Introduction As a six-year-old kid in South Florida, watching Billy Crystal belt clever musical parodies onstage way past my bedtime, I dreamed of winning an Oscar one day. (That vision stuck: my bat mitzvah theme was “the Academy Awards.”) But even as I continued to fine-tune my acc eptance speech, I never imagined I’d be matchmaking some of the nominees one day instead. Working in the entertainment industry for several decades, I became a fly on some pretty glitzy walls. Whether I was a guest on an A-lister’s private jet or watching forbidden bonds form on rainy-day movie sets, I learned that the people I admired most in life were exactly that: people—and this meant that most of them, like the rest of us, struggled with their dating lives. And no matter how many blockbuster films or accolades they’d accumulate, it seemed that in the absence of romantic love, they concluded that their lives were devoid of meaning and purpose. I didn’t notice this initially, because I was too busy attending networking events or attempting to prove my chops in a male-dominated, cutthroat environment that required the majority of my attention. But as I accumulated TV credits, and survived some pretty toxic writers’ rooms, my professional dissatisfaction started cre eping in. At the encouragement of friends, I started a matchmaking “side hustle,” born from my natural instincts to help connect people—and the parallels between it and my day job quickly became apparent. To craft compelling characters as a writer, I had to dig de ep to figure out what made them tick. The same held true for matchmaking, exc ept in that case, I was dealing with real people. I soon realized that introducing one happy couple would bring me ten times more joy than penning the 250 th episode of Family Guy ever would (and I admit, that brought me a lot of joy). That’s not to say I’m not proud of my writing accomplishments, but when I think about how I want to be remembered one day, it’s not for penning fart jokes for Liam Neeson: it’s for helping people find their forever partners, the ones they’re comfortable farting in front of. I’m not the first matchmaker in Hollywood. (A mutual friend supposedly set up Prince Harry and Meghan Markle on a blind date, and Ed Sheeran introduced Courteney Cox to her musician partner, Johnny Mc Daid.) I’m just one of the first to do it professionally. Over the years, my clientele has ranged from high-powered studio execs and actors to Emmy Award–winning writers, former child stars, and even celebrity body doubles. But I’ve always been a firm believer that love should be accessible to everyone, and my diverse database reflects that. In this book, I share insight into three clients’ journeys with me—each a composite of several I’ve worked with over the years. I’ve also changed various names throughout to protect confidentiality. Choosing whom to highlight was difficult, because to some degree, I’m invested in every client I work with. My excitement is palpable when they have a mind-blowing first date, and so is the pit in my stomach if they get their heart broken. But I must admit, I connect with some more than others. (Any coach who claims complete objectivity is, at best, fooling themselves.) In my case, I’m most drawn to people who share my same driving force in life—for some that might be success; for others it’s fame; and for still more, it’s having a good time. But for those who’ve jumped for joy in college dormitory stairwells following an intense first make-out session, or sobbed hysterically singing along to Keane’s “Somewhere Only We Know,” our driving force is love. Whether you’re the hopeless romantic, the one in a rush to “make it happen,” the one who’s convinced yourself you’d be better off alone, or even the one who’s “figured it all out” but wants to play matchmaker for your friends, my hope is that you’ll recognize yourself in these stories. If you’re lucky enough to have already found your forever partner,
you’ll relate to the journey of my clients and instantly be transported to the time in your life you feared you might wind up alone. And if you’re in that headspace now, you’ll learn more about who you are, how you fit into the dating lands cape, and what more you can do to achieve your desired result. Like in some of the best movies, a spoonful of sugar helps the medicine go down. (The sugar in this case is the journey of me and my clients, and the medicine is the actionable tips and tricks you’ll realize are suddenly in your arsenal—the effect of ten one-on-one coaching sessions with me—by the time you’re done reading this book.) I also use these characters as vehicles to address common dating dilemmas everyone can learn from. Given my background, I’m savvy about the mixed messaging pervasive in the dating industry—one I was also exposed to before I met my husband. For instance, should you hold out for someone who checks all your boxes, or should you settle for someone else “good enough”? Should you bring up politics at the beginning of a date to help gauge someone’s values, or avoid the topic altogether? Should you sle ep with someone on night one, if you’re feeling it, or wait until you’re dating exclusively? I’m here to tell you, like with all your other burning questions, it d epends. I understand why witty catchphrases and universal rules and charts are appealing: it’s tempting to follow every