I Wish I Knew How To Quit You “If you’re looking to be off the market in the next ten months, something needs to change,” I started brusquely, already a bit peeved Callie was ten minutes late to our session. While I was sympathetic to her busy work schedule, I was eager for her to make the best use of our time together. “You can’t make babies without taking baby st eps.” Callie didn’t protest. Instead she listened as I explained that even if Jake or Mike or Jennifer didn’t end up being the perfect match for her, I could learn a lot from her interactions with them—observations and judgments that could help lead me closer to finding her person. If she really wanted me to do that, I needed her to start going on actual dates, and soon. “They can come from anywhere, though,” I reminded her. “You don’t have to meet someone through my database, although obviously that would make me happy. But I’m not just your matchmaker—I’m also your dating coach. And I can give you the tools needed to meet the right person, whether that’s through a friend or at the supermarket. But you have to stop judging people and start getting to know them, okay? Which means actually meeting them.” Callie nodded. I had emailed her about my agenda for today’s session on online dating, and she seemed rec eptive to—or at least curious about—what I had to say on the subject. Some singles view apps as the antithesis to matchmaking, but the truth is, a good matchmaker should encourage their clients to supplement their dating life in as many ways as possible. Even if the quality of our matches is generally higher than what’s “out there,” we only know so many people. Besides, if I could help arm Callie with the skills needed to recognize, and not accidentally overlook, the right match on her own, I’d still be a meaningful part of her journey to find love—which was all I really cared about. Callie wasn’t the biggest fan of online dating, which I understood. These platforms boast a wide range of options, but in some ways, they’re also quite restrictive: 10 to 15 percent of bachelors and bachelorettes will receive more than 90 percent of the likes, a phenomenon dating app employees refer to as “hypergamy.” (This behavior occurs in person too. Lauren and I once threw a “game night” for clients so they could meet more than one potential love interest simultaneously, but instead of everyone getting to know each other, all the bachelors and bachelorettes flocked toward the same one or two people they deemed the most “desirable”—usually for superficial reasons. As a result, they were overlooking people they might really have connected with otherwise, and now we couldn’t set them up, because they already knew each other. We stopped throwing singles mixers.) There’s also data breaches, invasive advertising, safety concerns, and sexual harassment to worry about. According to a Pew survey conducted in 2023, women are more likely to have negative experiences on dating apps than men. “About two-thirds of women under 50 said they had received physical threats, experienced unwanted continued contact from a match, been called an offensive name or been sent unsolicited sexual messages or images.” There is also a leading provider of dating services that threatens innovation, which most certainly impacts quality. Match Group holds almost 50 percent of the global market, with their vast empire overseeing more than forty dating companies—including some of the most popular ones: Tinder, Hinge, Ok Cupid, and The League. While these apps are “designed to be deleted” (Hinge’s slogan), these companies are incentivized to ke ep you on them for as
long as possible—after all, more monthly subscribers means more profit for their shareholders. This strategy is made easier by literal dopamine rushes (or surges of the “feel good” hormone) whenever users get notified of new matches, and discounts for paying for a bulk of time up front. (In her Netflix comedy special Single Lady, Ali Wong mentions she almost missed out on a relationship because she’d just spent $250 on an annual subscription to a dating app and wanted to get her “money’s worth.”) There’s also a “gamified” experience that promotes an endless variety of new matches over de epening connections with current ones. The result for many is often superficial conversation that rarely leads to actual dates. The existence of AI also throws a wrench into an already difficult-to-navigate lands cape. Determining which strangers are quality people worth investing in was already a tough endeavor, but now, many people use AI to help boost their profiles or conversation, leading some singles to feel deceived after meeting their dates in person. Tools such as Chat GPT, or even an app such as Rizz, can help people come off as wittier or more charming than they actually are. Others are aware they’re chatting with AI, but that doesn’t always stop them from connecting emotionally with it. On AI chatbot apps like R eplika, users can create and interact with AI companions, including romantic partners. And these relationships can have detrimental consequences beyond unhealthy attachments. A Belgian environmentalist wound up committing suicide after his chatbot, Eliza, convinced him to sacrifice himself to save the planet. (AI also offers