The Inner Monologue For most of the trip, I was able to relax and enjoy reconnecting with Dave. I relished the time away from the city, and having a clean bathroom devoid of medicine, needles, and gauze pads. For the first time in a while, I also hadn’t felt preoccupied with client-related logistics, as Lauren had kindly offered to “take over” during my vacation. It was nice to prioritize my own love life without having to simultaneously juggle everyone else’s. But as Dave drove home, true to form, I found myself immediately wondering how my clients’ dates went that weekend. I refreshed my inbox curiously, but no updates had come through yet. So instead, I closed my eyes and allowed my mind to wander. The change I had seen in Kent this last session, however slight, was motivating. It was a good reminder that even when I don’t notice immediate progress with someone, it doesn’t necessarily mean my advice isn’t resonating with them—as evidenced by his willingness to tackle his “Dating Persona” on his last date. Once clients start doing this, I usually see significant change in their dating habits and results. Some nervous dating habits could be indicators of larger issues (e. g., not giving the other person a chance to speak might suggest narcissism, or shutting down a bit might signal social unease), but I don’t believe most daters are manipulative or undesirable candidates for partnership. While that’s important to ascertain, so is whether or not someone is well suited for you: something that can be easily missed if your date’s behavior is affected by nerves. Conversely, you don’t want your date misinterpreting your character or intentions either. So what are the most common nervous dating habits, along with their accompanying personas, and how can we best combat them to achieve our desired result? In addition to “Babblers” such as Kent, I regularly encounter “Bares,” “Clams,” “Stiffs,” “Workaholics,” and “Self-Sabotagers.” Everyone loves talking about themselves, but for a Babbler, monologuing is a crutch. They typically feel pressure to fill silences, whether that’s by trying to make someone laugh or impress them. (A subcategory of Babblers, aka Boasters —name-droppers and braggarts compelled to tell you what important people they know, or how spectacular they are—are motivated by the latter. A Jewish client of mine, referring to a doctor applauding himself on their date for all his charitable works, told me she was turned off by him “competing in the Mensch Olympics.” This nervous dating habit is occasionally driven by insecurity—after all, if you were confident in what you had to offer, you might be inclined to show it rather than tell it.) Silence can be an opportunity to regroup or even connect with someone nonverbally, but unfortunately, Babblers d eprive themselves of those experiences. If you’re a Babbler, try waiting for your date to speak first occasionally. If they don’t, and the silence is too much to bear, sip a drink or even excuse yourself to the restroom. You should also ask more questions to allow your date to do more of the talking. This demonstrates that you are present, and that you care. (Otherwise your date might go home feeling as if they learned so much about you, but that you had little interest in getting to know them.) If you’re unsure what to ask, pretend you have to write an essay on one of your date’s hobbies or interests, and your date is your only source. If they enjoy diving for scallops, for example, ask who turned them on to it. Did they go on any expeditions recently? Do they usually do this activity alone, or with a friend? The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead by the “questionologist” Warren Berger offers
some thought-provoking questions, not only to help improve your interpersonal communications, but also to improve your relationship with yourself. (I recommended it to Kent, who r eplied: “You think I have time to read, Jaydi?”) The psychologist Arthur Aron also has a fantastic list of thirty-six questions designed to lead two people toward a more intimate relationship, something he created following a 1997 study he conducted at the State University of New York at Stony Brook. I’ve tested it firsthand and can assure you: it works! If you’re on a date with a Babbler, I recommend playfully pointing out their behavior to them. A former client, and dating expert in her own right, Gabi Conti, did this skillfully on her first date with her husband. After barely coming up for air the first hour, he asked her if she wanted another drink with him. Her r eply? “I will only have another drink if you start asking me questions about myself.” Unaware how he’d been coming off until then, he quickly apologized, and the tone of the date shifted completely. It turned out he’d been having an off day, and appreciated her candor. (If his response had been rude, Gabi would have moved on to someone new. And she wouldn’t have minded either, since her now-husband was coming off as too self-indulgent anyway!) When clients shoot down second dates with Babblers who are otherwise amazing catches, I’m disappointed. After all, if someone is chatty on their date, it’s usually a sign they’re excited and having fun with you. If you can overlook their nervous tendency to ramble, they can truly make great partners (I would know: Dave is one!). Babblers are usually outgoing and have interesting stories to share that will entertain