No more bad first dates. 5 radical ideas for modern online dating

On finding agency in dating.

Hello from New York,

Over the past month, I joined Write of Passage, a writing bootcamp that advertised to help us “become a better writer”, but in reality, it gave me the courage to express my voice.

Yes, the topic of the newsletter (if you recall) will still largely be about architecture, learnings, and how the environment affects who we are (I think). But here, I want to leave room for personal musings.

Dating. It’s a topic I never had the courage to write about, so see it as my expression of self and my hope to connect with you.

If any of the below resonates, say hi via replying to this email directly, comment below, or send a DM.

I look forward to hearing from you ☕

Coco

No more bad first dates. 5 radical ideas for modern online dating

Like many, I came into the dating world with a lot of hope. Maybe that next swipe will be the life partner I have been searching for.

In this long process of over 100 first dates, I haven’t found success (yet). There were moments when I felt the Return on Investment of spending time on these apps was exhaustingly low; the countless hours spent felt like “wasted time.” There were moments when I wished to go back to the world of meet cute offline. 

Often I question, is it me or is it the apps? 

After all, when Sean Rad came up with Tinder many years ago, he did not have the goal of helping people find love in mind. When he scribbled, "What market would bring in a billion dollars in revenue,” he prioritized revenue.¹ The incentives of online dating apps are misaligned with the incentives of those of us out there looking for love.

While there are many ways the online dating experience can be improved—and I’ve outlined some ideas below, I believe that ultimately we have control over what we want to experience. By looking beyond the social norms and adopting agency, we have the power to bring more enjoyment, intention, and hope to the experience.

A few ideas:

1. A Dating Manifesto

Everyone comes to the dating world with a very specific intention. Yet, rarely do people express these very specific preferences in their dating profiles. Many profiles highlight a few photos, preference for pineapple on a pizza, and one word responses to prompts. While to some, the pineapple is a dealbreaker, to me the texts tell the most about who they are. Even the tone, the grammar, and the content they decided to highlight are a window into the state of mind they’re in and what they care about.

I wish there is a way to amplify this little paragraph.

My proposed solution:

Writing a dating manifesto—a 500-1,500 word essay that describes where we come from, how we like to spend time, what is it that we care about, where we are in life, and where we're headed. It must be driven by honesty and authenticity. Instead of the glamorized version seen on social media, it is a trailer into the realities of our lives.

By writing a dating manifesto, one can front-load the effort to avoid wasted time later. 

While dating profiles today reduce us, a dating manifesto expands us. By articulating our thoughts clearly and putting them out in the world, we can be mutually screened based on genuineness; in the vast sea of people swiping online, the like-minded will know to find us. How often have we felt that, through someone's writing, we just know that we can be friends?

Put in marketing terms, by putting forth our intention, we are more likely to find the right "target audience."

A dating manifesto not only highlights our hobbies, it is an expression of vulnerability, the core of what breeds love in the first place. Through gathering our likes and our truth and questioning why we’re here in the first place, we may even discover something about us we did not know before.

For those who prefer more creative forms of expression, the dating manifesto can be "written" in the form of a video. In this video, we hear your voice, we see how you carry yourself, and we get to peek into your life and find the excitement to learn more.

I’ve gotten many requests asking what this “dating manifesto” actually looks like in practice and guidelines on how to write one. Here is mine, plus a mini guideline.

2. Commitment to multiple dates (after a fine first date)

Many people are stuck in the cycle of being a “serial first dater.” 

In the world of online dating where thousands of prospects sit at our fingertips, people search for that “perfection.” It is not uncommon to see someone going on their 100th first date, while the conversion to a second date is appallingly low. And a good first date can be labeled as a “bad one” if it does not lead to another date.

I believe most of us value a genuine connection—be it a short one, one that lasts through a phase in our lives, or one that luckily lasts a lifetime. However, to achieve this connection, it requires a level of consistency and repeated exposure. We may feel that spark after a first date, but we cannot write off those who may find their way to surprise us later.²

When we prioritize breadth and quantity, we forgo depth and the beauty of digging deeper and getting to know someone even if this person may not be "perfect."

I propose an experiment: if we find attraction after a first date, we commit to a schedule of three more dates within that month.³

These dates are meant to be fun. Both parties take turns selecting activities they've always wanted to do, and the other will say yes to the activity proposed (within budget, without physical harm). This way, we give the other person a chance to help us realize our dreams over a shared experience.

In doing so, we become more aware of our tendencies to stop short, increase our chance of achieving that connection, and unveil a person that we did not expect.

3. Awareness of biological attraction

How often have we found someone who looked good in photos, but not at all what we expected in person?

Physical attraction is important. I’ll make a bold claim: the foundation of a lasting relationship is not personality (even though we like to believe it so), it's attraction.

