What I Wish I Knew Before Online Dating At 20 (Actionable Guide)

What I Wish I Knew Before Online Dating At 20 (Actionable Guide)
Photo by Pratik Gupta / Unsplash

"Hey, I don't think it's going to work out."

This was the one-sentence text I received the next day after what I thought was an incredible 3+ hour date. We had dinner at a nice Korean restaurant, jumped on toy ladybug balls, and gazed at the stars. I was already fantasizing about what it would be like to have them as a girlfriend (naughty me). 

But, In one sentence, it was completely invalidated.

I didn't know whether to feel sad, angry, confused, or a combination of everything. In the end, I felt the standard experience with online dating: disappointment.

Throughout my six-month online dating adventure, I experienced ghosting, canceling dates an hour prior, and texting convos that could make a four-year-old's English essay look like Shakespearean literature. I’ve gone on 15+ dates, and finally have found a relationship.

But I’m completely burned out. 

Every date I went on I gave some of my soul to, and each time it didn’t work out, that part of me lingered on, cut in two. Some of the dates were great, I won't lie. And I learned A TON about myself and dating in the process. 

Here's the most important thing I learned: the apps are designed to make you fail.

The mindsets the apps instill in you about dating are counterproductive to actually forming a romantic relationship. It's not solely your fault if you are struggling with online dating--the odds are against you. I had a girlfriend for nine months before using the apps--I'm not an incel (I do play Dungeons And Dragons, but I promise). While it might not be your fault, it’s your responsibility to figure out how to use the apps more mindfully nonetheless.

Thankfully, I'm here to give you the actionable insightful guide to online dating I wish I had known before online dating at 20. This includes why you should be dating, how to choose an app, how to create your profile, how to set up and have a date, and the mindsets you should have throughout the entire process. 

And AaaAAaaaWWWwwwAAaaYYyyY we go!

The Apps Are Designed To Make You Fail--Here’s How You Succeed

The apps sell you a promise that lies on a false assumption. 

Here's the promise (make sure to read it as if it were in an Australian accent because it makes it funnier): "hey do you want to find a romantic partner but are tired of all the dates you have to go on only to realize, woops, they don't want kids, guess that was a waste of time? Well, booohhheee, we got just the thing for you. With online dating apps, you can put in what you're looking for upfront so we can match you with the people who are perfect for you. Plus, you can do all of it behind the comfort of your screen. You can find the perfect person, in less dates!"

Here's the problem with this promise: it assumes relationships are discovered, not made.

But that's not how relationships work. Take a look at your journey of self to understand why. Are you the same now as you were five years ago? Will you be the same in five years?

Clearly, it's wrong to think of relationships as A relationship in the first place. 

We, and therefore, our relationships are constantly evolving.

To deal with change in a partner, you must be open-minded, curious, able to navigate conflict, kind, and interested in aligning your life paths. Otherwise, your partner will change, and you will be unable to accept the “new them.” 

Do any of the things mentioned above get assessed through online dating profiles?


Dating apps ask you about your interests, your height, your religion, and your star sign (<-- WTF!). Everything that doesn’t matter that much for a long-term thriving relationship. 

My parents couldn't be farther apart based on the metrics these dating apps assess. My dad is a Swedish American Russian Literature Professor into woodworking, birdwatching, hunting, and camping. My mom is a Dutch Biology and Chemistry high school teacher who is about as literary-minded as a ten-year-old TikTokker. 

And yet, they have an incredible relationship.

So, now that we understand the false promise of online dating apps, how can we use the apps more mindfully?

Pick Your App And Design Your Profile Mindfully

If you're reading this article, I’m going to assume you have one goal and one goal only: you want to create a long-term thriving romantic relationship.

