Rewriting the Dating Script

In a dating culture where standards and expectations are gone, how does one find a real connection?
November 3, 2020 Updated: November 3, 2020

Clients come to Leila Tomasone with questions, failures, and just sheer confusion about their love lives.

“Dating—what does that word even mean?” asked Tomasone, a relationship coach and mother of two based in Virginia. As a matter of fact, dating hasn’t been around that long, she points out. Marriages used to be arranged, and courtship in modern history was a fairly transparent public affair. “Young men would call a young lady’s home and the family was there, and they’d pick up the phone and they’d want to know what’s up with this guy.”

The young ladies would go on these dates, but the expectations were typically that they were innocent (chaperoned even, going further back). “The standard for intimacy in a relationship was marriage,” Tomasone said. “It happened a lot faster, and it was understood that if a man took a young lady out for several dates, that ended up heading toward marriage or he was wasting her time.”

Relationships coach Leila Tomasone. (Courtesy of Leila Tomasone)

Those scripts, standards, and expectations are completely gone, but no new structure rose to replace it. Tomasone has talked to people who questioned what it even means to accept or ask someone out on a date, what obligations that entails, and whether their actions mirror their words. Foundational relationship questions, such as whether they were seeing other people, or where things were headed, were things people had no idea how to ask, or worse, just assumed.

Tomasone started giving her friends advice, and among her circle there was a positive ripple effect. Since then, she’s turned this skill into a coaching business.

The truth is, Tomasone said, it started with her own relationship problems.

“It started out with my experience having a bad marriage and then having some bad relationships and just needing to get myself sorted out,” Tomasone said. It was “trial by fire,” but through her path of errors, she picked up the psychology of relationships, as well as resources, skills, and strategies, and realized so many other people needed the same.

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The documentary “The Dating Project” follows five single people, ages 18 to 40, as they navigate the new dating landscape. (Courtesy of The Dating Project)

A Culture Without Dating

Tomasone’s experiences were far from uncommon, and not even close to extreme.

Boston College Professor Kerry Cronin made headlines a few years ago when she began her “dating project,” giving students a mandatory assignment where they had to ask someone out on a date. The emails she shares in her talks range from the comical to tragic—from a student who “felt like a goddess” after successfully asking someone to coffee and having scores of people tell her she was “so brave” because they’d heard about Cronin’s assignment, to a senior who originally professed to prefer hookup culture and didn’t want or need to date, and who four years later asked Cronin to “please fix” her.

Cronin added that it’s not actually that young people are having more sex, but that the “Netflix and chill” no-strings-attached culture of hooking up and hanging out was the dominant one. So much so that asking someone to coffee for a 60- to 90-minute date was utterly nerve-wracking for so many students—and high-achieving, accomplished, socially adept students, at that. They literally had no idea what dating was. The idea of getting to know someone, and in turn learning to reveal themselves, was an alien one.

So Cronin handed out rules (must ask in person, schedule for sometime in the next three days, etc.), and the seemingly bizarre and antiquated ritual went viral enough that the entire campus (and then some) have since heard of it. Asking or being asked on a date was less bizarre knowing that “it’s for that professor’s assignment.”

Professor Kerry Cronin of Boston College made headlines a few years ago when she gave students a mandatory assignment to ask someone out on a date. (Courtesy of The Dating Project)

On the opposite coast in California, filmmakers Megan Harrington and Catherine Fowler Sample were at a friend’s party, with over a dozen women in their 20s who were all single and not dating. It struck them as odd, and as they conceived of a documentary to look at the world of dating, broken as it is, for a range of people from ages 18 to 40, they encountered Cronin’s assignment—which they featured in their widely-viewed documentary “The Dating Project.”

Half of America is single, Harrington said, and there is a prevailing sense of loneliness, and being connected but feeling disconnected. There is also a feeling of being let down, from people who’ve digested movies, songs, TV shows, and articles about how to live the good single life; people are starting to articulate how the ideals depicted promise happiness and completeness, yet they aren’t finding it by following those scripts.

“It’s a lack of a real, authentic connection with someone,” Harrington said. She wasn’t a stranger to the traditional date, but people less than a decade her age on college campuses had no concept of the coffee date, and that was something they wanted to examine.

Megan Harrington wrote and produced the documentary “The Dating Project.” (Courtesy of The Dating Project)

As Cronin explained in the film, young people may not have been taught how to date, but the culture is speaking very, very loudly, and it’s teaching them hookup culture, and they might not even realize it.

Harrington said they asked a lot of questions people don’t normally think about during the documentary, and over and over people would realize what they watch and hear conditions their actions—like that pop song whose lyrics they’d never really listened to, even though they’d heard it a dozen times.

“We develop habits, and that’s the case for anything,” Harrington said. That “good single life” people have been conditioned to live is one where relationships are transactional, where people are used, and these habits become ingrained.

With the film and the dating assignment, the producers aimed to show “something that’s more realistic, something more in line with what people’s hearts are yearning for, which is relationship and true connection,” Harrington said. “Not the superficial and not the transactional, not the immediate and physical.”

These habits spill over from the college campuses, Fowler Sample said. She realized during the making of the documentary that 40-year-olds were trapped in the same habits and pitfalls that the college students were in.

