* * *
Everyone who meets her, platonically, is thrown to hear she struggles romantically because (modesty aside) she’s the full package: she’s smart, she’s fun, she’s interesting, and heck yes, she got skills in the bedroom and boardroom! She’s the funniest one of all her friends, the career overachiever and the Michelangelo of winged eyeliner. She’s read self-help books, has cultural interests, knows what bills are currently being voted on and even knows all the lyrics to Hamilton . . . but despite it all, maintaining romantic attention has been a massive struggle for her.
* * *
I doubted she knew all the lyrics to Hamilton but in many ways, this was Stephanie. Except, Stephanie had stopped believing that she was this person. Between feeling like she was a disappointment and her disappointing launch into adult love, her confidence and sense of direction seemed to be shot. Stephanie seemed to put herself second in fear that she would never be anyone’s first pick.
To confirm this, when I asked her what she felt she needed to work on she confessed, “I’m really accommodating. I often just mask my own preferences to the point where I don’t have a personality, and that’s boring.”
This goes back to the age-old question: Why do nice people finish last? My answer is because people don’t differentiate people pleasing and having a character rooted in confidence and kindness that is pleasing to people. Having a character rooted in confidence and kindness means that you find joy in being good to others, which makes it easy to sniff out and discard people who don’t have good intentions. People pleasers, on the other hand, are so consumed with their desire to belong that they relinquish their right to be respected. Based on Stephanie’s recountings, it was evident why she’d become the nice woman at the back, but I was confident that I could work with her to bring her up to speed. I thanked her for her time and circled her name, then went back to my balcony to remind myself what outside felt like.
I woke up on the final day of interviews, checked my dry erase board and thought Shit! I already have my five candidates: Maya, Deshawn, Courtney, Pricilla and Stephanie.
There were still over fifty women I had yet to meet, and aside from my solid five I had plenty of backup options, like a sweet twenty-six-year-old transgender graphic designer with a tiny lisp and huge heart as well as a forty-seven-year-old diplomat who would have been perfect had her job not been so strict. Half of me wanted to say fuck it and cancel all remaining calls but the other half knew that I had to see this phase through to the end. So I adjusted my attitude, made another vat of tea and set an intention to whip through the remaining calls like a telemarketer. Perhaps the storyline of the women I’d already chosen could be combined so that I could make space for someone new?
In light of this, I’d like to retro-apologize to anyone I connected with on the final day of my search. After a few calls I realized I sounded like a wacky casting agent for Jerry Springer: “Say, are you a thirtysomething bossy property manager with a ten-year-old son that you wish admired your love life? No? Any chance you’re an awkward environmental engineer struggling to accept her weight gain while trying to figure out how to deal with your anxiety so you can start dating in the queer community?”
I tried my best to keep the calls especially short so I wouldn’t get too attached to any of the remaining women, which was hard since most were sweet and super-interested. That’s why I was intrigued when I connected with Cherise, a thirty-seven-year-old, bald-by-choice, white collar professional. She spoke to me like I was the person at the call center she had to tolerate in order to save money on her plan, but I guess in her defense, she really did feel as though she had been cheated in the love department for a long-ass time.
“I haven’t been in a relationship in over five years and I haven’t met anyone decent in that time either,” she said, irritated. “The last guy I kind of dated I met at a music festival among mutual friends. I have no real idea why it ended, it just dropped off like a cliff and I for sure wasn’t heartbroken. It was the most un-spark-having-ass dating experience I’d ever been on.”
“What drew you to applying to take this summer-long course with me?” I asked Cherise as I had done with everyone else.
She smiled for the first time. “I’m told I’m intimidating, beautiful, strong, bold, smart and it seems all this greatness continues to keep them away.”
OH. OKAY.
I’d love to point out just how many times in my four days of casting that I heard the words “I’m too intimidating” (in other words, me, I’m super fly, too super-duper fly/ I’m Supercalifragilisticexpialidocious) in answer to the question, “Why are you single?”
