When Jennifer was introduced to the idea of taking a date to couples therapy, mostly she was excited to try something different. The 28-year-old leadership professional had been a serial monogamist for most of her dating life and had recently ended a three-year relationship that turned toxic (her words). These days she’d been going on Hinge and meeting people in the city, but nothing seemed to stick. Dating felt more like a series of fleeting interactions. She hated the way people would disappear, but she herself also never felt hooked enough to pursue more dates with anyone. But she loved self-work, and the idea of taking a date to couples therapy felt like a great way to bypass all of the small talk and the slow process of getting to know someone.

Jeff, on the other hand, was enjoying taking things slow. The 28-year-old New Yorker was known as the fun, sociable one among his friends, that guy always looking to have a good time. He had started seeing a therapist last year to learn more about himself, and it was his therapist who’d encouraged him to start dating again after he broke up with his second serious girlfriend six months ago. “The reason it ended was I wasn’t really sure of who I was as a person and my personal boundaries that I could take in a relationship,” he explained. COVID-19 was a barrier to carefree dating these days, but he took it upon himself to get tested before dates and err on the side of transparency, to be considerate to the women he was meeting.

Jennifer and Jeff had been talking on Hinge for a few weeks and had already deepened some of their conversations past the usual superficial small talk, exchanging stories about their upbringing, overlapping traumas, therapy, and their relationship to their parents, when it occurred to Jennifer that he seemed like the right guy to try taking to couples therapy. Jeff had an innate vulnerability that she knew was needed for this specific date. So she popped a twofold question:

“Would you go on a first date with me, and would you want to try this whole couples therapy thing together?”

Jeff agreed. While it was a strange request, he found himself genuinely opening up to Jennifer on a deep level. She made it easy to say yes, he explained. “I wouldn’t have said yes to anyone, but Jen was someone I thought it would be a very invigorating experience [to do this with],” he said. “I thought it was worth the risk to do it.” 

They had a long, ambling first date in Manhattan, starting at a coffee shop and then moving over to the Guggenheim. “The dialogue between us, it was really easy,” Jeff said. “We didn’t disagree about much, and I definitely wanted to go on a second date with her.”

SCOTT & DANIELLE, THE HONEYMOONERS

Danielle, a funny and warm-hearted 25-year-old nurse in Seattle, had been single for six months and was dreading getting back on dating apps. They felt impersonal, and she felt no rush to meet someone new anyways. Her last relationship had been codependent, she explained, and she was actively working on herself in therapy—including recognizing how she tends to play the caretaker role in relationships. She was okay with taking her time before getting into another one.

Scott, a 29-year-old music librarian, had also just gotten out of a serious relationship—one that he describes as one of the best relationships he’s had so far. They ended things after nearly two years because she wanted to be a parent, and he wasn’t so sure. He knew it had to end: “If you actually love and admire someone, you want them to do all of their things [that they want to do].”

After a self-imposed romantic exile, he was casually dating again. Sharp-witted, handsome, and emotionally honest, Scott easily connected with others. The problem was wanting to stay. “I really love being alone,” he explained. “It would need to be a very unique sort of investment for me to look at something that was obviously failing and choose to stay and fix it, rather than to go back to this thing that I deeply love and am immensely comfortable with, which is being by myself.”

After matching on an app, Danielle and Scott had immediate virtual chemistry. When they finally decided to meet up for drinks on a Saturday afternoon, they both felt nervous about whether the attraction would hold up IRL. It did. “I was just as attracted to him, and also I was just comfortable,” she explained. “It just felt like we were just old friends, and we were just shooting the shit.” She was attracted to Scott’s intrinsic kindness and how supportive he seemed of his friends and family. She kept seeing positives that made her want to get to know Scott more. 

Scott, meanwhile, was as close to head-over-heels as it gets:

“I am freaking out, she’s so good.”

“She’s raucously funny, really disarmingly fast and funny. Her humor has a pretty horrifying vulgar streak to it that charms the pants off me.”

NANCY & ANLEE, THE NEWBIES

The longest relationship Nancy had ever been in lasted about two months. So all dating was still basically new territory to the 25-year-old writer, despite the fact that she self-identifies as a hopeless romantic. “I’ve never felt very understood deeply,” she admitted. Although bright and animated to be around, she was the type of person who loved asking about other people’s lives and hated talking about herself. She knew vulnerability was important—she’d recently started therapy for the first time, which she was excited about—but it just took a while for her.

Anlee, on the other hand, was married. The 26-year-old non-binary New Yorker had tied the knot with her primary partner last year, though they had recently opened their marriage after Anlee realized she wanted to experience other things as well. But she’d been a little slow to dive into dating, in part because she was generally a bit of an introvert and tended to get overwhelmed talking to a lot of people at once. Her partner was also the first person she ever dated, so funnily enough, the whole dating thing felt almost as new to Anlee as it did to Nancy.

The two met on Lex, a queer social and dating app. Nancy had posted an ad looking for people to watch movies with virtually, and Anlee took her up on the offer. The two watched Jennifer’s Body together and then spent hours talking late into the night—an experience that felt deeply meaningful and intimate to Anlee.

She was so giddy she couldn’t sleep that night. 

When they finally met up in person to hang out in Chinatown together, things were a little trickier because of the masks and social distancing. “If I'm being honest, it felt more like a friend date,” Anlee admitted. “I mean, she’s super cute, and she was dolled up and did her makeup and her hair. … I considered trying to hold hands under the context of it being cold, but then she wasn't really… like, she didn't have them out on the table.”

BIANCA & GABRIEL, THE VALUE SEEKERS

Bianca, a 26-year-old artist living in New Jersey, had been in exactly one serious relationship in the past, which was over five years ago. Back then, she wasn’t grounded by a strong sense of self. But after going on plenty of dates—good and bad—over the years, she had a much better understanding of what she wanted. Communication skills, a passion for creativity, and strong morals were top of the list.

Gabriel, a 34-year-old musician, started dating seriously in his mid-twenties and was in his last long-term relationship two years ago. As someone with a strong sense of integrity and purpose, he noticed it was difficult connecting about values and understanding what people really believe in the typical get-to-know-you stage.

“It has to come out more, I think, just over time with specific discussions or specific experiences that you’ll share together. It can be easy to agree with a lot of things on paper, but I think seeing that in action is very different.” 

When Bianca and Gabriel connected on OkCupid, they immediately started chatting about things like creativity, capitalism, and rest. “These are all really meaningful conversations to me and things that I already think about,” Bianca said. She realized he was pretty open-minded, so she decided to pop the question about attending couples therapy together within hours of meeting him. The session, by that point, was the next day. 

“It was pretty off the cuff,” Gabriel said with slight amusement. “I just felt super down. The concept intrigued me, but also, she intrigued me.”