positives with online dating, such as Bumble’s “Private Detector,” a tool that blurs explicit images, and their “Dec eption Detector,” which identifies fake profiles—but the downsides are hard to overlook.) Despite these challenges, there was no denying online dating was still, statistically, the easiest way to meet someone. “But my guy would never use an app,” some clients tell me. Really? I ask. Even if it’s not in their nature, after a decade or so of not meeting the One, eventually they might try using it, and don’t you want to be “findable” when that happens? I don’t intend to dismiss “the burnout,” because online dating—equivalent to having another full-time job—is an absolute mind suck. But it’s important to stick with it, even if that means leaving your profile active while taking a two- or three-week break and catching up on your messages later; or even having a friend “run” your profile for you. I don’t recommend a friend pretending to be you, which could start off a potential relationship on the wrong foot. Instead, I recommend a friend “taking over” your profile, explaining who they are and why they want to find a match for you. This tactic isn’t overused yet, and is a refreshing way to possibly add new blood to the mix with little to no effort on your part. Plus, your friend, if single, could benefit—just as my friend and Benicio del Toro’s former assistant Jackie did. When she “took over” a friend’s dating profile, she wound up meeting her now husband, an upbeat, Italian manufacturing engineer, Sergio, instead. Initially, Jackie showed her friend Sergio’s picture, but the friend wasn’t interested in meeting him. So Jackie threw her own hat in the ring, and now she and Sergio are married with a newborn. I shared this story with Callie, who lit up at this creative approach to dating. She felt open-minded after our p ep talk, and we brainstormed about the best app for her to start with. Bumble is helpful if you’re in need of good conversation starters; J-Swipe, Christian Mingle, or Catholic Match are strong examples that make dating within your own religion easier (BLK, Kyank, or Dil Mil are solid options within specific races); Grindr and HER are popular among the LGBTQ+ community; and The League is a good resource if you’re tired of the bartenders and struggling actors populating your feed. Coffee Meets Bagel works best for AAPI males, Match. com or e Harmony for singles over fifty, and Raya for fun dating tales starring Marvel superheroes and famous drummers (or if you want to get away with not listing your height). I’m not as
much of a fan of the ones that limit swiping, within reason, as it should be up to each individual to demonstrate restraint. All of these trends have the capacity to ebb and flow, but I encouraged Callie to start with the one I felt consistently hosts the highest-quality singles on it, Hinge (and the paid version, so she could more easily narrow down her search criteria). It has many prompts to choose from, is user-friendly, and what’s written there can usually be applied to all the other apps in case a change is later desired. She screen-shared her profile. I hoped that by going through it, I could finally gain more insight into what she was truly searching for, and help her attract that more easily. The way to win me over is By surprising me, whether it’s with a home-cooked meal (even if it isn’t good!) or tickets to my favorite band. Typical Sunday Peloton or pickleball, brunch with my friends, squeezing in some work, and maybe a stand-up comedy show. The dorkiest thing about me is My obsession with Meg White. I suggested that when we were done updating everything, she should launch her new profile under an alternate email address. If she hadn’t received optimal engagement from users before, more coveted profiles wouldn’t be shown to her now. For the first time since we started working together, I saw Callie take out her notebook. Looking her profile over again, I immediately identified ways she could make better use of the limited real estate provided to her. Swipers subconsciously want to know whether they can envision fitting into your life, but they can’t do that if they’re unsure who you are. Based on what Callie had shared about herself, she appeared to be active, playful, social, and driven. But she defined herself almost entirely by what she liked to do for fun. Perhaps unsurprising, most singles tend to lead with this information, believing it will make them appear more interesting, or that someone might want to connect with them over a mutual interest—but it could also backfire, accidentally alienating someone with different passions. “I just returned from Gabon,” a client once wrote in her intake. “And tracked the elusive African Forest El ephant, in the dense, humid jungle, on foot. I traveled to the Yangtze River in China to glimpse the Yangtze Finless Porpoise, the only living freshwater porpoise in the world. And to help protect the Hawksbill Turtle, I encouraged fisheries to switch to more turtle-friendly fishing hooks. I’ve been to more than fifty countries, and still counting.” This was fascinating information, but what did it really say about her? Did she go searching for endangered wildlife for the thrill of it? To check something off her bucket list? Or did she simply love animals? The why, and not the what, would be more revealing about her character. Bonding over shared interests is a bonus, but remember: Hobbies can be acquired. Shared values and life goals, on the other hand, are far more indicative of long-term compatibility. “So, what would you change?” Callie finally asked bravely about her profile. “I can handle it.” “Well, for starters, you spend the first prompt talking about the way someone can win you over, which would be fine if that actually helped weed out the
