We all met on a Sunday afternoon at The Grove, an outdoor mall in L.A. that your fav B-list celebrities go to get “caught” on camera. We hit Nordstrom then split up: Stephanie to shoes, Deshawn to lingerie and I, to clothing. Thirty minutes later we had scored three cute shirts and one awesome pair of black boots for Steph. Meanwhile, Deshawn kept busy with a bra specialist and racked up a fitting room that would’ve made Dita Von Teese jealous. Because we were long beyond done with our own shopping, Stephanie and I sat on a tiny bench by the mirrors and waited for Deshawn to reveal each look.
“I’m so proud of her,” she said. “It’s, like, she’s come so far.”
Sensing this was my moment to check in I asked, “How are you feeling about your progress, Steph?”
“Honestly, I’m really disappointed in myself. But there’s so much going on in my life it’s hard to make time to date. There just seems like a million things that need my attention.”
“You have no prospects?”
“I mean, there’s a cute new guy at my job that just started and there’s my trainer that I think is so hot.”
“So, girl why aren’t you pursuing him? And trainers are a part of your ideal-playmate hit list, so that sounds perfect!”
“I can’t,” she said, making a pouty face.
She looked and sounded like the same Stephanie who walked into my apartment on day one months ago. I nodded and assured her that she didn’t have to force some kind of dramatic after-result if she wasn’t ready. I realized then that the clothes I bought her, while cute, were not going to be transformative. A cute shirt and some heels can’t pump up a deflated sense of self, neither could all the books, quizzes and hacks. Again, Stephanie still had to make a decision about the direction of her destiny. Unfortunately, no matter how much I wanted to guide her, that journey was a one-lane, single-passenger road.
Deshawn stepped out of the changing room in a soft pink number that made her 38 DDDD boobs look like a straight 10. She put her hands on her hips and turned from side to side, so we could see it from all angles. Stephanie and I stared at her body carefully as we discussed the fit of the bra. I noticed that no matter how invasive our stares got, Deshawn did not seem self-conscious or bashful about her boobs, or the body they belonged to. As confident as I am with my body and chest (or my lack thereof) I’m not even sure if I could stand that kind of focused attention without making some self-deprecating quip. But there was Deshawn, bravely and bodaciously soaking it all up.
The following Thursday, Deshawn left directly from work and boarded a plane to the unknown. It was the most terrifying, ballsy and inspiring second date I had ever heard of in my thirty-three years on this planet. Final assignment, complete.
Little did I know, travel had also been on Courtney’s mind. She had gone home to Dallas to visit family a few weeks prior, which I knew. But what she hadn’t told me is that she had met someone there.
“I’m sorry I didn’t share this with you,” she said as she held a cup of tea on my porch. “Half of me didn’t want to jinx it and the other half just wanted to keep it sacred—something just for us.”
When Courtney went home, she reflexively went on her dating apps and stumbled upon River. By this time, she had become a pro at cross-checking playmates with her job listing to see if it was worth her time. This guy seemed to check out.
So, on her last night in Dallas, she met up with River for a quick bite that ended up turning into a long-ass date.
“Can I see you tomorrow before you leave?” he asked. River leaned forward and touched Courtney respectfully but intently, which happened to be her love language.
Courtney smiled while retelling the story and then she cleared her throat and got serious. “So technically, I’ve already finished the last assignment. I’ve been on two dates with a high-interest playmate, but nothing is going to come of that, so now what?”
“But you’re from Dallas and you go back there often,” I said. “So why can’t you just keep in touch and see each other next time you’re in town?”
She explained that their connection was too powerful and because of that, the distance was already proving too painful. In fact, they had agreed to stop speaking to each other to save themselves the disappointment.
“We unfollowed each other on social media and agreed to be respectful friends. It’s crazy, I feel like I’ve had to break up with someone I never even got to date, and that’s also why I didn’t say anything, because I don’t even know how to feel about it.”
