The Leading Man While I’d been in a good headspace following my meeting with Callie, one phone call with my fertility doctor changed everything. As with our first round of IVF—and the devastation that followed—our doctor had no scientific explanation for the failure. “You just have to try again,” she’d told us calmly, as if the conc ept of implanting another possible life-form in my body was the same as trying a new Pilates class. I started to wonder whether my end goal of getting pregnant was even possible. I considered canceling my sessions for the day, but I knew that out of all my clients, Kent would be an enjoyable distraction. He hadn’t been connecting with any of the phenomenal women I’d introduced him to so far, which was frustrating, but my conversations with him after all the ill-fated dates were so entertaining that I almost didn’t mind. He even invested in a membership upgrade, which came with access to a wider pool of bachelorettes, including former clients and acquaintances who weren’t yet enrolled in the service. It also covered date coaching. He initially insisted coaching “wasn’t necessary,” but came around to the idea when his ego got the better of him (he had to know how a woman had perceived him, even if he wasn’t interested in dating her). This type of curiosity always amused me. If he wasn’t interested in her romantically, what did he care how she thought of him? Over time I stopped sharing specific feedback with clients. I’d been burned too many times by those who used my honesty as ammunition, such as when a rejected attorney angrily texted his match, perturbed she’d complained to me how often he brought up his ex. “You’re the one who asked about my dating history!” he vented. If a client’s behavior is consistent, though, and can’t be traced back to one individual, I feel comfortable intervening—especially when that behavior is preventing them from making a meaningful connection. (“You have a tendency to bring up your ex on dates, and it’s turning women off.”) I couldn’t tell how much value Kent was getting out of our sessions, since he usually did more talking than listening, but for whatever reason, he k ept coming back for more. I’d been working with him in this capacity for a few months now, and nearly had his “stats” memorized. Name? Kent M**** Your age? 58 Height? I’m 5'8" on dating apps Sexual orientation? Straight. Where do you live, and what is your living situation? Own my house in Eagle Rock, where I share custody of my 2 kids every other weekend. Where are you from, and where else have you lived? Born in NJ but raised in NC, lived in the South for a bit before moving to CA. What’s your profession? Film director, investor, and vineyard and winery owner. Race or ethnicity? Nothing exciting. Religion? Jew-ish. Your political views? Middle of the road. Socially progressive. Would probably vote for any minority at this point just to move the dial.
How important is it for you to marry someone of the same faith? Would make my mom happy, but she’s been dead a long time. What is your highest level of education? Bachelor’s. Most serious relationship and when/why did it end? Does anyone really know? Do you want and/or already have kids? Happy with the 2, but with the right woman, who knows? Please describe your type, if you have one: Self-assured, ind ependent, early riser, positive. Someone with a sparkle in her eyes. Should look decent in a bikini. Do you have any dealbreakers? Jealous types, gold-diggers. Please list your hobbies: Biking, hiking, nature, horseback riding, time with my kids, I also play piano and drums. Always looking to try something new. Tell me something about yourself not listed above. It’s okay to brag: As a director, I’ve won multiple awards. But I’m most proud of my wine label. Oh, and I don’t own a TV. Scrolling through his profile again, I smirked, recalling the clearly dated headshot he initially attached, as if knowing what he looked like a decade ago would somehow overshadow any impression I’d have of him now. I’m always puzzled by clients who feel the need to send unsolicited photos of themselves, given that my company, in part, is known for its blind dates. Besides, whatever filters they use on their online dating profiles are wasted on me. The instinct for someone to misr epresent or de-age themselves speaks volumes, and those who do it usually wind up being especially looks-driven in their search, expecting to punch well above their weight class. Kent was a bit of a “silver fox,” if you went by his matches’ feedback, but he did look his age and refused to entertain a woman in the same category. He claimed he wanted to settle down but treated matchmaking like ordering off a menu. He whined about not