With that goal in mind, which app should you use? I can only give my rankings on three apps as these are the ones I used:

  1. Hinge: in my opinion the best online dating app by far. You have the most room for creating your profile mindfully. And you are incentivized to ask someone a question when matching with them to start a convo. And it's created by the author of the fantastic dating book, How Not To Die Alone.
  2. Bumble: a decent second to Hinge but you have to pay to send questions as convo starters which is free on Hinge...
  3. Tinder: use this if you want to gouge your eyes out. Prepare for your hopes to be used as tinder and go up in flames. 

Once you've picked your app, the next step is to create an awesome profile. There are tons of great articles on creating a good profile in terms of choosing pictures, prompts, etc, so I'm not going to write about that here. Check out this one if you want to.

But I'm going to give you a mindset that will be helpful: just like you design your social media feeds for the content you want to consume, design your profile to filter for the great potential partner you want to meet. 

I'm NOT saying you should be super picky in your design. What I recommend is that you define three of your non-negotiables in a relationship—things that you know you absolutely need (you might not have any)—and create your profile to filter for that.

Personally, my non-negotiables are:

  1. I NEED someone who is curious and open-minded. If I'm going to have 10,000 meals with them, I need to make sure it’s not my brain I want to eat out of boredom.
  2. I NEED someone outdoorsy and physically active (even if they like the city).
  3. I NEED someone who's just kind. You would be surprised how hard that is. Not kindness on the outside. Kindness on the inside, shown even outside the date.

My Hinge profile had a question that went "tell me about an awesome book or movie you have read recently and why you liked it!" This filtered for curious individuals.

I had tons of photos of me in the outdoors filtering for people into physical activities. 

And kindness, was more of a vibe thing.

Non-negotiables being said, I want to make one point very clear: when you first start dating, you don't know what you want.

I thought I did. I had more lists than hours in Minecraft (a lot…). I wanted an American girl who was into tennis, small towns, dogs and had the same interests as me. But my first girlfriend was a Singaporean who loved music, the city, and climbing. And it was a great relationship because she was all of the things mentioned above. 

Be open-minded.

Create A System For Finding Matches

Once you have your profile set up, you’re ready to start finding matches.

Actually, no you’re not; you have to buy the premium subscription to your online dating app.

Gasp, no, not the $30-$80 per month to get the premium. Let me ask you a question: If you knew spending that much money would increase your chances of finding a great romantic relationship partner by 30%, would you do it? I thought so. It’s still up to you, but if you have the money, I strongly encourage you to do so. 

So you're ready to start finding matches.

When should you search?

Personally, my favorite times were ten minutes after lunch and fifteen minutes or so at night when people are most active. The important thing is you create a system for doing so. If you don't have a system, your brain will go crazy with the dopamine of matching and want to do it all the time.

What are you looking for?

Remember the non-negotiables you defined earlier? Look for those on their profile. Look for effort in their profile and general attraction. That's it. I wouldn't worry about religion, interests, or whatever. Remember, be open-minded.

If you do this for long enough--it might take a few days or even weeks, especially if you're a guy--you will start having some matches. And with matches comes conversation. 

How To Have Great Conversations On The Apps

I remember when I first started getting matches I was sitting in my dorm room exuberant. Wow! Another person with their own background, interests, an entire life. I wonder what awesome things we will tal—

“Hey, how r u?” 

I froze. I waited for them to say something else. And waited. And waited…

After a while I realized this is genuinely what they thought was a good opening to our convo. As I had more and more conversations, my soul was slowly crushed by interactions that had the depth of an inch-deep pond. 

Unfortunately, a lot of people put zero effort into their texting convos. 

But here’s the good news: you will be different. 

Instead of saying how you should talk, I think it’s better to elaborate on how you shouldn’t. 

It’s pretty simple: do the opposite of what most people do.

Don’t open with anything like “are you an angel, because you look like you fell from heaven.” Don’t open asking, “how are you?” Don’t ask them to share something super vulnerable when you haven’t even seen each other physically. 

Honestly, just treat the interaction like you were actually talking to them in person. 

