I thought about all the energy I’d spent worrying about whether Luke liked me, or if he liked me, did he really like me, and if he really liked me…It was just a never-ending spiral of needing more and more validation, but I barely ever stopped to think about whether he was giving me what I needed.
But now I could feel things changing. Take this one guy, Josh, whom I’d had a nice dinner with at an Italian restaurant near my apartment. We’d kissed, and then I didn’t hear from him, and eventually he texted me to say that he really enjoyed meeting me but he’d gotten back together with someone. No worries, I thought. But then, he resurfaced a few months later and said that he had regretted not going out with me again, that the other woman hadn’t worked out, and could we go out again?
I wasn’t especially physically attracted to him, but I figured, what the hell. Year of yes! And he seemed kind and sweet, the type of guy for whom I thought maybe an attraction could evolve. So I went out with him, and we ended up back at his apartment. He played piano, and we sat at his piano and sang for a while, which was fun, and then had pretty forgettable sex, which was not. In the morning, I woke up and realized: This guy is lovely, but not for me. He asked if I wanted to get breakfast and I said I had to go, and then I told him that I didn’t think it was going to work out between us. But afterward, Josh was persistent—he called and texted, and told me he really liked me. Past Me would have buckled at this point because the idea of someone I could tolerate who was really into me was too alluring. But truly, Josh was not right for me.
Or take Marc Anthony’s bassist. We went on a daytime date at a bar in Los Feliz, and he was charming and cute and smart, and at the end of the date said he wanted to hang out again, and I agreed. But then a game of text tag ensued: Most days he was only available late at night, like after eleven p.m., and then he wasn’t available on the weekends because he was rehearsing or traveling. Instead of bending over backward to try to figure out a time that worked, eventually I just gave up.
Even though I felt like I was becoming more confident and secure with myself, it still took a lot of mental energy to be on all the time in the way that dating requires. My friend Samantha—one of my only real friends at work—had similarly decided that she was tired of dating apps. “Let’s go on a man cleanse,” she said matter-of-factly, sitting across from me in my office one afternoon. “Like, it’s not forever, but we just need to detox. Work on ourselves.”
That was exactly it—I needed to detox. I was still trying to be open, to say yes to people I might have passed over previously, but the mechanics of online dating are basically equivalent to having a very busy part-time job and anyone who tries to tell you otherwise is straight-up lying or hasn’t done it very much.*
First there was the actual matching with people. Then came messaging on the app, a back-and-forth where I was supposed to be witty and flirty and reveal just enough about myself to be interesting without saying too much in case the guy was a serial killer. Then if things were going well and I had determined that he was in all likelihood not a serial killer, we’d switch to texting outside the app. I also preferred to have a phone call before I went on a date, because in the same way a single photo can be incredibly revealing, a single phone call could also tell me a lot about a person. Then there was the whole dance of deciding if I wanted to meet up with him and he with me and finally making plans, around 25 percent of which got canceled or postponed for one reason or another, getting my hopes up for said plans, and if we eventually, finally met up, it was often a letdown to realize that they were just…fine.
During the man cleanse, I started questioning what I was doing all of this for, anyway. What if marriage just wasn’t right for me? I’d gone out with more than thirty people in the year since moving to L.A., not to mention all the people I’d dated in New York. And not one of them was right for me?
I started allowing myself to picture what my life would look like if I was single. I thought about what it would be like to spend holidays with my family and be the only one who wasn’t married with children. Would I be pitied? And was I more concerned about being pitied than I actually was about being single? That is, was I more worried about what other people thought about my being single than actually being single? I wasn’t sure.
Certainly, now, at almost thirty-seven, I felt like my window was starting to close, and I hated that I thought about it in terms of a “window.” I was frustrated by how fixated I was on meeting someone, but part of me also wondered why I should feel shame about wanting to be in a relationship. Wanting love and companionship is a basic human need, and I felt that women, in particular, are framed as being “desperate” if we dared articulate that we actually wanted to get married, especially if we were in our late thirties or older. I wanted to reframe my thinking, to simultaneously be okay with the idea of being single while also allowing myself to articulate that I wanted to find a partner. Was it mental gymnastics? Perhaps. But it was the most honest I’d been with myself in a long time.
* * *
—
A COUPLE OF WEEKS after I had started my man cleanse, I had lunch at Son of a Gun, a trendy restaurant near my apartment, with my friend Heather, who writes the Ask Polly column for The Cut and is just as wise and perceptive in person as she is in her column. “So. Are you dating?” she asked. Heather is one of those long-married people who loves to discuss your dating life, which I normally found voyeuristic and annoying, but not from her—she was genuinely interested in dissecting what was going on.
