Pride And Prejudice A few weeks later, a “Save the Date” from a couple I helped match reminded me why I needed to remain focused on the end goal, even if some of my clients were taking more roundabout ways to get there. Getting invited to clients’ weddings was a relatively new phenomenon. Out of respect for couples’ privacy— particularly the more high-profile ones—I usually took a back seat after an introduction was made. But after several engagements and weddings took place without including me, I began to question if a more passive approach was best. I wanted to see the manifestations of my labor! After years of missing out on this pleasure, I suggested to Lauren that maybe we could start triple-dating with some of our clients in an effort to get to know them as “units” rather than the individuals who initially signed up with us. The meetups that followed were fun, refreshing, and informative. We heard personal stories from them, witnessed looks of true love, and our very presence even nudged certain clients who weren’t yet engaged to each other in that direction. By remaining in touch, we were also granted front-row seats to baby showers and other momentous life occasions. “Shouldn’t they be the ones taking you out?” my mother asked me one day. “To thank you?” She had a point, but I’m not one to sit around and wait for something I desire. Something else I desired was to help form even more couples this year than I had in previous ones, and we were on track to do that—especially with the end of summer approaching. Singles who spent the last couple months living it up on vacation would typically return home to familiar feelings of loneliness that usually last through “cuffing season”—the colder time of year when daters are more likely to pair up. (A similar shift occurred following the COVID-19 lockdowns, which had made some otherwise ind ependent singles realize how much they valued having a strong and supportive partner to share their emotional and physical space with. The opposite happened too. Nobody wanted to be “stuck” inside with the wrong person.) Around this time, Kent reemerged to share that he was finally open to meeting Natasha, a bachelorette he’d passed on before due to her height. “I’m 5'8" in heels,” he’d written to me earnestly, “so I hope you’ll make sure that Natasha’s not just ‘okay’ with short kings, but seriously totes rad about this... Not looking for a woman who is walking in the door making concessions.” But after a month or so with uninspiring prospects, he reconsidered, and his feedback following their date was encouraging. “This was the most fun, comfortable, and friendly matchup so far,” he’d praised me. “Tasha (that’s what I’m calling her now) opened by saying something to the effect of, ‘I already feel like we’re gonna get along,’ which could’ve meant that she immediately put me in the dastardly friend zone, or the emotional connection was so obvious and authentic that we were meant to meet. Because we had our hands on each other throughout the evening, and because we’ve texted numerous times since, I’m guessing it’s the latter, but women are crazy. Let me know what she says. I had a great time.” Natasha, too, dropped me a line that she was excited about meeting Kent. More good news followed. A small handful of our couples became official in July, and Anna, the woman who had referred Callie to us, sent along an update that her boyfriend, Marc, recently introduced her to his family. And even Meera, to my shock, was still dating the dark horse, Trevor. I was really curious to hear more about their relationship in our upcoming session. The only major disappointment that summer seemed to be Callie.
Despite her lofty goal of meeting her partner within the year, she hadn’t allowed me to set her up once. The string of rejections had started with Jake, the bachelor I’d keenly described to her early on. She’d asked around about him based on the general description I gave, and discovered that her friend went out with him months prior—apparently an immediate disqualifier. She also shared she couldn’t date anyone sober, which Jake was. This wasn’t something we’d uncovered during our initial session together, so I tried not to read into it much. But she continued to reject others. “I reread the details, and I’m wondering if it’s Michael Smith?” she wrote to me about another bachelor’s description. “If so, his hairline kind of gives me the ick.” (I eventually learned she’d been Google-searching people using their phone numbers, so I learned ways to circumvent that.) When it came to Tom, she nixed him over the description of his salt-and-p epper hair, which she insisted was a “genetic” flaw not to be passed on to her children. She’d alerted me she could be “picky” when we met, but I’d taken the warning with a grain of salt (-and-p epper hair)—after all, everyone should be discerning about whom they’re going to spend the rest of their lives with. To me that isn’t picky, it’s smart. If a client brings a particular quality or trait to the table and expects the same of their partner, I’m always supportive of that request. For example, if a woman is really successful, she might want to hold out for a man as accomplished as she is. Or, if a man is in the top one percent of Bumble profiles, he might insist on only dating women with modelesque features. I don’t believe couples need to be equals in every category, though— I’ve seen plenty of blissfully happy couples who balance each other out in different ways—but I’ll never fault someone for trying to find that. Singles I actually consider “picky” typically fall into one of two categories: insecure or delusional. When someone’s insecure, they often worry too much about how others might perceive their partner, which can compromise the integrity