A little over a year ago, I wrote a popular piece for Vox on “How Swiping Ruined Online Dating” and subsequently deleted all of my seven dating apps. I wasn’t new to online dating; I had been on sites and apps since 2009, longer than most of my peers. By 2016, I was proverbially spent — as apps became more widespread, they were taking too much of my time and attention. I saw problems with their design, and further, disliked how they were shifting dating culture. Nothing about dating through apps was mindful anymore. Truthfully, I was no longer learning enough about relationships or even love in a healthy manner either. Isn’t that the point of dating — to have fun, learn, grow, and love?

I didn’t want to stop dating altogether. Rather, I decided to take an approach I was familiar with from my career: asking others for advice and for introductions. I sent an email to 700 people, asking to get set up. To me, asking my network to set me up meant a potentially better use of my time and attention. I was curious to see who I would meet, and how people would respond to such a non-traditional request. Could doing something vulnerable but also bold lead to a better result than apps had led me to thus far?

The email was too long to share here, but went a little something like this:


I’m 30. I’ve been doing some reflecting and work on myself over the last few years. I’m feeling pretty great about my career, and love the home and community I’ve built. But I’ve decided to ask for some help in the dating and love department. This is an email asking you to set me up.

Since I started my career as an indie music blogger, I made a Spotify playlist of modern love songs so you have something to listen to to get inspired (like Real Love Baby by Father John Misty, FVR by Janelle Kroll, Can’t Do Without You by Caribou, and some throwbacks like Thinking of You by Sister Sledge).

Though I’ve been an equal-opportunity dater on apps for the last eight years, I’ve now determined that I’m into/or would like to be into curious, kind, charismatic, and generally healthy dudes. Think artsy and creative, not bros (this is a historical rather than aspirational fact). Added bonus for loving both New York and Los Angeles, and liking to travel internationally. If they’re close with their friends, I’ll be even happier — community matters to me, as you know.

I then quoted philosopher and author Alain de Botton: “A good partnership is not so much one between two healthy people (there aren’t many of these on the planet), it’s one between two demented people who have had the skill or luck to find a non-threatening conscious accommodation between their relative insanities.” And I subsequently spelled out some of my own idiosyncrasies — like how direct I can be, or how long it can take for me to emotionally open up.

I closed with a Pinterest “Dudeboard” (rather than a mood board) to show the types of men I am attracted to, and also, to elicit some humor and levity. It’s full of facial hair, fitted jeans, and sly or goofy smiles to this day. The best feedback I got on the dudeboard specifically was, “Isn’t this a little aspirational?” My response: why yes, that’s what mood and vision boards are for.

The unapologetically aspirational “dudeboard”: yes to creative types and facial hair, no to bros

The note was a mixture of serious but also irreverent, to mirror my personality, but also because I couldn’t write it any other way; I had never received a note like it, so I felt like I was entering new, uncharted waters.

Why 700 people? Because I had read a Stanford University paper from 1973 talking about The Strength of Weak Ties. It posited that it’s in fact the acquaintances in our lives that make the most difference — when it comes to business, and even when it comes to meeting other people.

The response was overwhelming. Some people congratulated me on my courage, sending notes about their experiences and their philosophy on love. Others sent notes decrying my technique, telling me “desiring outcomes only leads to suffering.” A friend I appreciate and respect told me in person that “he loved me but if I tried so hard, I’d never find what I was looking for.”

Six people set me up on dates. The people who set me up were not my best friends; they were the acquaintances I felt a little awkward sending such a personal note to (in other words, props to the Strength of Weak Ties theory). I ended up dating the seventh man I met through friends for a half year. As we were ending our relationship, I sent him the email, since we had spoken of it, but he hadn’t seen it. During our (fairly healthy) break up conversation, he ultimately noted that had he seen the email when we met, he would have known I wasn’t ready to date.

Was it uncomfortable to send that email and wait for the replies to roll in? Absolutely.

Do I regret sending it? Absolutely not.