Not that this reasoning isn’t true, but anecdotally I’d say it’s probably actually true 5 percent of the time. The other 95, someone is chronically single because they are narcissistic or grim or desperate or clingy or a windbag or conceited or avoidant or unstable or a pleaser or terrible at partner selection. In short, most people who can’t find or keep love are in that predicament because they’ve got some work to do, not because they’re too perfect for anyone to work with.
She paused for a while and I considered cutting the call short like I had been doing all day. But then she continued, with tears in her eyes and a voice that was totally different than the one she’d began with: “I’m tired of being looked at but never seen. I want to express that at this point I know I must be doing something wrong and I’m willing to do what it takes to fix it. I’m sick and tired of waiting to be loved.”
After we ended our chat, I thought about Cherise for a long, long while. Cherise was also a cactus woman, who failed to see the disconnect between who she presented herself as and who she hoped others would see. But in that final moment of our call I saw her walls come down and it was strikingly beautiful. It was clear that Cherise was going to be a challenge to my third criteria: They must work well with others. But I truly felt up for this one.
After the last call I was a blissful pile of exhaustion and exhilaration, but I remained in my office for a while longer to reflect and clean. I removed the piled-up dishes, candy bar wrappers and tea mugs that kept me afloat throughout my marathon of interviews. Then I cleared my whiteboard, which was littered with notes, to make space for six important names: Deshawn, Courtney, Pricilla, Stephanie, Maya and finally, Cherise.
Six was certainly not my original plan and it put a wrench in my budget, but who doesn’t love a wild card?
That night, I had incredible celebratory sex with Jared, who had been expertly giving me extra space over the previous four days. I’m an ambivert who needs alone time in order to gain strength to perform extroversion; he understands that and me in a way that I didn’t think was possible. And to me that one little word, understands, encompasses all the joys of finding your person(s). I was excited, grateful and (I at least thought) prepared to help the six selected women capture that feeling for themselves.
After a great night’s rest, I returned to my desk and drafted an email with the subject line: You Had Me at Hello—Let’s Get Started!
2
Single and Terrified to Mingle
When the day of our first group meetup arrived, I was one giant cocktail of nerves, adrenaline and spaghetti (I would have chosen a better meal for the big day, but your girl had leftovers to finish).
I thought about what I wanted to wear for the entire week, pivoting between a two-piece power suit and a bodycon dress before I realized I was going about this the wrong way. This experiment was not about impressing others, it was about being seductively comfortable and noticeably impressed with yourself. In order to be successful at that, you must try your hardest to make it appear that you are not trying. This may sound confusing but, in the end, it will make sense: effort needs to be both the primary, and secret, ingredient in your game.
Therefore, when the big day came, I slid into my standard Netflix-and-chill look: horny makeup (which we will cover in Chapter 5), “messy” hair, minimal jewelry and relaxed but still pressed-ou
t clothes.
As scheduled, the first knock came at 11:30 A.M. I opened the door wide with an even wider smile but jerked a touch when I saw Pricilla, the mom of our group. Her makeup was done as though it were 11:30 on a Friday night but her outfit, jeans and an oversize hooded sweatshirt screamed Saturday-morning errands. Perhaps she had gone through the same debate as me but instead of a happy medium she went the mullet route: party up top and bummy on the bottom.
“Great smoky eye,” I said as we walked into my living room.
“Thanks,” said Pricilla shyly.
“So what’s your son up to this weekend?”
“With his dad,” she said, as someone simultaneously knocked and pushed open the front door.
I was greeted by the gummy smile of Maya, who wore a T-shirt that had whales and penguins swimming in outer space printed on it. Maya was an interesting character: she didn’t do her eyebrows or wear makeup, and if I’d had to guess, all of her clothes had at least two previous owners. But despite her casual casing, she also struck me as the last person I’d want to get on the wrong side of. Among the group, she was the youngest, with the least romantic experience, but based on our brief interactions, I’d also say she was the strongest and the most likely to put you in your place.