wrong people. But realistically, anyone who finds you attractive is going to try to match with you, whether or not they fit the description of what you’re looking for. So it ends up being a waste of space and time. You want prompt responses that focus on you.” Rather than dive in more immediately, I suggested I get to know her even better first. I asked her to ignore the prompts provided, and wondered aloud what she would want her future husband or wife to know about her. Once she knew what she wanted to share about herself, we could reverse-engineer that into her profile. “This isn’t about getting as many likes as possible,” I reminded her. “It’s about attracting the right person, and getting them to engage more once that happens.” I could sense she was starting to feel overwhelmed. “Let me put it another way,” I added after she struggled to answer. “What would your best friend or mom say sets you apart?” Callie laughed. “My mom would say I’m scaring people off. She says I intimidate them.” “Intimidate how?” “Well, I was captain of a kickball league once,” Callie shared. “She told me I was never gonna find someone yelling at teammates to round third.” “So you’re a little bossy. That’s perfect. Also, your mom is wrong.” A future partner would likely find her kickball story endearing. “In fact, you should add it to your profile.” “That my mom thinks I’ll die alone?” “That you were captain of a kickball team,” I said fondly. “And you were more interested in winning than the free drinks afterward. That’s who you are, and that’s the kind of thing that will get your future partner’s attention. They may or may not care that you’re also into The White Stripes.” “Oh, they’ll care.” She smiled. I could tell she was pleased that I’d recognized the reference in her earlier prompt response. “I get it, though,” she added. “Fewer hobbies and interests, more personal stories that showcase who I am.” “Exactly.” Specificity matters too. I shared that I was much more interested in her being captain of a kickball team, for example, than her riding the Peloton along with every other suburban woman in America. I thought about all my other clients who listed “brunching, traveling, and watching TV” without realizing just how generic it made them all sound. They’d be much better off offering some insight into their life and personality. What were their favorite brunch spots, and why? Did they travel home to visit family, or choose a destination based on its number of Michelin stars? And if “watching TV” was such a big part of their life, what shows were they into? Again, think the why and not the what. “Tell me more,” I challenged Callie. “You’re playfully bossy, with good leadership skills. What about a softer side, that only those close to you get to see? I know you have it.” “That doesn’t mean I want thousands of strangers knowing too.” “Maybe not. But you want at least one of them to. Right? And you’ve got a much better chance at that if they get to see who you really are. You’re a good person, but how so? Pretend I’m a judge. What’s your evidence?” “I don’t know. My friends and family think I am?” “Okay. So, what would they say on the witness stand? My best friend drops matzo ball soup at my doorst ep whenever I’m sick,” I used as an example. “Hmmm. I drive friends to the airport? And that’s saying a lot.” (She referenced LAX, the stuff traffic nightmares are made of.) “I volunteer at an animal shelter.” “You do?” I responded, somewhat surprised. “See? I’m learning about you already.” She also shared that she calls her grandmother every week. I banged the pretend gavel, demonstrating a case won. “What are you waiting for?” I instructed. “Put it in your profile!” When she was done, I summarized our conversation. She included the kickball bit, which showed she was active and funny. The airport and grandma stuff proved she had a good heart. Still, her profile was missing one more component. “Can I leave in Meg White?” she interrupted. “Please?” “Sure.” I smiled. “You can leave in Meg White.” I was happy to see her satisfied with how the session was going, but we were far from done. I turned to the