How we talk (or don’t talk) about love

Though I didn’t know it at the time, my email, sent in October 2016, and everything that followed, expressed something that’s become clearer to me since: I’m not alone in my dissatisfaction of navigating the murky waters of dating or exploring love, especially in a tumultuous political time. Because in America, while we’re slowly making progress in how we talk about gender, workplace dynamics, and sex — especially in the last few months — we still have almost no idea how to talk about love.

We keep our thoughts and experiences with dating and love mostly to ourselves or to our (biased) innermost community, family and friends, making it hard to evolve our thinking or to change our behavior. And in doing so, we unknowingly prevent a healthy conversation about how the nature of love — how we find and cultivate and experience it — is changing, and how our behavior may need to change too.

I don’t believe we can have complete conversations and bring about positive change when it comes to gender, workplace dynamics, or sex in America without also talking more openly about love.

Asking for what we want in love versus in the workplace

If I had sent a similar email detailing my job search — sharing my professional attributes, history, accomplishments, and aspirations, with examples of ideal jobs — the response would have been markedly different. No one (I hope) would have told me to stop trying so hard, or that I was aiming too high.

I wondered: why do we approach work with such a deliberate effort in this country, yet we treat love and the pursuit of partnership so dramatically differently? Why do we use active language in the workplace, like “go for it!” “Reach out for informational interviews,” and “Don’t be afraid to be clear about your goals and ask for what you want,” while we use passive language when it comes to love: “don’t try so hard, you won’t find what you’re looking for,” or “let it happen,” or “if you’re so specific about what you want, you won’t ever be happy”? Can we achieve what we want in our careers and in love with such a different approach?

And in today’s world, where the personal and professional feel inextricably intertwined, why can’t we bring the same active approach to love that we bring to the job search?

Dr. Jordana Jacobs, a psychotherapist with her PhD in clinical psychology who has spent years researching love, told me , “Maybe it’s possible to separate these aspects of our lives, but should we? No. Love takes hard work. And to delude ourselves into thinking otherwise is extremely detrimental because then the moment it inevitably does get hard, we disengage.”

“Love takes hard work,” says psychotherapist Jordana Jacobs. “And to delude ourselves into thinking otherwise is extremely detrimental.”

That’s why Jacobs and her co-founder Kate Deibler created lovewise, a 6-week course to help prepare couples (sorry, single folks) for how to maintain and sustain love in long-term partnerships. Lovewise is, in part, a response to the expectations created by our app-saturated dating world — the same world that prompted my email blast.

“With online dating offering endless romantic alternatives, we are seduced into believing that there is someone with whom love will be easy with out there waiting for us,” Jacobs said. “This is simply not true.”

The problem with love in America

In America, we don’t talk very seriously, healthily, or substantively about love. Sure, we make movies and television shows, write songs, and sometimes people write books or poems about it. But for the most part, the topic is left to our parents and to conversations with friends (if we’re lucky). I’m positive many Americans have never had an explicit, honest, open, or even informed conversation about the meaning or feeling of love.

Jacobs agrees, noting that movies, television shows, and songs can often be “detrimental to our perception of love,” only capturing extremes and failing to depict the more often lived-in, in-between, or gray area. “Psychologists, philosophers, and anthropologists cite different reasons, but most agree on one simple fact: We’re unprepared. That is, in a society where we plan for everything, from heavily researching brunch spots to googling future employers, we cross our fingers that, in love, we can just…wing it.”

To complicate matters, unlike in most areas of our lives, we don’t have a curriculum or school for love, though choosing a partner is one of the most impactful decisions we make.

In her book All About Love: New Visions, acclaimed author bell hooks eloquently articulates this: “Schools for love do not exist. Everyone assumes that we will know how to love instinctively. Despite overwhelming evidence to the contrary, we still accept that the family is the primary school for love. Those of us who do not learn how to love among family are expected to experience love in romantic relationships. However this love often eludes us.”

Not all of us can take Dr. Meg Poe’s class on love, entitled Love Actually, at NYU, after all. Instead, we find ourselves educating ourselves from popular media or from our uneven experiences with our families. For people of a certain generation and demographic, the game plan looks something like this: We enter the world, stumble through youthful romances, join dating apps, engage with people at bars and in the workplace, all with our own not-always-overlapping understandings of love, romance, friendship, and dating. No wonder we’re behaving badly; we don’t even know or share a common language and baseline for normal. As Alain de Botton, the philosopher and creator of School of Life, writes in The Course of Love, “Love is a skill, not just an enthusiasm.”

