By the time I moved to New York City at 18, Sex and the City had been off the air for years, and I already knew full well that I shouldn’t expect any part of my new life to resemble Carrie Bradshaw’s. There would be no walk-in closet lined with Manolos, no single newspaper column that could pay for all those brunches with friends. And that was fine. I split a dorm closet with my roommate, wrote for the school paper, and caught up with my friends over dining hall waffles. It was blissful. Except for one thing — where was the revolving door of interesting dates? Every week, Carrie and her friends went out with someone new, someone amazing. I couldn’t help but wonder where to find guys like that. But that changed last month, when Candace Bushnell — the writer of the dating column Sex and the City is based on — hand-picked three people for me to date.
Candace (the OG Carrie Bradshaw) teamed up with Match (the OG dating site) during the first week of January by joining the site’s Experts Picks team, which suggests compatible matches for users who pay $4.99/week. Match offered me three picks for free. I couldn’t imagine a more perfect matchmaker for me; not only did she shape two generations’ views on dating and relationships, but she also created the blueprint for my career — I (obviously) write about dating for a living, too. Prior to working with Match, she even set up a few couples who wound up getting married. I was curious to see who she’d choose for me.
To get started, I created a Match profile, uploading photos and sharing details about myself and my ideal partner. One major difference between Match and other apps? You can go long. While Hinge limits each answer to just 150 characters, Match lets you have up to 4,000. Writing my profile felt like stretching out on a lounge chair after years of being crammed into a plane seat with zero leg room.
Next, Candace checked out my profile and sifted through the site’s users to select three potential matches for me. She shared them with me over Zoom. “I was reading every single word they wrote, looking for clues about how they present themselves. I sensed you’re looking for a serious relationship,” she said. (True.) “I felt like these guys had their lives together and were looking for something real.”
Her first match was Jordan*, a business owner and dog dad who packed his profile with details about himself (“I’m a very open-minded risk-taker who’s always up for an adventure”) and his ideal partner (“down-to-earth, athletic, smart, goofy, ambitious, great travel companion...”), ending with, “If you've read this far and there is some interest, please send me an email, don't window-shop. I don't bite. Well, only on the third date. LOL.”
Candace explained, “He wrote a lot. He was thoughtful. He knew who he was and I think that’s so important in a relationship. It seemed like you two would appreciate that in each other. I thought you guys could really be a cute match.” My instant reaction? I wanted to meet him.
Next up was Oliver*. In one photo, he looked sharp in a gray striped suit; in another, he showed off an Australian toy shepherd, an intricate chest tattoo, and a shocking number of abs. His “two truths and a lie” were smoking a joint with Rihanna, owning a couple of sloths as a kid, and visiting Iceland six times; his interests included wine and cheese (love) and nutrition and fitness (I mean, fine). “Looking for that one-life stand,” he wrote. Noting the suit, Candace said, “I don’t think being well-dressed is superficial. He thinks about how he presents himself to the world. And you know what? If you live in New York, you’ve got to think about that, because every time you leave your apartment, you’re on the biggest runway in the world.” The thing is, he actually lives in Jersey City, a subway and train ride away from me in Brooklyn. As cool as he seemed, I wasn’t up for the distance.
Finally, there was Mateo*, who works at a startup and identifies as spiritual. “Nothing’s more attractive than someone you can laugh with and count on no matter what life throws at you,” he wrote. Candace loved that. “I’ve been in a lot of relationships and that’s really one of the most important things, because sh*t happens and you’re like, what the f*ck? You have to laugh,” she said. “That’s why I picked him. I felt like this guy’s got heart.”
Rather than getting coffee or drinks, Candace suggested going for “new and exciting” activities. “Those kinds of situations spark attraction. If they’re willing to engage in something new, they’re willing to have a relationship, because that’s what a relationship is: doing stuff together, not just sitting there like a lump.”
Since the Omicron variant was still surging, I decided to lie low and wait two weeks before reaching out to Jordan and Mateo. But by then, Mateo had deleted his account. Jordan never responded to my message. So... I was stuck.
This was especially a bummer because my recent string of dates had ranged from blah to bad. There was a coffee date so devoid of chemistry, I wondered if I had accidentally wandered into a job interview. One man psychoanalyzed me using a quiz he had learned from his therapist ex-girlfriend. I had a blast with another guy, but he was nine days away from a cross-country move. Most recently, I had a dinner date with a man who asked me a grand total of zero questions about myself, but repeatedly explained the intricacies of his new favorite hobby, a medieval farming game he plays on his phone.
