got some ideas.

It’s been a lifelong process, an emotional roller coaster to bring this book to fruition. I’ve lived and breathed this journey—literally, metaphorically. I’ve woken up in the middle of the night on multiple occasions with ideas so major that I wanted to start working at 3:00 a.m. I’ve analyzed the research. I’ve talked to some of the best experts and major relationship influencers working today. I’ve had the pleasure of talking to more than 100 career-focused men and women of all backgrounds and ages, in depth, about their love lives—people from New York to LA; Chicago to Charlotte; DC to San Fran; expats from Indonesia to the UK. The ideas, echoes, and stories I heard were a dash of everything: chaotic, frustrating, brilliant, lovely, dramatic, sweet, sure, epic, thrilling, steady, erratic, very wrong—and, yes, sometimes, oh so right. The revelations were thoroughly modern and, I think, hopeful.

Researching and writing this book was life-changing for me; I learned more about love in one year than I had in the previous two decades. I hope that from reading it you get a sliver of the satisfaction and understanding that I’ve gotten from writing it. I want you to know: It’s out there. The exact love that you want is out there. But it takes patience, growth, tenacity, investment, discernment, a dash of timing, and just the right chemistry.

I know you want that lasting love—“it,” capital L Love, The One, your soul mate. But don’t rush; enjoy the ride. The ups and downs of this journey will only make the final destination that much more meaningful. Your love story is already in the making, set to intertwine with someone else’s.

It’s not easy. But it’s worth it. All of it. I promise. And it starts now.