“voice” portion of her profile. “How you share information is equally important,” I added. “Saying you’re funny, for example, is different than telling a joke. You could be witty, de eply insightful, or the smartest woman on Hinge. But right now, your profile could use more personality.” To help her address that, I ran through a series of questions. Are you more sarcastic or cheesy? Bashful or boastful? Do you like to pontificate or get straight to the point? Do you tend to use more slang, or do you consider yourself more formal? She admitted she never really thought about all this before, and I assured her that was normal. But it was necessary that we capture her essence if we were going to attract the right person. “And remember,” I added, “you’re not a monolith—you can be playful and serious, all at the same time. Don’t be afraid to display a range.” I used Meg White as an example, suggesting we include the same information about her obsession, but use it as an opportunity to display another facet of herself, such as her willingness to compromise. “Take the ‘What if I told you’ prompt”—I referenced one of Hinge’s conversational lead-ins. “What if I told you that I’d go to any concert you like if you let me play the White Stripes on our road trip?” Callie nodded, digesting. “See how you’re giving similar information, but doing it in a way that highlights who you are a bit more?” “Well, it highlights who you are.” She grinned amusedly. Like she was in her initial Zoom with me, Callie had been positive and generally good-natured all session, and I couldn’t help but wonder where this version of her had been hiding the last two months. I felt optimistic things were about to take a turn, and I had to give her credit: she was taking my criticism like a champ. Feeling I still had her attention, I shifted the conversation to what prompts to respond to. (A Hinge expert once shared the “54 Best Hinge-Prompt Answers,” and I had to laugh—how is sharing the 54 best anything supposed to help guide someone? My list was much narrower.) As an extension of our conversation before, I suggested eliminating any that put the focus on the other person. I also steered her away from negative prompts such as “You should not go out with me if...” or “Something that’s nonnegotiable for me is...” Putting a positive spin on your wants is important. You don’t want to come off pessimistic. Another useless prompt is “Two truths and a lie.” (I get a lot of pushback on this one, because it’s often the prompt that elicits the most engagement from other swipers. But ask yourself: Is this engagement from the right swipers? Or did you simply present a fun “game” people were interested in playing? While it’s a fun conversation starter, one of your three “facts” listed isn’t even real. If you’re going to attempt it, at least be sure that your truths are more compelling than your lie.) Being straightforward about who you are will usually be more appealing to the right person. I encouraged Callie to use one of my personal favorites: “The one thing you should know about me is...,” “Biggest risk I’ve taken,” or “My greatest strength.” I also recommended prompts that spoke to life goals, since that’s something that can be shared with the person reading it. “Together we could...,” “A life goal of mine is...,” and “This year, I really want to...” are some favorites. I’m also into creative openers such as “Weirdest gift I’ve ever given or received,” “My most controversial opinion,” and “Apparently my life’s soundtrack is...” They’re all layups to show off your playful side. But if you can find another way to convey that within the body of a more seriously framed question, you’ll not only demonstrate your wit but also reveal another, more vulnerable side of yourself in the process—something I was eager for Callie to do. (Since conducting my session with Callie, Hinge partnered with psychotherapist and New York Times bestselling author Esther Perel to create additional prompts. All ten of hers, which fall under the category “Your World”
and range from “I could stay up all night talking about...” to “Something my pet thinks about me” are 100 percent Jaydi approved!) My lesson wasn’t over yet, though. We figured out what Callie wanted to say, and how to say it, but the order of it all was equally important. If she began her profile too intensely, she could scare off the right match. “I like to think about moving through your profile the same way you should date: starting off light, then getting a bit more serious and vulnerable as someone gets to know you better.” I shuffled things around a moment and pulled up the updated version: The dorkiest thing about me is I was captain of my kickball team (and I was more interested in winning than the free drinks afterward). What if I told you that I’d go to any concert you like if you let me play The White Stripes on our road trip? The one thing you should know about me is I call my grandma Sue every week. I also advised her to make her desire for a long-term relationship visible, so she could filter out the people just looking to hook up. Callie agreed, then asked my opinion on her photos. I’d been worried about inundating her, but she was eager for more feedback. I wondered whether she was a glutton for punishment or my best student yet. I reviewed her photos again, and answered truthfully that they were really strong. They were well lit, and she clearly knew her angles well. I typically start with pictures when doing profile punch-ups, because while online dating tends to be superficial, so is actual dating. (At a party, someone is unlikely to approach you because of your kindness and intelligence, since those traits aren’t visible.) Most daters are used to starting with the physical, because often that’s all you can go by, and the same holds true digitally. I suggested that she make the photo of her