of what they’re searching for. For example, a former client of mine had remained in an emotionally abusive relationship because, to the outside world, her boyfriend appeared to be a “catch.” Others might select a partner who will make them feel better about their own physical or emotional hang-ups. For instance, when a woman of size tells herself that only taller or broader men can make her feel safe and secure, that’s because she needs someone by her side who will make her feel smaller and more beautiful. Similarly, if a man insists on finding someone significantly younger, he might be trying to forget his own insecurities surrounding aging. Wanting a partner who has qualities others envy is understandable, but only when those qualities are in support of what brings you joy. Delusional daters, on the other hand, aren’t looking for a partner on their level. They’re looking to date “up,” without realizing they’re doing so. This inflated sense of self often manifests as an unrealistic view of whom they can attract. (How many people do we know who had one drunken make-out session in college with someone “out of their league,” and now believe anyone less traditionally attractive is “beneath” them?) Attempting to “level up” through dating isn’t new—Gen Z even has a term for it, “throning”—but this is usually a deliberate act driven by self-awareness. I want nothing more than for a client to be enthusiastic about someone I introduce them to, but if they aren’t embodying the type of match they want to attract, there can be a fine line between handing someone their “dream” person and setting them up for failure. Then again, sometimes that’s necessary. As Maria Avgitidis wrote in her book, Ask a Matchmaker, it can be useful for a client’s journey to “balance [their] wish list with a reality check.” I once had a client talk a big game, but when I finally put a woman he deemed “hot” in front of him, he had trouble making eye contact with her and talked her ear off the whole time about creative ways to earn airline miles. Her dismissal was humbling for him, and provided me with an opening to talk about which
women were actively looking for him back. Those women weren’t “worse,” I explained. They were actually better suited for him, and it takes a confident person to recognize the value in that. Once he began seeing himself through the eyes of his future partner, rather than women who weren’t interested in dating him, and viewing that as their loss, he was able to date more intentionally, and experienced stronger connections as a result. Callie didn’t seem insecure or delusional to me, but some of the reasons she’d ruled out matches had nothing to do with whether they’d be compatible with her—some were even issues with solutions as simple as a new haircut. So, what was holding her back? She’d also been traveling on and off ever since our initial session—for work mostly, but still a hindrance. While I’m all for clients living their best life, traveling that often is a common momentum killer in the beginning stages of any relationship—or, in Callie’s case, a roadblock to starting one altogether. I really wanted to help her, but it was becoming clear that she was getting in her own way. And, as we both knew, time was of the essence. It was starting to look less and less likely that I’d be getting a wedding invitation from Callie anytime soon. I wondered whether I would ever get an invitation like that from Meera. I certainly hoped so, but at the pace she was going, I figured it might be a long time in the making. Despite their passionate start, Trevor hadn’t said “I love you” since their second date, and he’d scaled back to seeing Meera only once a week (albeit for a consecutive two-day stretch over the weekend; these overnight visits almost always included some form of intimacy, but communication between dates was sparse). As my Zoom with her started, I adjusted my settings so she could screen-share photos of them together. A striking six-foot-three with blue eyes and a full head of blonde hair, Trevor looked, I had to admit, every bit the part of Meera’s ideal “Prince Charming.” Their infrequent but intense encounters also seemed to be well documented, ranging from their selfies taken at Temescal Canyon to what appeared to be Trevor’s kitchen. “These are great,” I told her, meaning it. “Have either of you posted these on your socials yet?” “We’re both pretty private,” she r eplied emphatically, though I could sense the disappointment in her response. I’m not one to push social media, but knew nothing would have given Meera greater pleasure than the chance to publicly show off her newfound love interest. She seemed to still be taking Trevor’s lead on pace, which wasn’t surprising given her dating history. For four years, she’d been in a relationship with someone who didn’t make her feel desired. Their sex life was minimal, and it had taken a toll on her. I could see that Trevor was making her feel desired and happy now, and to her, that felt like progress. “I just want to make sure he’s not hiding you,” I told her, my protective instincts kicking in. “It’s still early, but we said we’d revisit the exclusivity conversation after two months. How are you feeling about that now?” She looked baffled by the very question we’d spent the entire previous session deliberating. “Who cares?” She scowled dismissively. “Well, you did,” I reminded her. I wanted her to recognize how Trevor’s words weren’t exactly aligning with his actions—less to prove I was right, and more so to better pr epare her for a possible negative outcome. (In most areas of my life, I enjoy being right, but in my line of work, that often means heartbreak for someone I care about.) “Do you think I should bring it up to him?” She frowned. “I know he’s not seeing anyone else.” A series of cynical thoughts flashed through my mind: If Trevor isn’t seeing Meera during the week, and his communication is poor in between their dates, he certainly has time to date other women. And if this is happening, has he told them he loves them too? Or is he only seeing Meera, but made false promises earlier in one short-lived