In addition to producing “The Dating Project,” Catherine Fowler Sample has also written two curriculum series focused on building healthy dating relationships and marriages. Incidentally, while producing the documentary, she started dating the man who would become her husband. (Courtesy of The Dating Project)

“This is really a crisis of a huge nature in our culture that needs to be explained and explored,” she said. As she was producing the film and seeing audience reactions to the five people they were following on their dating journeys, and as she heard questions and discussions after screenings, to even a recent doctor’s appointment when her obstetrician mentioned showing “The Dating Project” to teenagers without knowing her connection to the film, Fowler Sample saw what a huge ripple effect this issue has.

Dating is a lighthearted subject, but it certainly isn’t a trivial one, she realized.

“It really is one of the deepest subjects, and it’s something that is impacting, quite frankly, the next generations and generations to come if we can’t correct what we’re doing now,” she said. “It’s almost like the heart of what keeps the world going, it’s the start of it. If nobody was dating, then nobody would be getting married, and then the world wouldn’t continue.”

It’s also at the heart of the loneliness crisis, as Fowler Sample said. Without that dating script, young people had no idea how to get to know other people or how to connect. People would “talk” forever on dating apps but never go anywhere, and never make that real connection. Oversexualizing dating and making it about the physical so quickly had muddled the script.

“What I do know and have seen time and time again is that despite this confusion, everybody does want the happy, wholesome relationship. They want that coffee date. They want to connect with someone in a real way,” Fowler Sample said. Her hope is that the film helps bring back casual dating, which really should be an innocent middle ground between this hookup culture and life commitment. The wedding bells shouldn’t go off when you ask someone on a coffee date, but that person should be worth treating with human dignity and consideration, she said, which runs counter to the transactional nature of hookup culture, where people get ghosted all the time.

“It makes total sense for people to be so confused, because there hasn’t been any direction, and people want that direction. That was another surprise of the project,” Fowler Sample said. “By and large, people want direction.”

A Culture Without Communication

People haven’t just forgotten how to ask each other out on dates, they’ve forgotten how to communicate in relationships more generally, Tomasone found. Most often, people sleep together right off the bat and never get around to talking about what their relationship is and where it’s going. The two people involved may have completely different ideas about what their relationship is to each other.

“There are assumptions that people bring into dating,” Tomasone said. It’s easy for people to say that they don’t assume there are any obligations when they go out on a date, but the reality is that everyone she talks to feels there are obligations, pushed from the culture.

“It takes a lot of confidence to shed cultural expectations and just say this is what I want, this is what I can offer, take it or leave it, and it’s really putting ourselves out there, to someone who will ‘leave it.’ That’s really hard, too,” Tomasone said. People might feel like there’s an obligation to be intimate quickly into the relationship, or assume that they’re exclusive and the person they’re seeing isn’t seeing anyone else.

With no rules, expectations vary wildly, and two people with completely different assumptions might stay with each other, or “hang out,” for years, each with different mental pictures of what the relationship is and where it’s heading.

In fact, assumptions are so ingrained that many people aren’t even consciously thinking about what they want out of dating; sometimes they’re surprised when Tomasone asks. There’s a moment of epiphany, where they say, “Oh, I can ask for what I want.”


The Rise of Relationship Coaching

For people who’ve been dating without rules for years, setting those standards is easier said than done. The biggest thing Tomasone is asked is how to assert themselves in setting the standards they want to have, and whether they have any right to insist on dating this way.

If the current culture is that people go on two dates, assume exclusivity and monogamy, and hang out with no idea where the relationship is going or if or when marriage will ever enter the picture, there’s a lot of working backward that people do when they first start dating with purpose, Tomasone said. They have to first think about what they want out of dating.

Most of these dating clients have marriage and family in mind, and if they’re going back to a pre-hook-up dating culture, they’ll be dating many people, but also be decisive about whether the person is the one for them or not (parenting expert Kari Kampakis has noted, “Dating is really about rejection.”). If they’re dating with a purpose in mind, they also consciously think about whether their values align and discuss these things.

Tomasone tells women especially to not quickly become exclusive; to let the people they’re dating know, and in fact let the man lead the pace of the relationship and be the one to escalate the relationship status to exclusivity.

(Priscilla Du Preez/Unsplash)

“If he needs to ask her for exclusivity, then it’s not presumed until that happens,” Tomasone said. It’s not about knowing, it’s about doing, she added. “Part of learning is to go through the physical steps. You can say, ‘I want to have high standards,’ well, you need to practice having high standards, and act through that before you’ll actually feel it in your core.”

Tomasone coaches married couples as well as dating singles, and what she’s learned is that these issues of communication are ones that follow people into marriage.

If people are constantly assuming what their spouse wants or thinks instead of openly discussing these things, they might think they’re smoothing things over when they explain away something in their minds. “That’s like erasing yourself and your own perspective from the relationship, and how can you have a relationship if you’re erasing yourself from it?” she said. In reality, what they now have is an unhealthy codependent relationship.

“The dating advice is so helpful because it’s all the things they need to know to have a great relationship going forward,” Tomasone said. “You have to keep up with [the communication] and not let it fall by the wayside.”