“Eh,” I said, picking at my lobster roll. I recalled that the last time I’d been to this restaurant I’d been on a date with fish taco guy, and I remembered that the conversation had been pleasant but stilted and that when I subsequently told him that I wasn’t interested in seeing him again, he seemed insulted, as though he had wasted his time taking me out. “Not really. I went out with this guy who was the touring bassist for Marc Anthony, who was actually really interesting, and we had a good time and both wanted to hang out again, but it was basically impossible to schedule a second date because he was always rehearsing or performing, and he wanted to meet up at, like, eleven at night and I’m usually in bed by then! I can’t be meeting someone for a date at eleven, like maybe we will stay out until eleven or even midnight, but does he think I’m twenty-two? Eleven is way too late to go on a date, I guess unless you work nights or something, which I don’t.”
I took a sip of water and continued. “So I texted him, ‘Hey, I had a really great time with you and I was looking forward to hanging out again, but it seems like our schedules are just too difficult to sort out right now. Take care!’ And I gotta say, as soon as I sent the text, I felt a weight lift. I feel like the old me would have gone above and beyond to try to hang out with this guy—I would have met up with him at eleven at night, or whenever he was around. I would have rearranged my life to accommodate his.”
Heather smiled. “I think this is a very good thing,” she said.
“You do?” I said. She seemed enthusiastic in a way I wasn’t expecting.
“Yes,” she said. “You knew what you needed out of a relationship, and even if you were attracted to this guy, you knew that it wasn’t enough. And so you said goodbye.” She looked at me, as though taking me in. “I’m telling you—this is really great.”
“Well, thanks,” I said. “Yeah, you know, now that you say it, I guess I kind of…took control of the situation.”
She smiled again. “I have a feeling that this means you’re about to meet someone you really like,” she said. “It just feels that way. Like now you know what you want, and what you need, and that person is going to materialize.”
“So you’re saying The Secret works, then,” I said.
“I’m just saying—Secret or not, I think you’re finally ready to meet someone. Maybe you thought you were before, but now you really are.”
Skip Notes
&n
bsp; * Possibly worse are the long-married friends who met their partners when they were twenty-two who say things like, “Wow, I feel so lucky that I met Trent before dating apps existed! I’d be so bad at them!” It’s just, like, no, actually, you probably would have figured them out like everyone else, and trust me, I am not particularly enthused about being on them either. These are also the friends who like to grab your phone and swipe for you and then say things like, “You weren’t kidding! These guys suck!” If you have been one of these people, this is just a friendly note that this is really fucking annoying.
CHAPTER SEVENTEEN
The man cleanse had cleared my head—it had been nice to not have to think about dating for a little while. During the cleanse, my friend Emily, my old Gawker co-worker, came to visit for a couple of days. She brought a housewarming gift with her: a tarot deck called the Wild Unknown. “I like to just draw a card every day,” she said, showing me the cards and the book that revealed their meaning. “It’s just kind of like, a guide for the day, something to focus on, how your day is going to go.”
We had a great time—we went to a party hosted by a writer we both admired in the hills above Studio City, we sang karaoke downtown with a few other friends of Emily’s who lived in L.A., and we ate delicious Japanese food. I was sad to see her go.
The morning after she left, I drew a card: the Ace of Cups. It represented love, joy, happiness, emotional fulfillment. I texted her a photo of it and wrote: “Feels auspicious.”
“Holy shit!” she wrote back.
My auspicious tarot card draw notwithstanding, I was reenergized about getting back on the apps. I had a theory that when you deleted Tinder and then re-downloaded it, it gave you “better” options than it might have previously, and one of the first guys who popped up was named Matt who looked kind of familiar. I scrolled through his photos. He had a handsome, friendly face, a really nice smile, big brown eyes. He was holding a guitar in one of the photos. No photos of him with fish, or doing shirtless headstands, or in front of a microphone. His profile was charming and funny, but not in a way that said, I’m funny, laugh at my jokes, even though he was a comedy writer and was thus professional-level funny and good at jokes. Instead, it bragged self-deprecatingly about how he’d been quoted in his hometown newspaper in Massachusetts about the best lobster rolls. Oh! He was from Massachusetts. That was a bonus. My only reservation was that he was only thirty—a full six years younger than me. Better a mature thirty than an immature forty, I thought, and swiped right. I immediately got the notification that we had matched.
I got a message from him a few minutes later. “Hey, I’ve never used this app before so I’m not totally sure what I’m supposed to say, but hi.” I rolled my eyes. I felt like guys claiming that they’d never been on the app before was a common opening salvo, meant to be disarming, and I debated simply not responding. But in the spirit of attempting to be more open-minded, I messaged him back. We went back and forth a few times, then started texting, and then a couple of days later I asked if he wanted to talk on the phone. He did.