you for years to come. If you’re someone like me who enjoys a mental break from time to time, allowing someone else to take the lead in conversation can be relaxing. It’s also worth noting that a Babbler might also be eloquent in other situations, such as at work. For these reasons, and many more, I usually push my clients to grant second dates to Babblers if everything else feels in alignment. Another Dating Persona to look out for is the “Soul Barer,” or “Bare” (not to be confused with the gay subculture “Bears”). While Babblers talk too much, Bares share too much. When opening up, they mistake their feeling of vulnerability for actually forming a connection with someone (“I felt comfortable baring my soul to them; therefore they must be my soulmate”). As a result, they have a tendency to engage in longer dates, which on the surface might feel exciting (“surely our date is going well if this person wants to be here with me this long”) but is ultimately not the best indicator of potential. As a result of oversharing, a Bare can also give the impression that their lives are full of hardship. Naturally, if you had a traumatic sexual encounter when you were younger or your dad was recently diagnosed with cancer, you’ll likely want a partner who can eventually help shoulder the weight of those burdens. But you want your date to learn about you, not just what’s happened to you. If you can’t let loose for a couple of hours, and withhold more personal information until date two or three, you might inadvertently give off the impression you have trouble having fun. When describing their ideal partner, the two most common traits straight men usually request are positivity and lighter energy. There’s a reason people refer to that giddy, post-date feeling as “floating.” Most people want to end up with someone whose life appears generally happy. Heavy topics such as health issues, exes, and prior trauma might indicate otherwise. This doesn’t mean you should change everything about your personality if you’re naturally more serious or lead with your intellect, but everyone has some kind of baggage. (Some people’s just weighs less than others’ or accompanies them on private jets.) Before someone knows whether they want to take on yours, they need to know how they feel about you. So, who are you? It’s a simple question with a very complex answer. But unless you know, your date can’t be expected to, either. If you’re out with a
Bare, you bear some responsibility to guide the tone and pace for the first date and beyond. Ke ep the initial meetup light, and don’t exceed more than two hours with someone. In fact, if you get the sense you’re on a date with a Bare, give them a polite heads-up that, while you’re happy to be there with them, you have a hard out. This should help them ke ep their vulnerability in check. If necessary, you can also redirect the conversation. If talking about the death of a Bare’s father is sending them down a rabbit hole, consider asking where their dad is from or what his favorite movie was. That person will likely feel relief moving on to a slightly lighter subject. This only applies to the early stages of dating, though. I’m not suggesting anyone be an insensitive dummy! If redirecting the conversation isn’t working, they might be oversharing as a way to push your relationship with them forward, all while avoiding real vulnerability: behavior that research professor, author, and motivational speaker Brené Brown describes as “floodlighting.” If your date insists on treating your time together as a therapy session, this is probably a character flaw rather than a nervous dating habit. Being with a genuine Bare has benefits, though. Oftentimes they’ve been through difficult situations—ones they can’t help but divulge to you. And being with someone who’s experienced hardship can be comforting. If you have too, you might experience an emotional connection more easily with them. If you haven’t, you might feel safer knowing you’re with someone who weathered a storm, and hopefully emerged the better and stronger for it. They’re also potentially someone who won’t run away during conflict. And if they were vulnerable enough to share their experiences with you, this likely means you’ll have a partner who will always be truthful down the road—if anything, to a fault. If you suspect you went out with a Bare, try an activity for your second date. It’s a great way to organically get to know each other without the pressure of heavy conversation. By the third date, if they’re looking to open up to you more, I’d not only encourage that, but also plan to do the same in return. Next, some people don’t talk too much or say too much on a date: instead, they say too little. I call those who shut down when nervous “Clams.” Daters like Meera can be confident as all hell at work, but face-to-face with someone they like, a different personality emerges. Surprisingly, many of my on-camera clients (actors, hosts, broadcast journalists, etc.), who are extremely comfortable performing publicly, often have trouble “turning on” that version of themselves on dates. Even when asked a question, sometimes all they can manage is nervous laughter. This shyness is exactly why Clams like Meera should avoid Bares. After all, what better opportunity for a Bare to work their magic than hours of conversation with someone who often forgets to speak? I’ve discovered tricks for Clams to open