However, it seems that we’re not so great at identifying who is attractive based on photos. I believe the answer lies in distinguishing between physical attraction and biological attraction. Physical attraction seems to be based on looks, a conscious judgment of whether someone is hot. Biological attraction, on the other hand, lies in our subconscious; it is vibrating on the same frequency; it is based on the actual chemistry, our genetic makeup, something we cannot quite explain with words.

If artificial intelligence or technology is meant to help, it should be in the form of biotech that takes chemistry into the algorithm. To step into the sci-fi yet not-so-distant future, perhaps onboarding would include a sweat sample analysis, measuring genetic makeup, pheromone levels, and therefore biological compatibility.⁴

Before we go that far, I find it helpful to be more attuned to the inexplicable, to feel more, think less. Maybe go for a walk with that date without a destination and see how that feels.

4. Feedback loop

Often after a first date, we are thrown into the black hole of not knowing how things went. Here, feedback is important. And whether or not there is mutual attraction or potential, there is always room for improvement.

The solution can be on the platform or the individual level.

On the platform level, dating apps can go beyond software technology to include service-level design, providing a service where the relationship between the platform and the users extends beyond the point of transaction.

For example, the app will not only make the initial connection but follow the participants through the initial journey. Matchmaking focuses on making the match (as the name implies), while this service focuses on helping individuals find success in the journey of dating.⁵ Perhaps, after a first date, an experienced love coach will give feedback after having a conversation with both parties. Through this conversation, we become more mindful of the things we have said and the things unsaid. 

We can apply this mentality on the individual level. After a date, we can reflect on how we could've done better, and move forward with clarity.

In career, and in life, we seek areas of improvement and growth. Similarly, dating is iterative. We cannot expect to act the same way on every first date and expect different results.

It is about applying the agency we find in other areas of our lives to dating.

5. Be unapologetically direct

How we grew up affects what we want in life. Through our upbringing and environment, we carry with us certain expectations along with the definition of what is normal.

I grew up in China. To an average Chinese person, people set very clear intentions when it comes to dating. On the first date, we hear a man say: "I plan to get married next year. And if you're not on the same page, let's not waste time." Dating apps in China accentuate this culture. In a typical dating profile, one lists their salary range, home ownership, and whether their mortgage is paid off on that home ownership.

The natural response in an American perhaps is elements of surprise, even cringe. We stand high on the moral pedestal: we marry for true love and not material goods.

Yet when we cringe, is it because it is wrong, less effective, or just not the norm?

Maybe we don’t have to go that far to learn from the Chinese. But in my experience, when someone is honest, knows what they truly want, and can express their wants confidently, it’s attractive. 

—

The last bonus point is leading with kindness.

It is easy to get into the rhythm of matching with a new date. Like fast fashion, the speed and ease of meeting someone new and the dopamine rush of a new prospect make it easy to treat each other as dispensable.

Some say the confounding factor that made their date experiences great is whether they’ve met in person. But I think that’s what our mind wants to tell us.

Ultimately, it is a choice.

Buddhism teaches the law of cause and effect. I learned that if we approach our dates with kindness, positivity, and vulnerability, we get the same in return. When a date doesn’t lead to anything, it doesn’t mean it was bad. I’m learning to treat each date as a unique experience of its own, to not come with defined goals or expectations, to shut the voices in my mind and make space to truly listen to the other, to go against the currents, and to simply, be kind. 

By doing so, I no longer see these dates as “wasted time.”

If there is one thing that the dating apps really helped, it is bringing together people with the same intention: dating. Instead of running away from it and going back to the world without technology, we can give it another shot, but with a refreshed frame of mind.

And hey, if you resonated with any of the ideas above, I muse about building a pilot service if there are volunteers—comment on this post :)

Special thanks to friends at Write of Passage whose comments have shaped this essay and give me the courage to speak from my heart. Truly grateful: Edgar Baum, Michaelangelo Caporale, Vidhika Bansal, Adam Siegel, Jake Ballinger, Alivia Duran, Jules Stefanich, Jean-Philippe Lejeune, Arjun Madgavkar, Jasmine Aug, Caleb Fallin, Albert Martinez, Genesis Dayrit, Aaliah Elnasseh, Natasha Lee, and Diana Monzón.

1. From a conversation with an early employee.

2. Through self-inquiry after reading the book Attached (highly recommend!), I started questioning if the spark was real. Lack of that “spark” may mean the other party is secure. While when I felt that “spark” it may have been my own anxiousness at play.

3. As for the how, maybe come up with a few fun ideas on things to do or places to go even before meeting up or during the first date. If a dating app can help on the platform level, it’d be great if they can help prompt this!

4. A related article from Fast Company: Dating Site to Match Couples Based on Smell

5. Providing additional services to ensure the success of the participants is seen in other types of tech companies. Andela, a Nigerian edtech startup that helps global companies source tech talent in Africa, didn't simply build a software-only marketplace that matches companies to talent; they created an entire end-to-end operation to train local engineers to become qualified for hire. From a conversation with Andela’s co-founder, Iyinoluwa Aboyeji.