He called later that night. It turned out he worked on a late-night show on Comedy Central where my friend Steph also worked. It was a relief that he wasn’t a total stranger, and talking to him felt so comfortable, like I’d known him for ages. He told me about his family—he was the youngest of four, and his next-oldest sibling was seven years older—and about coming to L.A. “I moved here when I was twenty-three because I wanted to write comedy,” he said. “I didn’t know anyone except my roommate.” They lived in Pasadena, he said, and he’d applied to work at the Apple Store and at Starbucks, and the Apple Store got back to him first. So he’d become a Mac Genius at the Apple Store at the Grove and worked there for almost five years.
“Didn’t you get discouraged?” I asked. “Five years is a long time.”
“I had given myself five years to get a job in entertainment, and I did,” he said.
“That’s amazing,” I said. I found Matt’s self-made career extremely attractive. Hollywood is full of people whose parents have worked in the industry for decades, who got them their first jobs as production assistants or in the mailroom at an agency. Matt had done it all on his own, without even graduating from college. He explained that while he was working at the Apple Store, he met people, some of them famous, who’d brought their computers in to be serviced, and he started a podcast with one of them. Eight years later, he was still podcasting, he’d done a lot of stand-up, he’d been a host on a daily TV show, and now was a staff writer on a nightly game show on Comedy Central. I was impressed.
It wasn’t just his résumé, though. There was something about the ease of our conversation that felt…different. And the way that he told me he was impressed with my job was also attractive. I’d gone on way too many dates where I belatedly realized that I had been subtly downplaying my accomplishments or my job because I thought that would make me more appealing. I hated that I had done that. So it was refreshing to feel like not only did I not have to downplay my own résumé, but also that it made me more attractive to Matt. It made me think he would celebrate my professional accomplishments, not feel like they threatened him in some way.
We went out for the first time a couple days later. It turned out he lived down the block from me, so we decided to go to a bar near both our apartments, and he walked over to pick me up. As I descended the stairs from my apartment, I saw him standing in the courtyard, beaming. He was beaming—at me! “You look really nice,” he said, and I smiled.
“So do you,” I said. He was very cute in person, with big brown eyes and a wide smile.
And he was easy to talk to, sweet and funny and disarmingly personal. “I worked in a funeral home for four years,” he said. “My two best friends, they’re brothers, their family owns a funeral home and so I worked there. I also worked in an ice cream shop and once almost got locked in the freezer and all I could think about was that the headline in the papers would be ‘Fat Guy Dies in Ice Cream Shop.’ ” He saw my confused face—he wasn’t skinny, but he didn’t look fat, either—and added, “Oh, I lost a hundred pounds in the past year. In high school I weighed four hundred pounds, then I did gastric bypass surgery and lost weight, then gained some back, and then about a year ago I decided to start working out and eat better.” He was matter-of-fact about this.
“Wow,” I said. I thought back to the summer after Jon and I had broken up, when I became obsessive about exercise and everything I ate, and yet I had never moved through the world as a fat person—just as a straight-sized person who had internalized a lot of messaging about the “ideal” body.
We talked some more—about my family, and my job, and living in Los Angeles, and then, perched on barstools, we kissed. I didn’t even care that it was in front of the bartender.
Matt walked me home, and we kissed goodbye outside the door to my apartment. “When can we hang out again?” he said.
“Um…Friday?” I said. I usually tried to play it a little cooler. I’d also been burned by guys who seemed really eager at first, and then as soon as I showed real interest, they withdrew. So I was slightly wary, but I was also trying to listen to my gut, which was telling me that Matt was different. I was also more willing to take a risk I might not have before because I knew I liked him.
“Great,” he said.
“You choose what we do,” I told him. “I’m leaving it all in your hands.” When it comes to activities, I’m a planner, which sometimes gets exhausting. I wanted to see if Matt could plan something, too.
* * *
—
THAT FRIDAY, Matt picked me up in his car. “So where are we going?” I said.
He grinned. “Disneyland.”
“Okay, wow!” I said. I was into it, but I was a little skeptical—I wasn’t someone who especially loved Disney, nor had I felt compelled to visit Disneyland since moving to L.A. “Is this
a thing people do, go on dates to Disneyland?”
He looked at me from the driver’s seat. “Yeah, of course,” he said. “You don’t need to have kids to go to Disneyland.”
I knew that, of course, but I had always been confused by adults who went to Disneyland without kids. What was the point? But once we got there, I had to admit, it did feel pretty special. I took a photo of Sleeping Beauty’s palace, which sits at the end of Main Street, all lit up. I posted it on Instagram and captioned it: “Typical Friday night hang.” The night was fun and silly and we held hands as we walked around, and Matt introduced me to Dole Whip, and to cream cheese–filled pretzels in the shape of Mickey Mouse. Matt was a Disney expert—he’d been dozens of times since moving to Southern California—and I surprised myself by actually caring about the little bits of Disney trivia he was telling me, like pointing out the names of the stores on Main Street and explaining that a lot of them were the names of Imagineers who had worked on the original construction of Disneyland. Was I now a person who cared about Disney Imagineers? I must really like this guy, I thought.
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