Recovering From Heartbreak I’d been eagerly awaiting my final session of the day. Kent had k ept me hanging after our last meeting, and ever since, I’d been dying to know more about this supposed One Who Got Away. If he took up half our session talking about his winery again, I was going to start drinking. “Don’t worry your pretty little head,” he told me knowingly a minute or so in, “I’ll tell you about Kate.” I got out my metaphorical popcorn and strapped in. “She was perfect,” he started, more seriously than I was accustomed to. “But really perfect. Not the bullshit I spew after a first date with a woman who wore a tight skirt, which as you know does quite a number on me. So it won’t come as a surprise that I fucked it all up.” I waited patiently for more. Kent shared that they met when they were fifteen. Kate wore hand-me-downs from her sister and Coke-bottle glasses, but even with them on, he said, she was the most beautiful person he’d ever seen. Her dad gave him one of those “if you hurt my daughter” lectures later, but there was no point. “Only an idiot would hurt a girl like that,” he confessed. “So I didn’t. At least not right away. “We were ins eparable until eighteen, the summer before college. I was moving away, but told her I’d make it work. I would have driven hundreds of miles to see her back then.” He closed his eyes, losing himself in the memory. “But that summer, my brother, Garrett, died.” For a moment, my heart caught in my throat. I’d never heard Kent mention a brother before, but as he collected himself, I could tell the loss had been immeasurably profound for him. “Kate was away when it happened, on vacation with her family or something. And my parents...” He trailed off, unable to put the impact into words. “No one could believe it. He was an honors student, class president who played lacrosse—because it wasn’t enough to be smart and popular, right?” He allowed himself to chuckle. “He had to be athletic too. And it was all for nothing because he got into the wrong car at the wrong time.” He grimaced, and I was gutted for him. I had seen firsthand the lifelong scars this kind of loss can cause: my mom’s sister died when she was pregnant with me, and my grandparents and aunts haven’t been the same since. “I had a lot to drink at the funeral.” He powered through his story, and I understood. If he stopped, he’d probably shut down for good. “Kate was out of town, and that was who I really needed there. You know? But Garrett’s friend Sandy, she was destroyed too. Like, absolutely wrecked, and drinking like the rest of us. And before I knew it, one thing led to another and...” His voice trailed off. “Kate tried to forgive me. But things were never the same again. I mean, how could they be? Even buying a ring for her after didn’t change that.” I let out a small gasp. “You proposed to her?” Kent? The man who could never commit? “She said yes, if you can believe it, but that didn’t last long. Every fight, every argument... it just ended coming back around to what I did. And I deserved it too—her leaving me. She should be with a man who knows better than to ever fuck up something that good. I guess I’m just not capable of it.” “You were so young.” I felt for the distraught boy inside Kent he still hadn’t let go of. “You can’t beat yourself up for one mistake forever.” “Oh, honey. I don’t do that anymore. There is no undoing what I did.” He got curious years later and looked Kate up on social media. She was married, apparently, with three kids, and even one grandchild. If he’d ever fantasized about getting back together with her one day, that ship had long sailed. I agreed with him that you can’t undo the past, but added that he still had time to build a beautiful future, with someone new. “Every love is different. I can’t promise it
will be the same as your first one, but I can promise you’ll be glad that one ended. Because if it didn’t, you wouldn’t be able to feel the incredible love I know you’ll feel again one day, the kind you can only feel after going through such an excruciating kind of heartache, one that will make you never take your next love for granted.” “Do they make you pass some sort of corniness test in order to become a dating coach?” he asked me cheekily. I had known, even as I was speaking, that Kent would have some sort of response like that. Even when recalling the most traumatic parts of his life, he still managed to maintain his sense of humor. “I’m serious. You feel like you don’t deserve Kate, but that doesn’t mean you don’t deserve love.” “Maybe. Or maybe I’m just meant to have flings with women half my age for the rest of my life. Are you saying I don’t deserve to have fun?” “Is it fun for you still?” I asked him blankly, genuinely curious. “How old is Kate now anyway?” “She’s my age. We went to high school together. Jesus, weren’t you listening?” “I was asking rhetorically,” I told him slyly. “She’s your age, which is exactly my point. Maybe it’s time you start dating women your own age.” The Gardener had been a st ep in the right direction, but even she was a full decade younger. Kent grinned. “You’re good, Jaydi. But not that good.” Dammit, I thought. Even on a day when he was feeling this vulnerable, I couldn’t get him to reconsider. Why is it people complain about being single, but categorically rule out fantastic someones who could potentially cure their loneliness forever? The woman I’d been envisioning for him, Rita, would have to wait a little longer. Later that day, I got word from Callie that she wanted to meet, and I happened to have a cancellation. She seemed in good spirits, and I wondered what the urgency was. She shared she recently got a promotion at work (amazing!), but that she’d also decided to end things with Rachel (boo). And in true