Here’S Looking At You, Kid
Kent was troubled by the away message in my email. “You can’t just disappear on me,” he responded
obstinately. I leaned back into my pillows and groaned. I’d been recovering from a polyp removal
surgery—necessary to pr ep me for an additional round of IVF—but it seemed Kent interpreted my need
for self-care as a personal affront. Natasha, the taller bachelorette he’d been excited about, canceled on him
last-minute before what would have been their third date, and he was insistent on processing her
“rudeness” with me. While I normally would have stood my ground—or in this case, my bed—I agreed to
hop on the phone with him later that day to talk through it. The gesture wasn’t entirely selfless. I was,
truly, curious what he’d say. I had some insight from Natasha, who’d emailed me as well, hoping to
explain “her side.” Supposedly, on their second date, Kent spilled the tea on all his previous matches and
his exes—including the mother of his two kids. (I’d already lectured him about discussing other
relationships this early, but apparently the advice didn’t stick.) He not only dominated the entire
conversation, regaling her with work tales in an effort to impress her, and opened up about his relationship
with his father in an effort to appear more vulnerable, but to my exasperation, he also
dropped the “L-bomb” in an effort to... well, express love. At first, Natasha had been flattered. But after
processing the bizarre experience with several of her girlfriends, she came to the shrewd conclusion that
Kent’s declaration had had nothing to do with her. He barely knew her. So rather than acc ept his Tom
Cruise moment as a precursor to marriage, she saw it for what it was: a red flag. Wow, I thought. Maybe
she could have a word with my girl Meera. “Are you okay?” Kent greeted me. “You don’t sound too
good.” “I’m fine,” I r eplied curtly. I considered telling him about the tests doctors were running to find out
the rec eptiveness of my uterus, but thought better of it. He quickly moved on to his favorite subject:
himself. He monologued about everything—challenges with his latest movie, California’s harvest
season— everything exc ept his date. I smiled politely as he hammered on about his nightly ritual of
picking grapes (apparently, wineries like his usually harvested between midnight and early morning due to
the cooler temperatures, which helps stabilize sugar levels and maintain the fresh fruit aromas—who
knew?) and asked where I lived so he could send me a bottle of his latest Chardonnay, an offer I
appreciated but respectfully declined. I didn’t anticipate Kent showing up on my doorst ep anytime soon,
but preferred to ke ep the details of my home life private, including my address. (Lauren, however, would
have had no qualms acc epting the gift. “He could find me on Zillow anyway,” she’d say. Plus, her nine
months of forced sobriety were now over. “Bring it on!”) By the time our conversation finally got around
to Natasha, Kent had worked himself up to detail everything wrong with her, along with the fickle nature
of women in general. And then, before I could challenge his troublesome core beliefs and offer him some
guidance on his impulsive tendencies, he said he had to run. “I’ve decided to take a break from
matchmaking,” he declared, almost as an afterthought. Wasn’t he the one who was just annoyed about me
disappearing? I sat up quickly, only to feel a sudden pain run through me. This is what I interrupted my
recovery for? I knew by now that clients request dating breaks for a variety of reasons: travel, work
schedules, or even insecurities—like the prior winter when Meera
was “feeling fat” and wanted to wait until she’d lost a little weight so she could feel more confident. (I
tried talking her out of it anyway. She could work toward dropping the weight if that’s what she wanted,
but there was no reason not to meet men during that process.) But Kent wasn’t worried about his body; he
was worried about his ego. He could have chosen to feel excited that as a team, we were finally tapping
into more of what he was looking for. Instead, he went into self-preservation mode and removed himself
from the dating pool entirely. “So, you’re saying if I meet another woman you might like,” I clarified, “I
shouldn’t tell you about her?” “I’m not saying that,” he started to backtrack. “I’m saying only reach out to
me if you have someone spectacular. Okay?” That’s the only time I ever reach out to you, you nitwit, I
thought. But I was cordial and ended the call politely. As I ran through everything I knew about Kent’s
history, I realized it wasn’t much. In addition to revealing little about his upbringing or family, he’d been
actively avoiding the subject of his prior dating life, which meant I didn’t have many clues as to how he
felt about love, commitment, transition, or, importantly, rejection. Anything I’d been able to piece together
had been from offhand comments made during more conversational parts of our sessions. (For instance, I
knew Kent’s relationship with his ex-wife only became copacetic after she remarried and no longer
required child support—something he’d shared while flippantly referencing her “new family’s” vacation to
Ibiza.) But had he ever been in love with her? Had he ever felt love with anyone? Or was the best for Kent
yet to come? I truly had no idea. What I did know was that if he k ept up this “tough guy” act, he was never
going to wind up happy. He was in touch with his feelings, but perhaps not the right ones at the right time.