smiling her main one since it was the most inviting. Approachability is a key part of the process. I once worked with a video game designer who wouldn’t swipe right on any woman not smiling, because, often wrongfully, he assumed she was too serious. He’s not alone in that assumption, though. Callie had a nice mix of close-ups and full-body shots, which was key. Daters often assume, in the absence of one or the other, that someone is hiding something. Photos in sunglasses, hats, or any other accessories that might obscure what a person actually looks like are another common mistake, but her shots didn’t have them. Nor were her photos overly filtered. “I love the one with your girlfriends,” I noted to her, impressed. “It shows you’re social. And you chose a good one where you’re the main focal point.” So many daters recognize the value in sharing a group shot without realizing that including someone else more traditionally attractive than they are might inadvertently turn matches off. Who wants to date you knowing they might have the hots for your friend instead? “If I switched out anything,” I added, purposely nitpicking, “I’d say the last two are a little redundant.” Both photos, clearly taken on the same day, featured her in the same floral dress. I advised her to swap one with another of her in action, on a hike or on a trip—making it more tempting for a swiper to envision themselves in her life. I also encouraged her to make use of the captions, another way to capitalize on available real estate. Utilizing the space would make Callie stand out more, offering a potential match more useful information about her personality and outlook. Lastly, I steered her away from recording a voice prompt. Like the disappointment you feel when a movie character sounds nothing like the one you
envisioned when reading the book, you don’t want someone to write you off because your voice doesn’t match the way they imagined it sounding. Callie had a nice voice, but someone would discover that soon enough in person— while also getting to know the whole package. Swipers are constantly looking for reasons to reject people, so don’t give them one more reason to say no. “I wasn’t really sure how this was going to go,” Callie admitted to me. “But this has been great.” I beamed back at her, pleased she was getting something out of our time together. “By the way,” I added before we wrapped, “if you ever get bored or feel stuck, I’m also a fan of scoping out the competition.” “The ‘competition’?” she r epeated, baffled. “The other men and women competing for the same dates. I wouldn’t do it for too long, because it’ll mess with your algorithm—but for a few minutes or so, change your settings to search for people like you. You can see how others in a similar demographic are ‘selling themselves.’ Might give you some ideas.” “Wow. That’s kind of genius.” I glanced at the clock. We only had a few minutes left, but this was the part I’d been looking forward to the most, and my covert agenda for today’s session: gaining more insight into what she was truly searching for by swiping together. Given her hasty dismissals of my carefully vetted “nominees,” I was curious who, in her eyes, passed muster. And so I watched. Unlike friends and clients with analysis paralysis, Callie was swiping through matches left and right, categorically ruling out people with decent potential in mere seconds. I gently asked her to walk me through her logic. “Well, this guy wears too much hair gel,” she commented readily, or “This one’s eyebrows are too distracting. How could I ever focus on what he’s saying? Oh, and see here?” She stopped on a good-looking guy wearing a baseball cap. “Classic hat-fisher,” she said, referring to some men’s attempts to mask a receding hairline or bad haircut with certain angles or headwear. While she had a point—it’s better for a man to own that kind of thing rather than to catch his date off guard—on the whole, I felt that such strong opinions and reactions up front were unreasonable. “You know he can quit once he has kids, right?” I referred to the skydiver she was about to reject based on his pastime. “Fine. But take this chick...” She scrolled through a woman’s profile sk eptically. “Cute enough, right? But she’s a VP in business affairs.” “So?” “So she should be an SVP by now. At her age?” I held up my hand, forcing her to slow down. “What if she switched professions later in life? What if she’s the most charming woman you’ve ever met who nursed her sick mother back to health and wants kids next year?” I looked at her with genuine curiosity. Overly focusing on someone’s financials is usually a mistake—but if it has to be done, I typically encourage clients to think more about their partner’s earning potential rather than their current income. That kind of selectivity was leaving no room for nuance. What if a person was laid off right before you met them? Or something unexpected happened and they were forced to drain their life savings? These things could happen five minutes into a relationship, or fifteen years into one. “I can’t believe you did it,” Callie told me before we ran out of time. “Did what?” “Convinced me to stay on the apps.” I was relieved, and wondered if after all this time, I had finally earned her trust.