Connect one of their interests to one of your interests, one of their interests to another one of their interests, and ask questions that will give you stories back like “how did you come to believe this?” What’s one of your favorite x stories? 

Prepare, people will ghost you. They will give short shitty responses back. They won’t ask questions.

You wouldn’t have wanted to go on a date with them anyway.

It’s up to you, but generally, I like to try to get their number after having 2-3 good texting conversations about something, which usually takes 3 to 5 days. Then I text them to go on a date (which we will discuss more in the next session). I try to leave my Fridays and weekends relatively free for potential dates I might set up during the week.

Don't talk to more than 3+ people at a time.

We like having choices but not too many choices. In one study by Jonathan D. et al 2017 the more matches people had at a time, the more overwhelmed they were in picking a date and the less satisfied they were with whoever they chose.[^2] It’s like having 20 peanut butter brands ot pick from vs. three. The more choices you have the more you can think, “ehhh, but maybe that one might have been better.”

Restricting yourself to three people at a time ensures you give the people you do talk to the attention and respect they deserve and that you don’t overwhelm yourself with choice. 

There’s one last point I want to make about online dating interactions. This is possibly the most important point of all.

Treat The Other Person Like A Human Being

To understand this point, let me tell you an absurd story.

The year was 1932. While Hitler was building his power in Europe to start World War II, another war was happening on the opposite side of the world.

Australia was fighting the Emus.

You know, those smaller, sillier looking Ostriches. Over the last few decades, they had been terrorizing farmers' crops in Western Australia. So the Australian government sent Major G.P.W. Meredith of the Royal Australian Artillery with a truck and a few thousand machine gun bullets to deal with the issue. How hard could it be? They're just birds.

Hard. Very hard.

The Emus turned "dodging bullets" into an Olympic sport. They jumped, ducked, and emu'd about. After just one month, Australia admitted defeat.

Why am I telling you about this absurd war in a piece about the problems with online dating?

It's because the Australians experienced the same problem insidious to online dating: abstracting away complexity.

Just as the Australians underestimated the cunning of emus by abstracting them as "dumb birds", online dating reduces complex individuals to Pokemon cards, losing their human essence in a sea of swipes. As explained in Metaphors We Live By by George Lakoff and Mark Johnson, the more abstract something is, the less emotional weight we attach to it.

This is why online dating can be hell for many people, including me.

Personality, values, and interests become foggy, unimportant characteristics. Instead, stats comprise someone's attractiveness, height, religion, etc. And just like Pokémon cards, people feel they must catch em all!

People swipe on 10, 20, 100 people in a single day. According to a 2024 survey by Cloudwards, 19% of online dating users have talked to 11+ people simultaneously. Because there are so many choices, they don't bother asking thoughtful questions or giving interesting answers but instead start a conversation with the dreaded "Hi, how are you?" Inevitably, they are unable to keep up with all the texting or get bored--going on a date is really hard--so they do the only thing they can think of:

They ghost...They ghost so much...

According to a 2023 article in the Thriving Center Of Psychology84% of Millennials and Gen Zs have been ghosted and 65% have ghosted themselves. It turns out that 67% of people who have been ghosted flip the switch and ghost someone else. If someone ghosts you, you think it's okay to ghost someone else. This is even though 69% of ghosters report feeling guilty for ghosting.

Ghosting sucks for both parties.

Over my years of online dating, I've been ghosted probably 100+ times at this point (you might say maybe you're a serial killer, but it's not just me. Trust me, I've talked to others). Other dehumanizing things have also happened. I've had a date cancel on me an hour before because she quote on quote "had more homework than expected." I’ve had an hour-long date to an ice cream store where the person ended it by walking to their class, looking at their watch, staring at me expectantly and saying in a monotone voice, “anything else?” 

And worst of all, I'm also at fault.

I've ghosted. I've canceled a date. I've told someone it wouldn't work in a short text message.

The abstractedness of online dating brings out the worst in all of us.

What's the solution?

If abstraction causes the problems, concreteness is the solution.