get-love-quick method if you only complete st eps X, Y, and Z. But when it comes to dating, I’ve found that what works for one person might completely r epel another—and this nuanced philosophy is reflected in my coaching style, and in these pages. I also hope to foster empathy for “the other side,” or some of the “offenders” you’ve dated—the ghosters, the catfishers, the love bombers, and those darn singles who simply won’t commit. As someone who has coached many of those men and women, I shed light on why they might act the way they do. And if you’re guilty of some of these behaviors yourself, perhaps reading about the effect they have on hopeful singles you come across will cure you of these bad habits once and for all. In addition to sharing insights about various types of daters, I also analyze the rising popularity of matchmaking (in part due to popular films and dating app burnout). I not only illuminate the perks of investing in such a journey, but also expose some bad industry practices to help guide you toward selecting the perfect matchmaker or dating coach, if that’s what you’re in the market for. Some people believe that’s AI. Founders and CEOs of major tech companies have suggested that AI bots will be able to provide superior coaching one day, whether it’s for use within the unique ecosystem of their apps, or even lessons applicable to in-person dating. While I recognize the merit of AI’s in volvement in the dating sphere, I don’t think it—or even the world’s best human dating coach—can top your own experience, education, and intuition, should you choose to start relying on it. The best dating coach, in my opinion, isn’t someone you can turn to for advice, but someone who enables you to start trusting the advice you give yourself. This is a mindset I hope all my clients will eventually adopt, and one I hope to impart to you, as well. To trust the advice you’re about to receive, though, I’d also like you to get to know me. Some coaches make a point of not getting too personal with their clients, but I find that providing a glimpse into my own life, whether it’s a win in the present or a mistake from my past, helps to normalize a client’s experience and allows us to better connect—something I’d like to do with you. I’m eager for you to know more about me and my dating history, what inspired me to get into the matchmaking business (and eventually the date-coaching one), how I created my company, why I structure it the way I do, and how all this led me to the happy marriage I’m in today. Not everyone can get high on their own supply and marry their client (more on that later!), but if I can achieve my “Hollywood ending,” I know you can too—whether you’re an A-list celebrity or movie set extra.
Preface Squirming uncomfortably in my hospital bed, I looked around the room filled with several new faces and wondered whether they were judging me. When I had purchased my custom-made medical gown off Etsy, I’d thought the blue and white abstract pattern would help take my mind off my anxiety. I’d known today was coming for a while, and hoped to don something other than the ill-fitting, d epressingly bland covering standard for such experiences (clearly a common thought given an entire category on the shopping platform is dedicated to such garments). I’d even gone so far as to find out the specs of “normal” hospital gowns to ensure that my creative alternative would get approved by staff. But as I lay outstretched on the hospital bed like a chicken waiting to be spatchcocked, it occurred to me that my thoughtfully procured, stylish getup was doing very little to ease my growing discomfort. Several pairs of hands maneuvered around my body, tearing off elastic strips and pressure-sensitive gauges that had been monitoring my vitals, and I did my absolute best to disassociate. Dave will be back any minute to help calm me, I told myself. Or maybe he’ll miss this procedure entirely (although the nurses did claim it “couldn’t hurt” for him to visit the cafeteria—a place, I’m now learning, where all cell phone rec eption goes to die). Will I die today? The thought crossed my mind as the masked-up strangers started wheeling me out of the room. “He’ll be back soon. Don’t worry,” a nurse tried comforting me with an upbeat tone that felt strangely out of place given the urgency of the situation. I felt the medical team quicken their pace as they continued ushering me toward the operating room. I was feeling a little faintish, which the clairvoyant nurse seemed to clock. She attempted to distract me. “Is it true you’re a matchmaker?” I think she asked. (I say “I think” because I was so doped up on narcotics that I can’t be sure.) “Mm-hmm.” I nodded politely, scanning the hallway for my husband. “Wow, amazing,” she continued heedlessly. “So what’s, like, your craziest matchmaking story?” I shielded my eyes from the light as the double doors to the operating room swung open. “Anything you can share?” The last fifteen years of my professional life flashed before my eyes. Over time, I’d collected dozens of zany, ridiculous, hard-to-believe stories that I k ept at the ready for this exact kind of question, but as I braced for one of the scariest moments of my life, I didn’t find myself thinking about my most outlandish clients at all. Instead, I thought about some of my favorite ones—all of whom I’d worked with until not too long ago.