themselves up, though, and I’ve worked on some of them with Meera. Before a date, ask yourself: what do you love most about who you are that you’d want a potential love interest to learn too? (This question also helps with constructing online dating profiles.) I have a client who’s Ivy League educated with her MBA. She’s a master at Octordle, a trivia night champion, part Venezuelan, and she holds three citizenships. She also has a beautiful smile and lights up when any of those topics come up. But if she shuts down and doesn’t discuss any of it, I’m not sure why anyone would want a second date with her. So, for Clams, going into the date knowing exactly what you’d like the other person to learn about you can help. Changing locations is useful too—even if that means taking a bathroom break to regroup. Alternatively, if you and your date have finished your appetizers and entrées, you can propose to skip dessert and grab ice cream a few blocks away instead. Not only will your spontaneity likely be appreciated, but you’ll also get your blood flowing again—maybe just enough to get your tongue flowing too (in more ways than one)! If you’re on a date with a possible Clam,
it’s helpful to remember that just because they’re shy with you, it doesn’t mean they aren’t outgoing with friends or family. So how can you tell? Patience is key. Allow lulls in the conversation to see whether they’re willing to initiate. And try to be encouraging so they don’t feel judged (because yes, they’re likely aware they’re being too quiet and desperately racking their brain for the best thing to say next). Clams can have a hard time talking about themselves initially, but they’re usually okay speaking about other subjects. Was there a lot of traffic coming here? How ’bout those Mets? If all else fails, teasing will usually do the trick: Are you always this quiet? I’m guessing from your silence you must really like me, huh? The teasing, as long as it’s playful, will show you’re interested in—and not turned off by—their behavior. Clams are often living in their own heads, so getting them to crack a smile will always help make them more present. A Clam might actually be socially awkward, or introverted, but in either case remember: just because they’re more reserved than you doesn’t mean they aren’t worth knowing. Some Clams are the most interesting people in the world, and can make really ideal partners. Then there’s others like me: “Stiffs.” Before my Confident Era, just before I met Dave, I would act really formal on first dates, and men found me hard to read. Unlike Babblers or Clams, Stiffs’ defense mechanisms have nothing to do with how much or how little we say: it’s how we move. We sit up straight, sip our drinks, and adopt a general attitude of “formal is normal.” What is not normal, however, is for our dates to feel like our connection with them has potential. Stiffs can also appear intimidating. The more interested in you we are, the more formal we might act, and the more formal we act, the less interested in you we may seem. What we do have in common with all the other Dating Personas, though, is that our behavior jeopardizes our chances of getting another date with someone. In the past, if I was lucky enough to get a second, I’d usually relax more at that point, and it was “game on.” Like other Stiffs, I can be playful, warm, and generally delightful once that side of me is coaxed out (and I think I’m worth the effort!). But had I been able to unleash that side of myself when I was younger, on my own—well, my prospects would have grown exponentially. The pandemic actually helped me recognize and address my Stiff behavior. Conducting countless intake interviews and coaching sessions on Zoom forced me to see myself more often, and it was easy to see why others had claimed I’d been hard to read. I had a very clear “resting bitch face” (RBF—a misogynistic term for the unpleasant, and usually unconscious, expression one might have when not feeling a particular emotion at all). My RBF had been pointed out to me before, in jest, so it was something I was aware of. But encountering it headon made me realize it was time to make a change. Through conducting Zoom sessions in “gallery mode,” a feature that allows you to see yourself along with other participants on-screen, I started working on my expressions more. What felt like a wide, forced grin at times was really only the corners of my lips slightly turned up. Making that feel natural would take time, but fortunately, facial expressions can be learned through a combination of observation and practice. Over time, and with enough attention to it, people started perceiving me to be generally happier and more welcoming. My outsides were finally matching my insides! Because that strategy worked for me, I started prescribing Zoom dates as practice to my Stiff clients. By seeing themselves on dates, and learning how to adjust their facial muscles and posture, they could actually train their bodies to respond as they hoped them to in situations with higher stakes. (And potentially save themselves years of Botox in the process!) For Stiffs, it’s also important for us to know what makes us smile widely. Maybe we love talking about our n ephew or last vacation to Mexico, or maybe it’s the latest episode of Love Island. Either way, it’s important to identify what those subjects are, and make a point of bringing them up to potential partners.