I can't believe I'm saying this because it sounds so obvious, but instead of seeing your online dates as Pokémon cards, treat them as living breathing human beings.

Whenever I'm using the apps, I imagine the person I'm texting is sitting in the room right next to me. I ask “what would I think, feel, or do if they said this to me? Would I like to be treated that way?” I don't try to catch everyone but only swipe if I think I would genuinely like to go on a date. I don't talk to more than 3+ people at once. If I go on a date and don't want to continue with the person, I don't tell them in one sentence. I tell them I had a good time, a few things I liked about them, and wish them good luck in the future.

It's amazing how much better this makes you feel while on the apps.

You still encounter heartless people all the time; that's inevitable. But your heart lightens. A weight lifts off your shoulders.

You'll notice when you find someone is doing the same. They don't give 5-word responses. They think of thoughtful questions.

Unlike the Australians, they don't treat you like you're "just a bird."

They treat you like a human.

If you hold this principle to your heart, I’m confident you will start going on dates like I did. And good news, the same thing applies when you actually go on the date: treat them like a human. But there are some important other things to keep in mind as well. 

The Date

I’m going to encourage you to step out of your comfort zone and not do a coffee date.

Your goal on the first date is threefold:

  • Have a human connection
  • Have a shared emotional experience 
  • See your vibe with them

It’s possible to have this done on a coffee date, but from experience, it’s harder. 

Find ways to spice things up.

My favorite dates have been when I've gone on an adventure—bouldering, jumping across Lady Bug bulbs for fun, or taking random turns in the suburbs of Cornell. These adventures develop emotional connection and emotional connection is one of the most important factors for developing a relationship with someone.

Warning, Psych Nerd coming out. In romantic contexts, we can misattribute fear, curiosity, or awe, as liking for our partner. In one study, men rated women as more attractive if they got their number on a rickety bridge than if they got it on a secure cobblestone one. But seeing people in different contexts isn’t only better for attraction… 

It also helps you just get to know them better.

People don’t have concrete selves that act the same across contexts. Selves are fluid, morphing depending on the environment, the people around them, and more. Seeing your date in different contexts helps you see their selves more truly.

So I encourage you to try and come up with a date idea that goes between at least three different contexts.

One of my favorite go-to dates was to do something active like Ping-Pong or tree climbing, then have dinner, and then take a walk and watch the stars. Simple yet elegant. 

What do you talk about?

On a first date, I try to have a good time and get a vibe for the other person. 

I look for an interest of theirs and connect it to an interest of mine in a unique way. On one date, I talked about the connection between music and writing. On another, neuroscience and psychology. And on one more anime and language learning. 

In addition to this, I connect one of their interests to another one of their interests or ask questions that might lead to stories. 

There’s one mindset that I think will be particularly helpful for you date: just go in looking for the human connection.

In my early dates, I went in with the mindset I was looking for a girlfriend.

I would screen my dates searching for signs of girlfriend material like a Terminator. Ironically, this made it impossible actually to connect with them in the moment. Then I talked with another friend in the dating scene who told me something that changed everything: just look for the human connection. 

That's what you want anyway right?

A girlfriend would be great, but at the end of the day, a great convo would just mean connecting deeply with someone. Share the moment with them; it might be the last time you ever do. Isn't that beautiful? Two souls meeting on a rock in space for an interaction that could lead to them spending the rest of their lives together. 

This IS NOT an interview. It's a time to have fun.

After The Date

After every single date, I go through a series of post-date eight questions I got from How Not To Die Alone by Logan Ury. 

  • What side of me did they bring out? 
  • What side of me did they bring out? 
  • How did my body feel during the date? Stiff, relaxed, or something in between? 
  • Do I feel more energized or de-energized than I did before the date? 
  • Is there something about them I’m curious about? 
  • Did they make me laugh? 
  • Did I feel heard? 
  • Did I feel attractive in their presence? 
  • Did I feel captivated, bored, or something in between?