Callie fashion, our exchange about it all raised more questions than answers. “I realized I want to end up with a guy,” she shared as casually as she would about her favorite flavor of ice cream. I couldn’t help but feel amused. Dave’s earlier speculation had been wrong! I wasn’t sure removing all women from Callie’s dating pool was the answer, though, and worried that her breakup with the set designer was less about gender and more about her instinct to run away from someone once their connection grew de eper. Or maybe she was right to distance herself. We can’t always point to why someone isn’t right for us. Sometimes it’s only a feeling. Before processing hers, Callie asked if I had any men in mind for her, and I worried she was being pulled in two different directions, both stemming from fear—fear of not getting to have children and fear of settling. The push and pull seemed to be constant, and always landed her in the same place: alone. I wondered who she could be once the shackles of fear were removed, and hoped I’d be lucky enough to witness that transformation. But currently, Callie was having trouble seeing past the looming expiration date of her membership, and worried she was no “better off” than when she first signed up with me nearly a year ago. I worried her speculation discounted the growth I’d witnessed from her— growth that would help her better connect with the right partner. I also explained that she and I were operating under different timelines—mainly that she had one at all. That’s not to say I lack a sense of urgency on behalf of my clients, but I’m unwilling to compromise the integrity of my search for a mutually desired outcome. Callie had informed me from the outset about her plan to initiate IVF on her own if she wasn’t willingly paired up with a potential life partner soon, and I respected she was disciplined enough to enforce the self-imposed deadline (something I normally advocate for). But I sensed that in a rush to make her dreams happen, Callie was delaying them more. “What about a partial refund?” she asked, so innocently that it felt like a double gut punch. “I mean, for our remaining time together?”
I felt hurt and fury bubbling to the surface. The amount of behind-thescenes work I’d done for Callie this past year was tremendous—not to mention our coaching work together that would have long-term benefits beyond just her membership. And never mind that our delayed start was entirely a result of her own self-sabotaging. Besides—I felt myself getting fired up—I had just introduced her to someone she hit it off with for thousands less than what most matchmakers charge! “It’s fine if not,” Callie added uncomfortably, probably sensing my energy shift. “Just figured I could use all the funds possible if I’m going to end up going the IVF route.” I allowed myself to feel compassion, imagining her anxiety. The thing she wanted most in the world wasn’t coming to her as readily as she’d hoped, and that was scary. I thought about other times I’d been blamed for someone feeling down about their prospects. I’d been inculpated for not setting someone up often enough, because they interpreted the lack of introductions as me undervaluing them. “Am I not worthy enough for one of your bachelors?” they’ve wondered, when oftentimes it’s the complete opposite. I think so highly of them that I’d rather hold off for a stronger match than set them up for “the sake of it.” Frequency is not an indicator of value when it comes to matchmaking. Quality is. And frequency can backfire, especially if there’s a lack of chemistry present on the dates. “This is how you see me? You think that’s the best I can do?” is a phrase I prefer to avoid. Most notably, these frustrations are often expressed by our least confident clients. The others will usually brush off a “bad” date quickly, choosing to focus communication around how to improve the next one. Or they will check in if there’s a lull between matches, and feel reassured hearing that we’re holding out for someone we’re excited about. Rather than internalize the feedback, I do my best to empathize with how a client is feeling—how I used to feel when I was single too, wondering if I was going to be one of those unfortunate people who winds up dying alone. Callie was relatively confident, but her insecurity surrounding timeline was allowing fear to drive her decision-making. But I’m a fair person, and if I’d only set her up a few times by the end of her membership—even if part of that delay was of her own making—I’d be open to extending it for at least one more match. My investment in her also wouldn’t end once her membership expired. “Just because I won’t be your matchmaker at some point doesn’t mean I won’t still care. We both want the same outcome for you.” “Babies?” she asked me hopefully. “Your happiness.” Endings seemed to be the theme of the day. To my surprise, Meera broke things off with Trevor. This time for good. He’d canceled their weekend getaway to Northern California to meet her family, citing that he was “too busy with work” again—and something in her finally clicked. Instead of crying during our session that followed, she looked focused, as if sheer determination alone could get her to suddenly move past the relationship she’d been pouring her heart into over the last year. I was proud of her for ending it on her terms, since that was likely the only way the breakup was ever going to last. I’d seen far too many women and men in Meera’s position actually marry the very person causing them so much pain, and was relieved she had decided to forge a different path for her future. I knew how much she’d been wanting Trevor to meet her family, and for the relationship with him to work out in general. “Thanks for being there,” she told me grimly. “I’m not sure I could have gotten through this without you.” “You followed your heart,” I comforted her. “But maybe in the next relationship, we’ll have your head do a little more of the leading.” “Or maybe you can lead?” she joked, and suggested I set her up with someone else as a distraction. The benefit of waiting until you absolutely can’t take it anymore to end a relationship is that it’s possible to immediately feel ready to start another, a mindset I related to firsthand. I should have broken up with my ex years before I did, but the more friends and family tried convincing