Shortly thereafter Stephanie, the late-blooming academic, and Courtney, the stern property manager, arrived. Courtney wore glasses and a yellow tank top that was an exceptional choice against her dark complexion. Stephanie had on jeans, flip-flops and a checkered off-the-shoulder shirt, which—spoiler alert!—was an outfit I saw a lot during our future months together. The colorful-haired scientist Deshawn was running late, and my wildcard addition, Cherise, still hadn’t completed the onboarding paperwork so she couldn’t attend that day.
“What do you guys have planned for the weekend?” I asked, trying to fill the dead space.
A better icebreaker for nervous guests would have been: What does an ideal weekend look like for you? This gives people the opportunity to talk themselves up without any time constraints because maybe they don’t plan on being awesome this weekend, but everyone has done something awesome at some point . . . and if they haven’t, you’ve given them the space to make it up.
Right on cue Stephanie remarked, “I don’t know yet, I’m kind of boring.”
“Yeah, same,” echoed the group, as they all avoided eye contact like I was an eclipse.
“Come on, there has to be something going on?” I pressured awkwardly.
Saved by the knock, Deshawn arrived then said her hellos. “Sorry I’m late, did I miss the introductions already?”
“No,” I said as I smiled at her and the group. With all parties seated, I launched into a speech welcoming them to the program, which, as I told them, was easily the most exciting (and terrifying) project in my years as an intimacy educator.
“By the time we are done working together, I want you to know how to flirt and connect like you know how to walk and talk,” I continued. “I want you to be in the driver’s seat of every intimate interaction you have. While this program is about love, dating and romantic connections, what we are trying to accomplish is much bigger than that. You aren’t just here to find a boyfriend or girlfriend, you’re here to learn how to make powerful and memorable bonds with everyone you choose, effortlessly.”
The room was still for a bit, but Deshawn fixed that with a nervous laugh. “Yeah, good luck with the effortless part when it comes to me.”
“None of us need luck, we need commitment and the right attitude. Actually, let me ask all of you a question: What kind of person do you think remains in control and on top at all times?”
Deshawn began, “The person with the most knowledge, I think.”
Maya continued. “Uh, the person with the most confidence?”
“Maybe the person who is shameless, I don’t know if that makes sense or not,” said Stephanie.
“The person who works the hardest,” said Pricilla.
“I would also say confidence,” added Courtney.
I jumped back in. “The correct answer is nobody. You’re not here to learn how to be undefeated, you’re here to become a champion. And to do that, it’s impossible to come out on top every time. And when you don’t, you have two choices: you can lose, or you can learn. So yes while ultimately I want you to be winners, to get there you have to commit yourself to being an even better learner.”
“What kind of things are we going to be doing?” asked Pricilla as she tugged on the strings of her hoodie. “Like I said in my application, I don’t feel comfortable with blind dates.”
I softened my tone. “No one has to do anything they don’t want to, but I do encourage you to approach this with an open mind. You’re not going to get different results by doing the same things.”
With a few of the women smiling and nodding, I decided I had done enough talking. I asked them to introduce themselves, and in light of Deshawn’s and Pricilla’s reactions, I also invited them to share any additional fears they had.
Maya was sitting closest to me and even though her nervous eyes pleaded for me not to, I gestured for her to go first. She sat up straighter but kept her eyes low. “Hey, I’m Maya. I work for a startup company but I’m an aspiring writer and, um, yeah, there’s really not much else to say. I am very nervous about this experience but I’m also just a very nervous person. I have no idea how to even begin to process about what’s going to happen except that I’m also excited to see who I become at the end of this. I have, like, no experience dating. So this is probably one of the biggest life steps for me, maybe.”