Not wanting to let Candace’s expertise go to waste, I decided to test out her advice about dates in new settings. I had recently matched with Andy* on Hinge. His profile said, “The one thing I’d love to know about you is what you’re currently reading.” I messaged him to say I had just finished a book and was planning to head to a bookstore soon; I asked if he had any recommendations. “Yeah, I have a suggestion,” he wrote. “Take me with you.” I’d never been on a bookstore date before — that was new! As an author and bookworm, the prospect of getting to know someone while browsing aisles sounded extremely sweet.
We met at my local indie bookstore, McNally Jackson. The fresh setting really did make a difference. Right away, he gravitated toward the Biography and Sports sections, which sparked conversations about his interest in presidential history and his childhood spent on the baseball field (his brother played Little League with Pete Davidson in Staten Island). Rather than just telling him what I do, I could literally show him my own novels right there on the shelves. After circling the store, I bought a book, and then we walked to a nearby bar. I thought it was a pretty great date: we easily talked for hours; there was flirty chemistry and a goodnight kiss. Before parting ways, we planned to meet again.
The next day, though, I remembered something he had said within minutes of meeting me. Knowing full well I write rom-coms, he said, “I don’t think fiction is as valuable as non-fiction.” In the moment, I had offered my own perspective, but 12 hours later, the comment bugged me. It was rude, not to mention wrong. We were texting back and forth, and when I happened to stumble across an article about a book club for men who read romance novels, I sent it to him, writing, “This reminded me of our conversation about fiction.” In the piece, the men all said that reading romance helped them become more empathetic, more comfortable expressing their feelings, better listeners, and even happier in bed. I thought it was fascinating. Andy apparently didn’t. He didn’t text back for four days. By that point, I had soured on him. It wasn’t just his comment, it was also his silence. On top of that, the more I reflected on our date, the more turned off I felt by other things he said, including some of his views on politics. There was no second date.
Candace was right earlier when she said I was looking for a serious relationship, but I don’t need that to happen tomorrow. I’d be happy to have fun and adventures along the way... except lately, dating hasn’t felt fun at all. It’s like a never-ending game of lining up connections only to watch them fizzle out. I called Candace again to get her perspective.
She wasn’t fazed by my lack of recent luck. “In the old days, there were maybe only five eligible people in your town. Today, people feel like there’s a whole world out there [on dating apps], so they can have more experiences that don’t work out,” she said. “Listen, I'm single and I'm 63, and you know, I still have moments when I'm like, ugh, it’s hopeless. But that's not real. Emotions are not real life. They don't really have anything to do with the facts. The thing to do is just try to look at the bigger picture. I mean, this is a moment.” I liked her perspective. Just because things might be bleak today doesn’t mean they’ll always feel that way. In fact, they probably won’t.
In the meantime, she suggested leaning on my friends. “When I was writing Sex and the City, I had a lot of girlfriends, and we talked about our different dates all the time, and we laughed about it, and that was really what got us through it,” she said. She also gently suggested an attitude adjustment. “It’s really important to create a positive attitude by looking at the positive in your life. And remember, there’s an element to meeting somebody that’s honestly just luck. It’s about being in the right place at the right time.”
She also gave me feedback on my date with Andy. “You brought him to a place that wasn’t neutral. A bookstore is one of your places. It probably made him feel really insecure. What do guys do when they feel insecure? They put the woman down to make themselves feel better. When I said go and do something new, I meant something neither one of you have ever done, not something where you have the advantage.” Fair enough.
But my favorite takeaway from the conversation was this: She said, “You’re not just a single person looking for another single person. You’re a person who is looking to enrich and expand your life.” That could come in the form of meeting someone special, but it doesn’t have to. I know Candace’s life expanded by penning a column that inspired a deeply beloved TV series, writing 10 books, and most recently, creating her own one-woman show, Is There Still Sex in the City? I’m sure it’s been enriched by her meaningful friendships, and her two poodles, Pepper and Prancer, and her daily bike rides. Isn’t that enough?
Maybe my luck will change soon, or maybe it won’t. Either way, it felt good to know that Candace has been in my shoes, too. (Still not Manolos, but that’s OK.) I was ready to see this moment in a new light.