Expressing passion isn’t the same as exuding warmth, but it does elicit similar energy—energy most people find attractive. Lastly, while clothing choice can affect everyone positively, it’s integral for Stiffs. When I’m cold, for example, I’m much more likely to act uptight. Most people associate sweating with nerves, but cold sensations are even more common for people with anxiety. If I dress warmly in jeans and a sweater, I’m ten times more likely to feel at ease in my environment. This doesn’t mean you shouldn’t dress your best (if you’re a Stiff and you’re convinced you’re going to impress more by strutting into a restaurant in a minidress and heels in the winter, at least bring a jacket to throw on after that first impression is made). Ultimately, though, I advise Stiff clients to wear what makes them feel like them. After all, it won’t matter that they’re showing off their boobs if they’re being a complete boob on the date. Should you ever find yourself on a date with a Stiff, I implore you—don’t assume we aren’t interested in you. Look for clues that a Stiff might actually be engaged on your date. Are they asking you questions? How’s their eye contact? Are they leaving the date early, or are they staying to talk to you more? What happens if you go on a walk with them? Does their body language or intonation change once they’re in motion? Stiffs, once comfortable, are often the most affectionate daters of all. But you’ll never get to see that side of us if you write us off as disinterested. “Workaholics” are another Dating Persona I encounter regularly. These business professionals and creatives have trouble getting out of “work mode.” Without realizing it, the majority of all their stories and references on dates wind up circling back to their jobs, and in worst-case scenarios, they even check work emails on the date itself, unable to “turn it off.” An Oscar-winning director client of mine was often guilty of this. He’d write to me afterward that he wanted to see his dates again, but the women he went out with were regularly shocked to hear that feedback. “He left after forty-five minutes,” one complained, “and he was on his phone the entire time. He told you he liked me?!” Dates with Workaholics can feel rushed and demoralizing. While these men or women might be impressive, if they can’t even prioritize a date for a couple of hours, one might wonder how they could possibly maintain a healthy relationship. Everyone wants a partner they can admire, and some people are specifically looking to be one half of a “power couple.” But most singles I work with are more likely to admire their eventual partner because of that person’s kindness, self-assuredness, or love of family rather than for what they do for a living (provided there is stability, passion, and drive behind it). If you’re a Workaholic, you don’t need to tone down your accomplishments or aspirations. But just as hardships don’t define Bares, successess don’t define Workaholics. So, what can you do to get out of work mode? First, try to avoid scheduling first dates after work. If you’re not stressing about your job all day, you’re much less likely to bring that energy to a date. If you have to go on a date from work, at least change your clothes first. Like Stiffs, Workaholics can be strongly affected by what they wear. An agent I work with is known to show up to a casual date in a suit worn to work that day. And an on-set teacher I coach was guilty of not changing into something more date-appropriate prior to going out. No matter how much she tried leaving work life behind her, shifting from educating a twoyear-old to flirting with a thirty-two-year-old was all the more difficult when she had spit-up on her shirt. If you’re a Workaholic, take advantage of the walk or the drive to your date spot. Can you queue up a Chappell Roan song or favorite crime podcast that makes you forget about your boss you want to kill? Listen to that as you leave work, and whatever you do, don’t check those outstanding emails after pulling into the parking lot. If you’re on a date with a Workaholic, it’s hard not to feel somewhat offended that they aren’t solely focused on you. But this distraction doesn’t make them a bad partner—it
simply means they might need a little help unwinding. If you end up being the person who can do that for them, by sharing a drink or making them laugh, you might just find a very special person on the other side. The director I mentioned is a gregarious natural leader who unwinds on the most epic of ski vacations. He’s now a wonderful father to his newborn son, a proud homeowner, and a great listener once he learned how to put down his phone. Last is the only persona you want to avoid entirely: “Self-Sabotagers.” They ruin dates before realizing their potential, and are guilty of rejecting others before they can be rejected themselves (think those who swipe right on dating app profiles, only to lose interest the moment that person matches with them back). They also have a tendency to interrogate their dates: Are you over your ex? How many kids do you want? When do you want them by? Do you get along with your family? If someone winds up passing their test, it might already be too late: that person is too turned off by them. Self-Sabotagers also rarely enter into relationships, because their search parameters are too rigid or based on absurd premises. A client once told me she wanted an unusual-looking partner: “The uglier the better. I want all eyes focused on me when I walk into a room.” A TV writer acquaintance “knows” that his future wife also works in the entertainment industry and isn’t open to