If we’re not equipping ourselves with an understanding of skillful love — romantic and non-romantic, and how our quest for it shapes and forms us — how do we expect to treat each other with respect, whether in the workplace or in the bedroom?

Now is the time: where #MeToo plays into the conversation

A wise man once wrote that “Your most casual encounter could lead to something bigger, so treat those interactions with that level of respect.” That sound advice comes from none other than Aziz Ansari in his best-selling book, Modern Romance. Yet the events of the last few months have brought to light just how few people, including Ansari himself, have treated their every encounter with that very respect.

Whether in the workplace or in the bedroom, we’re now seeing a social and cultural upheaval across industries and genders as a light is shone on inequities rooted, ultimately, in a disconcerting lack of respect.

Though it has been incredible to see deeper conversations about the workplace dynamic and more lately, sex, emerge and develop, it’s also made for a complicated few months. Scores of women from different fields have stepped up to out their harassers and confront perpetrators of assault and coercion, feeling for the first time that “time’s up.” Empowered by a rising wave of evolved feminism and feminists (and their allies), supported through ongoing media conversations, and in response to recent blows to women’s rights at the federal and state levels, there is a rising tide of momentum.

In the last few months, we’ve found ourselves getting more comfortable talking about sex. In piece after piece, writers have broached complicated topics and started a flurry of important reflection and analysis.

#MeToo opened the door that led to this; sure it’s messy, but it’s progress.

But it’s more than #MeToo. These topics have come up because of a certain tendency to avoid talking about gender, sex, and loving relationships in America in a meaningful, authentic, and healthy manner. It’s why I had the types of responses to my email I had. It’s why talking about gender in the workplace and why talking about sex feels messy and uncomfortable. Everything is connected.

The author, in Los Angeles.

Toward a new normal

In a world where the dating landscape is changing so rapidly, and where norms are barely established within one generation, let alone cross-generation, we need to have more conversations. We need to have awkward conversations. We need to get comfortable talking about dating, the struggles, the wins, and the nuance. We need to get comfortable doing the hard work.

We also need to educate more people on what workforce dynamics should be like, what open, honest, consensual sex should and could be like, and we need to hold space for people to ask more questions. None of this is black and white.

And then, we need to get really comfortable talking about love with those near to us, and what we want from it. I would hope that in the near future, my email experiment would lose any sense of stigma; after all, many civilizations throughout history have had matchmakers.

Even if you make a similar choice like I made, to go “appstinent” as my smart friend so aptly named it, you may not be able to fully escape digital dating. Mark Zuckerberg’s announcement that Facebook is getting into dating only two days ago sent Match Group’s stock plummeting (the owner of Tinder and OkCupid). Only time will tell whether the feature lasts, but Facebook will soon orient itself toward “real, long-term relationships.” After all, no matter how frustrating it can be, dating is a lucrative space. 

So I find myself thinking about Aziz Ansari again. I can’t avoid it. He’s one of the few dominating popular culture who had the courage and vulnerability to start and lead a conversation about love in today’s world. As an acutely smart and observant friend said to me recently, “it feels like we’re refereeing a game whose rules we don’t even know or acknowledge.” What kind of game is this then? Would you play in such a match?

But the other part of it, at least for me, is this: if we as a culture and the media and society decide to referee as we have, then who will have the courage to continue the conversation? Who will not cower from the internet and from popular culture in fear of making a mistake, small or large? What kind of world will we live in if we are all walking on eggshells that turn into glass, even under our best of romantic intentions?

Surely not one where we can learn to “stand in love,” as Erich Fromm wrote in his seminal book, The Art of Loving. “Love is not primarily a relationship to a specific person; it is an attitude, an orientation of character which determines the relatedness of a person to the world as a whole, not toward one ‘object’ of love.”

For this, I am a hopeful romantic.