I disagreed with Courtney and gave her the speech that I’ll gladly give to you, reader: do not save yourself from the disappointment of a great thing coming to an end. Spoiler alert: everything ends! In fact, every single one of you reading this book will die!! Too morbid? Okay, I’ll scale back. To me, the joy of being a person lies in our moments of extreme emotions: love and heartache, grief and creation, failure and triumph. These pinch-me moments, when we can’t believe our own reality, are really what our whole, crazy lives are all about. As I often say to my clients, “Feelings are an immense privilege and if you’re going to avoid them, you might as well hang up the whole people act and become a cupcake instead.”
That’s a little silly, I know. But, it’s the truth. Every single conscious thought you have is a gift! And a special, bold asterisk goes to the feeling you get in the face of potential love.
In your final awesome days of raging on this incredible planet, I fail to see any circumstance where you’re going to choke out the words, “I’m so glad that in my twenties/thirties, I chickened out and avoided that person that made me feel alive.”
Even today, when I think back on the inconceivable disappointments that love has awarded me with, I smile because that is exactly what those experiences are to me: awards. The award for Puppy Love on Acid went to my nineteen-year-old self who “got engaged” (you know, the kind without a ring) to my boyfriend because I was leaving Coppin State University early and for some reason, promising my forever seemed more logical than saying goodbye (hey, Ovan). The award for Most Ridiculous Leap for Love went to the time I spent all the money I did not have to fly to Miami to go on a date with a guy who did not know it was a date (hey, Reggie). The award for Best Cringe-worthy Screenplay Based on True Events went to the countless poems, short stories, articles and unsent texts I wrote to Mark in the wake of our unfinished love story.
These experiences made me into a woman who has boundless respect for intimacy, pools of empathy for others and unbridled hope that there is no such thing as love lost. The heartbreaks were hard, but also they were unavoidable by-products of meeting the right people who were, in hindsight, wrong for me. Now, I’m not going to lie to you and say I don’t regret any of my past relationships. There is a much-different-book’s worth of experiences about men who taught me lessons that I didn’t need to learn the hard way. But in all those cases, whether I would have admitted it at the time or not, I knew the water was too hot before I dove in headfirst. So, it would be one thing if Courtney wanted to avoid River because she heard warning bells, but instead, she was running from the distant but distinct sound of wedding bells. And in my opinion, if you hear them when you’re in the presence of a good person, no matter how far or hella far-fetched the idea seems—go toward them.
She stared down at her cup for a long time then said, “I’m scared.”
“That’s okay, I do tons of shit that I think is scary, this program being one of them! But I still did it.”
“All right,” she conceded. “But I’m still going to keep looking for someone who’s local.”
Courtney left my house that day with two things: first, a vibrator that stunt-doubled as a necklace called the Vesper by Crave because I thought she needed a release, and second, she departed with clarity on what to do next. She and River spoke that night until they had to say good morning. They decided to see each other, at least one more time, before the month was up—but true to Courtney’s word, that wasn’t going to be the end of her sto
ry. A couple of days after that, she was at her favorite juice spot when Derek, a firefighter who she had been drooling over for months, walked in. She knew his name because like at Starbucks, they yelled out orders; she knew his occupation because on one occasion, he had arrived in uniform. And today, she decided, was the day that she’d gather much more about the fine fireman than that.
She struck up a conversation with Derek that flowed so effortlessly, the question “Would you like to go out sometime to get to know each other?” seemed as natural as asking for a napkin.
Later that night she called me in a panic: Derek had said yes to a date and River had set a date to come to L.A. to see her. Now what? I smiled in recognition that lack of supply and too much demand yielded the same reaction from her. Courtney, I had come to lovingly learn, was simply someone who needed order and a healthy level of predictability. If she had a process, she would make progress. So, I decided to try something unconventional to help her achieve that for her final assignment.