me he was all kinds of wrong for me, the more I doubled down and defended him. Behind closed doors, he and I would have all-out nasty brawls that would leave us both in tears, and we’d regularly confuse passion for intimacy. But he was extraordinarily persuasive. Every time I worked up the courage to break up with him, he’d somehow manage to convince me it was the wrong decision—and that everything would be wonderful again, if only we could start over. And so we did. Finally, after three years of this insufferable dance, I successfully ended things over text. Worried he’d do what he always did, which was show up at my doorst ep to try to win me back, I decided the only practical solution was to leave Los Angeles. I packed an overnight bag, told my two closest friends, and drove north without a plan. I felt suffocated, and thought the only way I could breathe easier again was if I left the city entirely. The air would feel fresher somewhere else, I reasoned—somewhere else not poisoned by the negative energy of my ex. It was the closest I’d ever come to having a breakdown. An hour or so into my late-night drive, I woke up my mom in Florida to share she’d been right about him all along. Rather than relish being “right,” she did the most loving gesture possible in the moment: she looked up the safest place for me to pull over and get some rest. I still remember the La Quinta in Bakersfield, wedged somewhere between the Sequoia National Forest and a Vallarta Supermarket, where I spent the night. In some ways, the move could have felt like a regression (during previous arguments, I’d spent nights at other hotels and friends’ houses), but instead it felt like a rebirth. When I woke up with a clearer head, and my younger brother there for emotional support (he took the day off to drive up and meet me), I realized that geography wasn’t the problem—nor was it my ex. The problem was me, and what I’d been willing to put up with. From that day forward, I channeled my inner Selena Gomez and decided I deserved better, and refused to settle for anything less. I hoped Meera was in the same headspace. She asked me whether there was still time left to find her soulmate. I told her that of course there was, although I wasn’t sure we had the same definition of the word. I believe there’s a very limited number of men or women who can be right for any one person—and if you’re with one of them long enough, your feelings might become indescribably de ep, rendering happiness with another impossible. Essentially, you aren’t born with a soulmate, but under the right circumstances, someone can become yours. Meera thought that perhaps she should shift priorities to consider a person “good enough” instead. This philosophy is a hotly debated one, and more nuanced than the phrase itself suggests. I did think Meera was too focused on a superficial checklist, and could benefit from weighing a man’s consequential qualities more heavily, but that didn’t have to correspond with “settling.” I told her as much. “But what if the right guy for me doesn’t exist?” she questioned gingerly. “He does,” I said, refusing to fuel her need for self-pity. “How do you know? What if Trevor is the One Who Got Away?” I stared at Meera blankly, trying to figure out whether she was kidding. She broke a smile. “Okay, so he didn’t ‘get away.’ I got rid of him. But if the right guy for me does exist, then where is he?” “I can’t tell you where he is, Meera. But I can probably tell you more about who he might be.” I considered what I pictured for her. “I see you with someone around your age. Maybe mid-thirties or so. Someone close with their family, well traveled—more for work than wanderlust, probably. Practical, but who finds your romanticism endearing. Kind of the weight to your balloon, so to speak.” “A weight doesn’t sound too fun,” she interjected. “It is if you’d float away otherwise! Or get pecked to death by a seagull.” “Are all your metaphors usually this morbid?” she wanted to know. “About half of them.” I smiled. “Okay.” She sat de ep in concentration. “Does the weight look like Chris
Hemsworth?” “It could.” I managed a laugh. But I told her I thought she was still too focused on looks. Attraction matters, but not if that’s paired with toxicity. I’d been waiting patiently for Meera to show signs of progress, but until she got to the root of why she was so drawn to problematic matches, the only movement she was going to be doing was back into their arms. I suggested to her that she might not even realize the range of men she could be attracted to if they possessed the right energy or personality. “I’m over thirty, Jaydi. Don’t you think I’d know by now?” Kent is almost sixty, I wanted to shout. She also never had the experience of dating as the most confident version of herself, which I stressed to her would be a game changer. “Then,” I shared, “the most attractive thing about a person would be that they recognize your value.” “I hope I get to find out,” she said with a twinge of sadness. “You will. I know that sometimes, going on all these dates feels like spinning your wheels. But one of these days, you’re going to experience the last first date you’ll ever have.”