Notice how these questions are positively framed. There’s a reason for that. It’s what I call the second date rule.

The second date rule states, unless something catastrophic happens—they tell you they want to have kids after five minutes—you should assume you will go on a second date with the person.

Remember how we discussed you don’t know what you want in a relationship? 

For this reason, I encourage you to go on the second date. Like a beautiful flower, some people take two dates to truly open up. Maybe they were anxious on the first one, aren’t you sometimes? Give them another chance.

Treat your dating like an experiment.

You’re a scientist, and each date you go on teaches you more about what you do and don’t want in a partner. 

If you have gone on 2+ dates and don’t think it will work out with the other person, send them a text telling them. Don’t ghost. And be nice, for goodness sake. Say something you liked about them and wish them good luck in the future. 

Treat them like a human.

The Abundance Mindset

Inevitably, after going on some dates, you will be rejected, or you might reject someone else.

This can be very discouraging and frustrating, which is a valid feeling. One of the mindsets that can help you navigate this is the abundance mindset.

When I first started dating, I had a scarcity mindset.

I was insecure. I'd only ever had one girlfriend in my life and wanted to find another. I was impatient. I got intensely frustrated every time a date didn’t follow through. I treated the girl as the only one in the universe, so when it didn't work out, I felt I would never find love.

Then I adopted an abundance mentality.

I realized there are millions of awesome women in the world. Who's to say the one I'm dating is the only? Paradoxically, when I started treating every girl as less special, I started having better dates. I didn't come to the dates as needy. I didn't need anything from them. 

I was just trying to have a great time. 

Don't Burn Yourself Out

To this day, online dating has led to the worst burnout I have ever had.

In less than two college semesters, I went on 15+ dates. Each one I gave a bit of my soul. Each time it didn’t work out, a part of me died. I was expecting to find love, so when I found text messages with “how r u?” it discouraged me greatly. 

I want you to avoid falling for the same trap. Here are a few things that would have helped me burn out less.

First, expand your time horizon.

An amusing conversation with a friend at a dining hall illustrates this.

He wanted to get into online dating, but he was scared about the time and emotional investment it would take. He heard about me going on 15+ dates and didn’t know if he could do it. Then I asked him a question that reframed everything.

"If you could find your dream partner after having fifteen shitty dates, would you do it?"

"Of course."

I looked at him with a smirk.

If you’re expecting to find a romantic partner in six months, think two years. Think a lifetime. It sounds crazy, but hard things take time, and dating is no different. 

Second, try to stick to 1-2 dates a week, no more.

You might want to come out of the block swinging. But every date you go on takes a lot of emotional investment. If you go on more than two in a week, you might not be able to give your full self to someone on the actual date.

Thirdly, have a set date when you will take some time to rest.

I didn’t have this at first and it made it feel as if I would be in the trenches of online dating forever. As soon as I set the beginning of Spring break as my last time to go on a date, a tremendous weight lifted from my shoulders. Now I had time to look forward to as a rest point.

I’m confident if you follow the principles talked about in this article, you will be significantly more likely to create a meaningful relationship. A good romantic relationship can grow you in ways school, books, or work never could. In the online dating scene full of pond-deep interactions, hookups, and ghosting, it can become easy to believe it will never happen.

Don’t lose faith.

Trust in the process.

Treat the other person as a human being.

If you want to learn even more about my online dating experiences and how you can better date yourself, check out my video on the topic.


[^1]: Lawson, H. M., & Leck, K. (2006). Dynamics of Internet Dating. Social Science Computer Review, 24(2), 189-208. https://doi.org/10.1177/0894439305283402 

[^2]: Jonathan D. D’Angelo & Catalina L. Toma (2017) There Are Plenty of Fish in the Sea: The Effects of Choice Overload and Reversibility on Online Daters’ Satisfaction With Selected Partners, Media Psychology, 20:1, 1-27, DOI: 10.1080/15213269.2015.1121827