connecting emotionally with the bachelorettes he was meeting on his own, but rejected the smart and successful women I recommended who would address that very issue. Still, I felt invested. Despite some misogynistic humor, he could be extremely intelligent and charming. And while he wasn’t especially vocal about his romanticism, I was convinced his inner Romeo was in there, somewhere— otherwise, why would he bother taking the time to meet with me so regularly? In a way, his self-assuredness and personability reminded me of my husband, and perhaps that’s why I was so motivated to help him. But he didn’t make it easy. I almost always meet with clients in person or on Zoom, since so much can be gleaned from facial reactions and body language. But Kent had been in postproduction on his latest movie, and let me know he’d be phoning me from his office during his lunch break. I was eager to address the callous re caps he’d been sending me following his recent dates, which—while admittedly entertaining—failed to steer me in the direction of a more suitable match for him. Kent was surprised when I broached the subject, claiming his feedback had been “pretty clear” so far. I pulled up some examples, hoping that by r epeating his words to him, he’d realize the fri volousness of his superficial generalities. I started with his thoughts on a woman, Kate: “‘I found her cute and attractive. Almost an “8.” I did not, however, feel a distinguishable need for carnal knowledge.’” Kent chuckled amusedly. “See? You got where I was going there.” “Svetlana,” I powered through, determined to make my point. “‘Not sure I wanted to bang her. You should feel comfortable setting her up with others, though. She’s a cool chick.’” I waited for what I thought would be a semblance of acknowledgment. Instead, he seemed pleased by his “generous” description. I moved on to Astrid, whom he called a “9.” “You didn’t feel like ‘mauling her face,’ though, you said. You see what I’m
getting at?” There was silence on the other end of the line. “When we first met, we agreed that physical chemistry is important. Even necessary. But you’re giving me nothing else to go by,” I complained to him. “Did you find these women funny? Smart? Did you open up to any of them?” “Jaydi, Jaydi, Jaydi.” He laughed jovially, as if he were the one giving me a lesson on dating. “None of that matters if I’m not feeling attracted to them.” “Okay. But ‘8’s, ‘9’s... these are objectively beautiful women you’re meeting here.” Even as I said it, I winced. Assigning numbers to women based on their looks is a common practice, but one that I abhor. That said, I’d never ask Kent, or any other client, to adjust their language with me, because hearing their uncensored thoughts is usually the best way to gain insight into their mindset. Something about the numerical classification triggered me, though. And then I realized: it reminded me of the grading system for embryos. In what is also a subjective process, embryologists assign letters to embryos based on their potential for development. Without knowing what’s going on genetically, they go by how embryos look. What I’d learned, though, is that grades have little to do with the outcome of a transfer: embryos that appear inadequate often work without a hitch, and ones that look great in a lab often possess defects invisible to the naked eye—evidenced by the life-form my body just rejected. Similarly, when it comes to a person’s appearance, other qualities such as personality and energy can really shape how attractive they appear to a partner. Studies show that confident and outgoing women are generally perceived as more attractive than more muted versions of themselves. I wasn’t sure how much Kent factored this in, but he should’ve known better. After all, how many “10”s had he dated only to discover that he didn’t enjoy spending time with them? And conversely, how many incredible women had he connected with in person, whom he categorically might have rejected online? I asked aloud whether he was focusing on the right things. Kent insisted he wasn’t as “picky” as I thought, so I suggested we try narrowing down his preferences more in the looks d epartment. Was he more into sweet or sultry? He said he could go either way. When it came to height, he declared he was “pretty open” there too. I felt my eyebrows subtly rise. Pretty open was not how I’d define Kent, but I pressed on, inquiring about curvier body types. (When we first met, he shared that he typically dated more petite women.) “I’m a boob guy, but I have my limits,” he added. “Curvy how?” “I don’t know. Curvy but fit. Take Kate Upton, for instance.” I threw out the first name that came to mind. “Would you kick her out of your