The disparaging way he’d discussed Natasha meant he wasn’t in love with her (no shock there), and my
instincts and experience told me that based on his ability to conveniently dismiss his passionate declaration
on their date and sail into anger, this wasn’t the first time he’d behaved this way. I sympathized with Kent.
He felt emotions in a big way. A person doesn’t “threaten” their matchmaker with a dating break
otherwise. But it was
important for him to consider how others might process his big feelings before sharing them so willingly.
It’s selfish not to, and I knew he could do better.
I crawled back into bed later that night and, despite my better judgment, began crafting an email to Kent. I
wished him luck on his solo adventure, and threw in some tips and tricks in the hopes that—should he meet
a fantastic woman in my absence—he wouldn’t blow it by being too intense or talking too much. My
pointers would probably fall on deaf ears (he wasn’t exactly known for his listening skills), but at least I’d
have tried every possible way to get through to him, even if it was no longer my job. I felt like an eager
employee wanting to leave a good impression on my boss even though I’d just been fired. I turned my
computer off and put my phone on silent, sitting in the dark with Dave, who was already asle ep beside me.
Kent’s session today had been a good distraction from my discomfort, but I was mentally drained.
Investing so much time and energy in a client only to have them disappear—temporarily or forever—was
always tough, and it could leave a scar if he ever circled back. The threat of someone checking out is
enough to cause mistrust in any relationship. I knew this firsthand from Dave, and thought about the early
months of our own relationship when a similar threat felt palpable. “I think it’s romantic for couples to
break up and then reconnect in the future,” he’d once told me. “Don’t you think?” I did not think. I fought
a growing pit in my stomach. “Romantic is knowing someone will always be there for you,” I protested.
“How am I supposed to ke ep dating you now, knowing that you’re probably going to break up with me at
some point just because you think it’s romantic?” “Relax.” He grinned, not realizing how seriously I was
interpreting what he thought was a cavalier comment. “You have nothing to worry about. I was talking
hypothetically.” I appreciated the course correction, but the damage had been done. I spent months
afterward slightly on edge, worried about getting too close to him in fear he was going to leave me. I knew
that he’d already sort of ghosted the woman he dated right before me. The two had spent a decent
amount of time together, and while never exclusive, he cut things off with her, seemingly out of the blue.
(He did send a message to say he wouldn’t be seeing her anymore, but no explanation as to why.) When
I’d found out about her existence later, I was shocked. My usually thoughtful and kindhearted boyfriend
had essentially disappeared on someone? “What was I gonna tell her?” he inquired innocently. “That I met
someone else better?” “Not better, Dave,” I’d scolded him. “Better for you. Wouldn’t it have been more
considerate to say that? To at least give her some form of closure?” It’s easy to write off ghosters as
selfish, but it took that experience for me to realize that sometimes, they evaporate in an attempt to spare
feelings. That doesn’t make it okay, though. I believe that most women and men can handle the truth, and
usually, they’ll move on faster knowing it. Otherwise, they’ll be stuck asking questions that wind up
hurting themselves: That person didn’t even respect me enough to be straightforward—am I that easy to
dismiss? Did our time together, however brief, mean nothing? A parting conversation might be
uncomfortable, but not having one can feel worse for the aggrieved party. I thought about a popular
influencer Alanna Noel, whose podcast I’d once appeared on. During our conversation, she mentioned
how she made a regular habit of ghosting men without ever weighing the potential effects of it. “What if
that guy meets someone amazing tomorrow, but he’s in his head now thanks to your ghosting, and doesn’t
work up the nerve to approach her?” I challenged. She was gutted. “I’ve never really thought of it that
way.” Kent did warn me he was going to disappear, which was better than ghosting, I supposed, but if he
were to return one day, I wondered how that would affect our relationship moving forward. At least in that
instance, I’d be getting paid.