Courtney went next without prompting. “I’m Courtney, and I am a property manager for two buildings. Listen, y’all, here’s a life hack—be a property manager. You get to live rent-free and you get flexible hours.”
Everyone laughed and Courtney smiled then continued. “I’ll admit that I’m terrified to hear what people really think of me. Like, I want to hear it, but I don’t want to hear it. Does that make sense?”
“Yes!” exclaimed Stephanie. “I feel like Courtney articulated how I feel perfectly. I’m a newer dater. I just started dating, like, three years ago. I’ve experienced some failures and I think I’m normal and I’m cool and I like me, but I’m also like, well, maybe there’s something to be said about the way I am dating or who I am that is impeding me. And maybe whatever that is, is so obvious to everybody else.”
I nodded and kept my mouth shut since I had decided not to reveal the step-by-step plan of the program to the group. But between you and me, in the not-so-distant future we would address Stephanie’s and Courtney’s fear of direct criticism in the most terrifying way possible.
“As for me,” continued Stephanie as she exhaled, then looked away, “there isn’t a ton to say. I work for the government but I’m not, like, thrilled at my job. My life is pretty basic. I’m trying to lose weight and get myself together. I guess this is a part of that whole process.”
My face twisted instinctively. Actually, there was a ton to say. Stephanie was an Ivy League grad who worked for the court system. She had a brilliant mind and a wandering spirit that had led her to take up residence in New York, South Korea, London, Switzerland and L.A.—all within the past five years. There were many more fascinating parts to Stephanie than her negative opinion of her body and her body of work.
Pricilla went next. “I’m Pricilla. I’m a hair-transplant technician and I’m also trying to lose weight like Stephanie, but I’m also really excited about what everyone is nervous about because I wanna pinpoint what’s wrong so I can fix it. The only thing that would make me nervous would be, like, blind dates.”
I asked the obvious: “What’s with the big fear of blind dates?”
Pricilla tugged harder on her hoodie’s strings until she was practically choking herself. “Blind dates give me anxiety because I feel pressured to be interested or I’ll make the other person feel bad.”
Pricilla was so self-sacrificing that she se
emed guilty any time that she had to take up any attention. But I learned through prying and social media investigating that she had the kind of life worth taking up space to gush about! For example, she easily could have talked about her awesome relationship with her son or the fact that she had worked as an assistant to Steven Seagal. She even lived in Russia for three months, since Mr. Seagal happens to be homies with Vladimir Putin.
Next came Deshawn. “Hello again, everyone. I was born in California, I love Beyoncé and I also work for the government.”
I wanted to smack my forehead. Deshawn was technically also a government employee, yes—but she wasn’t a pencil pusher, she was an environmental engineer working to end California’s water crisis! Clearly, we needed a crash course on the dangers of downplaying. Being humble and undervaluing yourself are not the same thing—and believe me, they yield very different outcomes.
“As per this process? Well, I am most afraid of finding out I’m not, like, cute awkward but really awkward. To backtrack, I grew up knowing that I was weird . . . but, like, normal weird. Then I went to engineering school and I was only around people who are extremely hard to talk to and extremely uncomfortable, so I fear I may have adopted some of those personality traits and now my awkwardness has escalated.”
I smiled in acknowledgment and gave her a once-over as I thought about what she had said. Deshawn struck me as sweet and outgoing so I personally would not describe her as socially awkward but I could make an argument for her being physically awkward. Her hair sat in a curly coif above her ears and was dyed a combination of colors that seemed to match her braces. She wore an overly loose bright-patterned outfit with the wrong bra, which kept her busy as she pivoted between readjusting her shirt and folding her arms over her chest. She also had a large hoop nose ring and several other piercings in her ears. From my vantage, Deshawn was a visual concoction of too many colors, materials, movement and metal. If I had bumped into Deshawn on the street, I would have assumed she was a quirky teen who was late for her part-time job at Chipotle, not an environmental engineer. That had to change.
The Game of Desire Page 4