introductions outside of that. One podcaster shared that her ideal type is “Cluster Bs,” referencing men with certain personality disorders. And I even coached a guy obsessed with dating sims, a video game subgenre popular in Japan, who was too shy to attempt actual dating. (I’ve toyed with prescribing dating simulators as “homework” for certain personality types, as some are very well written and have actionable, positive takeaways.) If a Self-Sabotager does get into a relationship, the complications don’t necessarily stop there, as their unchecked patterns are bound to r epeat themselves. Unfortunately, the only predictable future for Self-Sabotagers is that they will likely remain single—at least without doing proper work on themselves. Coaches and therapists can help with that, but you should probably wait to date that person until they’re in a better headspace. I have a soft spot for Self-Sabotager clients like Callie, because they clearly want to be in relationships (otherwise, why bother paying for matchmaking or date coaching?) but often don’t realize how they’re getting in their own way. I felt I was finally starting to get through to Callie, and was confident I could help her in time. But with her self-imposed ticking clock, I worried: would there be enough of it left? Callie was responding well to my new tough-love approach, but she was progressing slowly. While she’d finally stopped resisting the matches I curated, once in front of them, she continued to act more like their interviewer than a possible love interest. In one case, she was even borderline rude, making her disinterest to them clear. “You’ve got it all,” I bemoaned to her. “You’re confident and can flirt like nobody’s business, but you’re grilling people like they’re your meal instead of your actual date, and you’re still not getting to know them—at least not in a real way.” I brought up exit surveys I conduct with clients whenever they meet their significant others outside our service. Roughly half the time, clients wind up with someone who checks off all their major boxes. The other times, noticeable “asks” are missing—yet both sets appeared equally happy in their relationships. That’s because long-term happiness with a partner is not predicated on having all preferences met. It’s about avoiding the dealbreakers. “I could only introduce you to men and women who check off all your boxes,” I attempted to placate her, “but that doesn’t mean you’ll have chemistry with them.” No one was trying to sacrifice quality here. “Shorter men, older women, women carrying extra weight, divorcées with kids, men with receding hairlines... all of these outliers have an equal shot at making you blissfully happy,” I emphasized, “if all the other
components are in place.” Callie nodded, sharing that she’d always told her friends that divorced people make the best partners. “At least you know they can commit!” Daters in some outlier categories also tend to excel in other areas. For example, single moms tend to be more nurturing. Men who aren’t as tall tend to be more charismatic or display higher intelligence (because they aren’t able to rely on their height to get by—take short kings Tom Holland, Dave Franco, and Kevin Hart, for example). Callie reminded me that she had to be attracted to the person she was going to spend the rest of her life with. I agreed, but added that she might be surprised by whom she could be attracted to. Right now, Callie still seemed very set in her ways, and she was going to have to be much more open- minded if she was going to find her forever partner. As it stood, she had merely graduated from writing people off before meeting them to writing them off afterward. To drive home the point, I asked her to think back to a recent Hinge date she rejected. He was a traditionally attractive lawyer who likely could have given her a run for her money on the pickleball court, but she’d been overly distressed by his enthusiasm for aquariums. It was a rarefied interest she didn’t think that she could connect to, and so she had blanketly decided there was no future with him. “You have to admit it’s a weird hobby,” she said as we analyzed her decision to cut him loose. “It’s unusual,” I acknowledged. “But if you had established more of an emotional connection with him, I bet you wouldn’t have cared if he was”—I paused to look back at her email about him, wanting to quote her words exactly —“‘too into freshwater fish.’ You’re still looking for reasons to rule people out instead of ruling them in.” I told her I wanted her to leave room for someone to surprise her or teach her something new. I also insisted she remain present and engaged, even if she was leaning toward not seeing someone again. They still took time out of their evening to be with her. Dismissing someone so quickly not only sends a message that you aren’t interested in another date with them; it also conveys disrespect, implies they have nothing valuable to share, and sends the message you’re devaluing them as a person. “Maybe their roommate is a perfect match for you,” I appealed to her more selfish instincts, in case being viewed as kind wasn’t enough incentive. “There’s no way they’d ever suggest an intro, though, if you were rude.” Callie cocked her head and nodded, acknowledging my point. She explained that she hadn’t wanted to waste anyone’s time, or lead them on, if she didn’t see a connection going somewhere, but admitted she never considered how her behavior might be perceived or internalized by another. She assured me she’d try harder moving forward to get to know her dates better, if only for their potentially cute roommate.