I created a step-by-step plan, based on everything we’d learned thus far, that she could use on her date with Derek. (Remember their date from the beginning of the book?) Go back and read that now—I promise it will be better the second time around. Courtney went on a second date with Derek the following week and while she enjoyed him, she wasn’t consumed by him. This had a little bit to do with Derek being too reserved but a lot more to do with River. With his flight booked, they had no reason to slow things down. Their conversations became more intimate and they had undeniable physical chemistry that could even be felt over the phone.
When River arrived, Courtney and I didn’t speak that weekend nor was she posting from her office on social media as she usually did. So Monday night, when I knew he’d left, I released all restraint and made the call.
“I’m dying to know, how was it?”
She sighed in that Disney princess way that’s usually followed up with a song led by a crab. “Amazing. It was honestly not a single drop short of amazing.”
For the next hour, Courtney and I chatted about things that I responsibly cannot share, not just because it’s not my story but because it wasn’t completely hers either—it was theirs. I can say for certain, though, that the feelings, firsts and epiphanies she experienced with River broke her, but in the best possible way.
When we had covered the weekend’s happenings from every angle, I expressed how in awe I was of her. We then said our goodbyes and I realized, with joyful reverence, I had to say one more: it was time for me to step aside as the primary intimate guide in Courtney’s life. I’ve never been a teacher, but I imagine letting Courtney go was a lot like graduating your star student. Half of you is happy to have had a hand in whatever amazing things they will do next and the other half wants to give ’em an F so they’re forced to take your class again.
There is only so much you can learn about romance objectively and if you really wanna become a masterful seducer, ain’t nothing like the real thing, baby. Don’t get me wrong, I’m not cuing the graphics guy to etch “Happily Ever After” over Courtney, or any of the women in the group’s story: time still had a LOT of telling to do. But the truth is, even if the River did run dry (oh, come on—how could I resist!) and proved to be no more than a single chapter or even just a footnote in Courtney’s memoir, without a doubt he was her next great love story.
Deshawn got back from London and texted me that she’d landed safely, but that she was pooped and would call me tomorrow. Nothing else. Not even a shred of a clue how it went.
Damn that tease, I thought.
The next day I got the call that of course I did not miss. And I’ll spare you the wait I had to endure; it was incredible: great chemistry, great conversation and yes, people, for the first time in forever, Deshawn had great sex!
When I asked her what she liked most about the experience she said, “I liked that he didn’t try to discourage any of my crazy ideas. I told him on Saturday that I wanted to live in a romantic comedy, so he picked me up at nine A.M., we went for a really long romantic walk in south London, we went for brunch, we went shopping, and when it got dark we went back to my Airbnb to watch a movie, then . . .”
My favorite part of all was her ease. Unbelievable, sorry-who-am-I-talking to-again?!? ease. The transformation in Deshawn was so dramatic, to this day I’m not convinced she wasn’t a plant. When I spoke to her, she seemed mature, calm and wise beyond water preservation.
“What happens now?” I asked.
“I really don’t know and it doesn’t really matter,” she said. “I enjoyed my time, I stand behind my choices and if he wants to keep talking to me, great, I enjoy talking to him. But if the distance is too much, then I’m grateful for everything that it was. As is.”
We ended the call shortly after that mic-drop moment. She thanked me and promised she was just getting started. Most miraculously, all of this occurred without any giggling.
I’d like to say that I cried that night in joy for the three incredible women who had exceeded my expectations, as well as their own. But you’re more than likely asking the same question that I was . . . what about Maya and Stephanie? Statistically, I was aware that at least one person wouldn’t complete the program but Cherise made sure to secure that spot some time ago. Four out of six I could stomach, but a 60 percent success rate just wouldn’t cut it.