bed?” “Who’s Kate Upton?” “Okay,” I chortled, adjusting for our generation gap. “What about Kate Winslet?” “I doubt I’d kick any woman out of my bed,” he responded hastily. “The question is: would they make it there?” I stifled a smile. “Okay. So why didn’t these other women ‘make it there’?” At first he worried about the optics of “putting someone down,” but he got over that fast. “Since you asked, Jaydi, and I guess it’s helpful for you to know: Kate’s voice was distractingly high-pitched, Astrid wore too much makeup, and there’s no way Svetlana would feel comfortable at a black-tie affair, which I have to go to sometimes. You know, for work.” “So Astrid wore too much makeup, but Svetlana doesn’t wear enough?” I r epeated back to him, making sure I understood his distorted logic. “She’s not feminine enough for me. I prefer long hair and a natural essence. Kind of like Darla.” And there it was. A week had passed since I’d first introduced him to Darla, a curly-haired and dynamic makeup artist I’d started working with recently. His written feedback about her was actually the most positive yet, and I was excited to dive into their date. He’d decided to meet her over a happy hour, which wouldn’t have been my first choice (for a while now, I’d suspected he had been double-booking himself, as his dates were feeling rushed). But according to both parties, his date with Darla went well. I glanced at my notes, armed with Kent’s colorful description of the
evening. “Darla was great. We shared a talk-time ratio of 50:50, which was really nice. Talked about you and your business a little bit. All good. Question: she said that her friends are comprised of people who have ‘shared beliefs and shared experiences.’ I heavily gravitate toward people who have friends from all walks of life. Might be a mismatch for this reason. All said and done: very sweet and engaging person. I’d have made out with her, but not in the 5:30 p. m. stink of Hollywood.” Perhaps now he’d buy into my reasoning for scheduling dates later. Statistically, I always have more success when they’re scheduled after seven, and the data supports that. There’s an increased feeling of intimacy and romance at night, when there’s typically fewer distractions, and let’s face it—the lighting is better! Women r eport feeling more confident when blemishes and imperfections are masked by the moonlight, or the forgiving dim of a restaurant’s warm lighting, typically used at night to create the feeling of a more relaxed atmosphere. There’s also a hard out, if it’s needed, or a natural transition to a sle epover. I wondered whether he was planning to see her again, and he shocked me by nonchalantly revealing they’d already had two more dates since the first. I couldn’t believe it. “You buried the lede, Kent!” I grinned, intrigued. “You must really like her.” “Nah,” he said, somewhat dismissively. “My ex just had the kids for the weekend. Darla’s great, but I don’t think we have enough to talk about.” As he explained that he didn’t plan to see her again, I wondered how to pivot. Kent often tried to elicit reactions from me, and I wondered whether that was happening again here. If I pushed him to continue seeing her, he’d likely resist. But if I glossed over his blatant dismissal of her, he’d probably see through it. Instead, I decided to capitalize on his good spirits and ask if he’d be open to some “wildcard” introductions. I’d given him the “best” of what he’d asked for, and now I wanted to try things my way, like having him meet someone closer in age. Normally I had to be careful with clients when broaching the idea of expanding previously agreed-upon search parameters. Often, the suggestion of doing this triggers feelings of insecurity or failure. Many people don’t believe they deserve what they’re asking for in the first place, so the moment you challenge them to consider alternate options, they worry that you don’t believe their asks are attainable either. I would never want a client to lower their standards, though. Instead, I liken the conc ept to ordering fish at a restaurant. The majority of people request popular fish, such as salmon or cod, which are lower in mercury, and typically reside closer to the ocean’s surface: fewer explore the bottom-feeders with migrating eyes and inferior mouths. But sometimes, those are the tastiest! And by trusting, let’s say, a seasoned sushi chef (or matchmaker), that omakase experience might introduce you to a fish you’d never have tried, but that you’ll be salivating over thereafter. If only I could get that through to Kent. “Don’t worry,” I assured him. “I know your taste.” “Okay,” he offered finally. “But if she ain’t sushi-grade, I’m sending her back to the kitchen.”