moment of intensity? The continued absence of stated exclusivity worked in her favor. It meant I still had some wiggle room to convince her to see other people—and in the meantime, I could continue working on building up her confidence. She’d grown in that area since we first started working together, but I wanted her to get to the place where she wasn’t afraid to voice her desires in a relationship, knowing that doing so would attract the right man rather than scare him away. In addition, she was also on a journey in terms of how she viewed her body. Meera was a healthy weight, with some natural curves that she was constantly and unfairly comparing to the influencers populating her social media feed. I knew that embracing the body she was in would only increase her chances of finding everlasting love, because by loving herself, she would set her own bar for how she wanted to be treated. I’d instructed her to look at herself on her Zoom screen during an earlier session. “This is who your future husband can’t wait to meet,” I reassured her. “I want you to look at her, and tell me everything you love most about what you see. What are her best qualities?” Meera had thought about it, then listed her smarts, resilience, easygoing nature, and kindness. I’d waited for more attributes to follow, but they never came. “I love all that, Meera,” I remember sharing patiently. “But you can’t see any of that in your reflection. What do you see?” It’s not that I want clients to be superficial, but I wouldn’t be doing my job if I pretended that physical chemistry, and carrying yourself with confidence, didn’t matter. “Are you not seeing your beautiful brown eyes?” The corners of Meera’s lips turned up slightly. “Come on, I know there’s more.” After some pushing, I’d discovered that Meera also loved her smile, as well as her legs. She’d acknowledged that she displayed noticeably more confidence when they were accentuated. As a small tip, I’d advised her to start showing up fashionably late to dates, so that this asset of hers wouldn’t be hidden under a table when first meeting someone. She mentioned she’d worn a cute tee with high-waisted leggings for her first date with Trevor, which was a victory considering where we’d started. She had a long ways to go in terms of confidence, but there was only so much I could touch on. Attempting to offer guidance in areas outside my jurisdiction is a gray area, which is why I encourage many clients to supplement their journey to find outer love by using a therapist to help make progress with their inner love. But sometimes, it’s a tough line to straddle. Over the years, I’ve had to develop a sense for when things are moving outside my usual territory. I ultimately concluded that if I can stick to the present in conversations, I’m equipped to handle them. (“I feel like my insecurities make me a bad flirt. Can you give me some pointers?” Yes. Versus: “I feel like my insecurities stem from a childhood wrought with physical and emotional abuse. Can you give me some pointers?” Probably, but better to run it through a therapist first.) On the flip side, multiple therapists have referred clients to me, and some of my favorite clients are actually therapists themselves. The overlap is blurry, but there will always be actionable st eps I can provide clients that don’t in volve delving into their childhood trauma. Eliminating sources of negativity is one. In Meera’s case, the devil on her shoulder took the form of social media. When she scrolled through posts showcasing others’ “perfect” bodies or partners, she felt as if she could never measure up. The relationship piece affected her most of all. Photos and videos of happy couples had reminded her that, like her old pal Sle eping Beauty, she was stuck in time, while the rest of the world seemed to be moving on without her. “Maybe some of your friends are in the wrong relationships, and you’re actually ‘ahead’ because you’re taking the time to find the right person,” I’d tried to reason with her. “Or, maybe life isn’t a race at all.” I’d also brought up the Marie Kondo method, suggesting it could be applied to her digital world (the practice in volves
removing anything in your life that doesn’t “spark joy”). She’d agreed, and started unfollowing Instagram feeds that had once triggered anxiety, paranoia, or sadness. I’d noticed a positive difference in her demeanor almost immediately. Modeling for others how you wish to be treated is also crucial. Praising and speaking positively to the people you love is not only a nice thing to do, but it also invites others to respond in kind. Meera might initially question a “you look great too” from a friend, but after hearing it enough times, she might start to believe it. The line of thinking is similar to what some call “Lucky Girl Syndrome”—the idea that if you r epeatedly declare how blessed you are, good fortune will follow. “Okay, so should I break up with him?” Meera finally blurted. I hesitated to answer. Trevor had more red flags than a Canadian embassy, but if Meera wasn’t able to identify them herself, she’d simply put up with more bad behavior in her next relationship. “Let’s save that question for our next session.” Our time was almost up, and I made a mental note to talk to Meera about types of flags in dating. If I could get her to start differentiating between them, maybe she’d feel comfortable waving the white one soon with Trevor.