Act One
The Inciting Incident I wasn’t in a nineteenth-century shtetl, conspiring with a woman’s friends and family to arrange the perfect marriage for her, nor was I a third-generation matchmaker, born with the road map to love coursing through my veins. Rather, I was a self-trained dating expert, sitting in sweats in my home office, still trying to figure out the basic mechanics of Zoom. It was 2020, and I was about to meet my newest client, Callie, on the recently popularized platform. As I waited for her to appear on-screen, I admired my background, which didn’t always look so professional. The built-in bookshelf behind me displayed a wide array of relationship and self-help titles from gurus I admired (and loved to critique), along with an assortment of endearing trinkets my husband and I had accumulated over the years, including a framed Shakespearean quote, colorful Cuban cigar boxes, and a r eplica of a WWE wrestling belt—a remnant from Dave’s bachelor life I generously suggested we ke ep. The curated setting was appealing to prospective clients, but the truth is, I much prefer relaxing on my comfortable but awkwardly low custom couch in the corner of the room that sports a blank white wall behind it. As a writer, I never really feel creative or productive at a desk, and find that the same holds true as a dating coach. Clients also respond better when it feels like we’re just two friends gabbing away on a sofa. But Callie was a new client, and I wanted to impress her. I thought about hiding Dave’s wrestling belt for a moment, but decided to leave it be. It was usually a good conversation starter. When I noticed Callie’s name in the waiting room, I ran my fingers through my ponytail and plastered on a welcoming smile. I was in my usual getup: dressy on top, casual below, a virtual matchmaker’s equivalent of a mullet. I quickly shrank the Zoom screen to fit beside the profile I’d created for Callie, so I could seamlessly glance between the two. The standard information was hardly a comprehensive road map to what makes a person tick or what they’re looking for in a partner, but it allowed me to skip some of the basics during our conversation. Name? Caroline “Callie” R***** Your age? 42 Height? 5'4" Sexual orientation? Bisexual (though I’ve mostly dated men). Where do you live, and what is your living situation? I own a two-bedroom condo. Where are you from, and where else have you lived? Providence, Rhode Island. Philly for college. What’s your profession? TV studio exec. Race or ethnicity? White. Religion? None but I was raised Protestant. Your political views? Liberal. Trump is infuriating. How important is it for you to marry someone of the same faith? Not. Prefer someone spiritual over atheist though. What is your highest level of education? Undergrad at UPenn.
Most serious relationship and when/why did it end? My ex wasn’t ready for kids. Do you want and/or already have kids? I do, and froze my eggs a few years ago (thanks, WB insurance!). Please describe your type, if you have one: Smart, funny, slightly corporate, successful, loyal, likely still reads the newspaper. Into finance types. Someone who has a passion for what they do for a living, or even a hobby. I dated this guy once who was obsessed with a flight tracking app, and he was able to identify planes based on their silhouettes. That’s hot. Do you have any dealbreakers? No one unemployed or aspiring, bald, or short. Absolutely no one with birds, and definitely no exes (will share more in person)! Please list your hobbies: Playing violin, pickleball, skiing, going to concerts, traveling, listening to podcasts, brunch with friends. I’m also weirdly good at throwing axes. Tell me something about yourself not listed above. It’s okay to brag: I was in Forbes’s “30 Under 30.” I’m also a former high school sailing champion. “Hi!” Even over video, Callie was clearly stunning: sophisticated with stylish, short hair—how I would have pictured Audrey H epburn if she’d been in a rock band. There was a darkness to her energy, but she also exuded a calm confidence as she waited for me to speak. Small talk is usually my business partner Lauren’s thing (“small talk, big connections,” she liked to remind me), but she was currently on maternity leave. Without her, I could sometimes start off a bit awkwardly. (“Nice to meet you. I’d love to hear more about the cult you es caped as a child.”) This time, I stuck to her playbook and asked Callie how she knew Anna, an assistant director and former client we matched successfully, who referred Callie to our service. I always ask how close a connection is, in case there are any overlaps in possible matches. (I once played a role in two friends’ falling-out—all because I’d accidentally introduced them to the same man. Avoiding this requires some sleuthing, but hey, I don’t need any more blood on my hands!) Callie informed me she and Anna were merely work friends, and suggested they had different types anyway. “No offense to Marc,” she offered, referring to Anna’s boyfriend. I found talking to Callie to be easy. I learned that after graduating from UPenn, she’d moved to LA with the goal of working with actors. She started at an agency but quickly fell in love with TV development, and wound up acc epting a job at a major studio. The youngest executive in her d epartment, she dedicated the majority of her late twenties and thirties to her career, with pretty impressive results—some of my favorite shows in the last decade, it turned out, were ones she’d helped sh epherd to screen. She was happy, but one day she’d woken up and realized she was alone. Most of her friends were married with kids, and she found herself longing for permanent companionship. She’d thought that if she treated dating like a job, she’d