I texted Stephanie and invited her out for a night of Boba and playmate hunting. After she got off from work, I picked her up from her apartment, then we headed to Equinox. Not to work out, not to hang out at the juice bar, but so we could park outside, open up multiple dating apps and put our search radius on 0. Once we found a good parking spot, we set up shop and tag-team swiped for an hour.
Again, if you do your job listing from Chapter Eight correctly, your final description should reveal an archetype of who you’re looking for. For example, Stephanie was looking for a personal-trainer type—hence why we parked outside of Equinox. When I’ve told people about this strategy in the past, they’ve often given me a speech about not limiting your options for love. Which is a fair argument, but I counter that by saying you’re not limiting, you’re zoning. Think about it like this: when you choose a major in college, it’s because after a certain number of years of education, it’s logical that you can make an informed decision about the kind of job that you’d like. You’re not committing to a career, but you know the subject that you enjoy and understand best. Similarly, in dating there comes a time where you know what type works best with you, so why not honor that knowledge by focusing in on that community?
I’d love to say I made this genius idea up but it’s not 100 percent my brainchild. When I went to school for sexology in San Francisco, my school had the craziest library of sex and relationship books. There was endless rows of titles I’d never heard of from people who were probably dead and that’s how I stumbled upon a 1969 bestseller that touted itself as “the first how-to book for the female who yearns to be all woman.” The book is called The Sensuous Woman, and it was anonymously written by a person who went by J. I can see why someone wouldn’t want their full name attached to it; I’d best describe it as an equal mix of vile ridiculousness and pure delight.
Amidst its problematic parts, it has classic lines like, “Pay attention to his kissing style. If he attacks your mouth with enough force to make you fear he’s going to jam your front teeth down your throat, he’s going to be even more cloddish in the advanced stages of lovemaking.”1
Also, the author J offered the story of a woman named Barbra who had a systematic approach to bagging her boo. Barbra wanted to date an engineer because she loved the quiet, solid and introverted nature of the ones she knew. But she currently worked as an administrator in theater. What’s a girl to do? Barbra quit her job, found a position at an engineering firm, started frequenting all social events, yada yada yada, married an engineer.
Using the search radius in dating apps is just a version of that system.
As we
swiped on a bunch of buff guys with deep quotes in their bio, I had a great time with Stephanie, as I usually did. She always taught me new words, had great books to quote and was an excellent listener. But maybe I hadn’t been listening to her, because midway through our session, she casually said, “Like I was saying, things just started to pick up. That one guy, I turned him down because he didn’t want to do the first date on my terms, which felt great. And the guy I did go on a date with, Shan, it’s crazy but I really liked him. We went to this speakeasy and we just had the most natural, good time. It’s been so long since I’ve been into anyone, I just wanted to bask in that feeling. He clearly wanted to hook up, but I just felt like making out and damn, it was so good! I’m surprised I resisted.”
A little while later, we called it a night. But as I had learned, she didn’t technically need this night at all. Stephanie was doing fine on her own.
Next, I had to check in with Maya who had yet to report anything new to me in weeks. To get her back in the groove, I asked around my circle for upcoming lesbian nights. Thankfully, my friend Rachel Scanlon had the perfect suggestion: a comedy night called Two Dykes and a Mic. Maya said she was down to roll and I decided to share the flyer with the group in case they felt like tagging along too.
To my absolute surprise and glee, Stephanie wrote back:
I actually wish I could but, I’m going on a date ☺
Pricilla, Maya and I attended Two Dykes and a Mic and laughed until the drinks in our bellies were clapping along. The all-lady lineup just gave the whole night a fresh vibe as each comic got to step on stage as an individual, not as a representation of an entire sex. Rachel of course was a riot. I’ve seen her perform several times and she never disappoints. There was also one other comic in particular that I strongly suggest you look up: Aparna Nancherla . . . OMG LAHOL (submitting laugh all hell out loud to replace LMFAO, which I’ve never liked). Seriously Aparna, have my babies, you’re so damn funny.
The Game of Desire Page 24