eventually find that special someone, but after several dead-end courtships and some good laughs on Raya, she had grown dissatisfied with her prospects. And she was determined not to settle. Based on her questionnaire, I already had several men and women in mind for her, but first I had more to discuss, like what age range she was open to. We landed on 32–52, which gave me plenty to work with. “But let me ask you a question,” I threw out there. “If I meet someone fiftythree, who otherwise fits what you’re looking for, do you want me to categorically rule them out for you? Or would you want to at least grab a drink with them?” She r eplied that she’d want to grab a drink, so I pressed for her actual limit. I don’t do this to test people, but rather to ensure I’m not accidentally ruling out someone’s future husband or wife based on a birthday. Age ranges are useful on dating apps, when you know little else about a person and are conducting your own search. But the benefit of using a matchmaker is we can help flag any outliers for you. I rattled off a few other outstanding topics:
Was she down with someone who already had kids? Since she wasn’t politically active, was she open to someone else who might be? What about someone who does mushrooms twice a year in the desert? After Callie responded to everything with ease, I was feeling hopeful —no, excited. She seemed to know what she wanted, but was also open to someone else outside of that. “I feel really good about this.” Callie smiled effortlessly as I continued to pick her brain. “I looked into doing IVF, and I mean, I’ll go ahead with it if you can’t find my person, but it would be so much better to have a kid with someone else, don’t you think?” I wasn’t sure whether she was asking rhetorically, so I waited. “You can make that happen for me this year, can’t you, Jaydi?” she suggested, half jokingly. “You’re my last hope.” I froze, feeling both honored and horrified. For years, I strove to be a beacon of light for those struggling to date in a difficult lands cape—dating is tough anywhere, but in a city like LA where people are self-absorbed, pursuing their own passions, and constantly searching for the “next best thing,” knowing where to find a quality person looking for something real is tough—but never had I thought of myself as anyone’s “last hope.” “When you say ‘this year,’ do you mean by December?” I questioned, feeling panicked. “No, no,” Callie reassured me. “I mean the end of my year. With you.” The distinction wasn’t much better. A year is a good amount of time to find someone’s match, but the consequences were greater here if I failed to produce one. We weren’t talking a possible membership renewal, or another round of online dating, if the One failed to materialize. We were talking about Callie pursuing motherhood. On her own. I felt the knots tightening their grip on my stomach. I was already incentivized to find her someone great, but this added challenge felt like a veiled threat. The last thing I wanted was to compromise on quality for her as a result of added pressure or guilt. What’s more, Callie had no idea how personally her request weighed on me. Dave and I had been struggling to conceive for a while, and finally, after resorting to IVF ourselves—after what felt like endless needle pokes and procedures—I was technically seven days pregnant. (At least, I hoped I was. The more reliable blood test to confirm it all was in four days.) I’d tried imagining many times what my own journey to bear children would look like without Dave by my side, and every time, I’d come to the same conclusion: I wouldn’t want to do it alone. If Callie couldn’t find her partner in time, would I be partially responsible for her shouldering that burden? I took a de ep breath and reminded myself that I’d “solved” harder cases. Her declaration of intent had caught me off guard, but ultimately, I admired her resolve. (I actually know many people and former clients who’ve expanded their family through fertility assistance—at least four single women and one single man—but hadn’t been an instrumental part of their IVF journey since it took place before or after their memberships with me.) Callie was forty-two, and statistically, her window was closing to make her dream of having a biological child a reality. She was willing to do it alone if she had to, and it was my job to honor that possibility. What’s more, I liked her. Clients might benefit from their therapist maintaining a certain sense of detachment in order to remain as objective as possible, but my job was to be subjective: to use my experience and instincts to help make meaningful connections happen. It was only natural that the more I got to know a client, the more invested I’d become in their journey. And the more invested I was in their journey, the more motivated I’d be to hunt down every possible lead for them. Fortunately, Callie had also signed up for date coaching. The majority of my clients come to me wanting the “quick fix” solution of having their husband or wife handed to them on a silver platter. But this implies the table is already set. Callie seemed to have her act together, but experience told me there was more to her relationship status than a string of bad luck. Before diving in with her, I planned to conduct a routine
“health and wellness” check on her dating life to get a better handle on her history and confidence level. I also needed to dig de eper on what type of partnership she was seeking. Did she want something more traditional or modern? Did she envision herself with a spender or saver? The list went on. As I scheduled our next meeting, I could sense Callie’s renewed optimism. She was smart. She was successful. She was determined. And, in that moment, I decided I could help her.