What I Learned From Going on 100+ First Dates Before Meeting My Soulmate

30 evidence-based lessons on finding true love

Sep 15, 2020

I went on over 100 first dates before I met my wife.

I tried dating services from Match, OkCupid, Hinge, Coffee Meets Bagel, Bumble, Tinder, The League, Happn, eHarmony, Plenty of Fish, Jdate, Yahoo Personals, Three Day Rule, and speed dating (once).

During my dating journey, I met some exceptional women and had some wonderful relationships. But none of them felt quite right. Somewhere along the way, I decided I wasn’t going to settle. I was going to find the perfect person for me.

When I finally met my wife, I was in my mid-30’s, active on eight different dating apps, and going on 2–5 dates every week.

I’ve had some time to reflect on what I learned along the way, which boiled down to these 30 lessons on dating, love, and life, as evidenced by my own experience.

1. Know who you are and what you bring to the table.

Understanding your own strengths, weaknesses, preferences, and personality traits will help you find the right partner. Half the challenge of falling in love is finding the person who thinks you’re perfect just the way you are.

It took a while for me to accept it, but I’ll never be the tall, dark, and handsome type. I’m not fun-loving, adventurous, spontaneous, or exciting. I can’t light up a room or impress a crowd with a hilarious joke.

However, I’m pretty smart and successful. I have high emotional intelligence and strong communication skills. I’m a great listener, a loyal and attentive partner, and a highly reliable person.

Once I developed an honest sense of who I was and what I offered, it was much easier to find women who valued the things that make me who I am.

I found personality tests, such as the Myers-Briggs Type Indicator, to be a huge help in understanding myself. I also read a great book on dating, Why Him? Why Her? (affiliate link), which helped me focus on my strengths.

Understanding who you are will not only give you deeper self-knowledge, it’ll help you find a partner who’s buying exactly what you’re selling.

2. Create a list for your dream partner.

Think about the important things you’re looking for in an ideal partner and write them all down as a list. What do they look like physically? What are their biggest strengths? How do they spend their free time? What do they do for work? Passions? Education? Family? Location?

The longer and more detailed your list, the better you know yourself. If your list is too short and too vague, it’s a sign you don’t really know what you want.

A long list is good not because it has so many requirements, but because it has rich and passionate details about the things you’re looking for. But be careful not to make it so long and detailed that you’re describing someone who likely doesn’t exist.

For example, it’s better to have five details about your ideal partner’s intense passion for the arts than list five different complex skills he’s mastered. The first says, “I clearly need a partner who cares about the arts as much as I do.” The second says, “I want an impossible superman.”

Paint a complete picture of what you’re looking for in a partner, but focus on the important stuff and be flexible on the rest.

Your list will act as your map and compass on your dating journey. It’ll focus your energy on people that are a good fit, and will give you the confidence you’re headed in the right direction.

Once I wrote my list, it really focused my dating. I went on fewer dates and they all started to feel like the right type of person for me. My list gave me the confidence to say, “This is what I want and I’m getting close.”

3. Be honest: How picky are you?

When it comes to love, we’re all kind of picky. I mean, who wants to settle?

There’s nothing wrong with being picky when looking for your partner. But, keep in mind that the more particular you are, the more time and effort it will take to find your special someone.

Somewhere along the way, I realized I was pretty picky. So I prepared myself emotionally that it could take a while. In the end, I didn’t meet my wife until my mid-30s, after going on over 100 first dates. Interestingly, she turned out to be an INFJ, which is one of the rarest Myers-Briggs personality types, representing less than 1% of the total population.

Here are two quick litmus tests for how picky you are:

Think about your ideal partner: How often do you see someone matching that description in your world?
Look at your personal life: Are you close with many different people, or do you have a small group of carefully picked friends?

There’s no right or wrong level of pickiness. It’s a personal choice. Just be honest about how picky you really are.

4) Get your stuff together and become the best version of you.

We all have baggage, bad habits, hangups, and stuff we’re working through. That’s an ongoing part of life. Now is the perfect time to address your issues so they don’t disrupt your future relationships.

I once went on a first date with a brilliant woman who clearly had an unhealthy relationship with money. I decided to steer clear. Similarly, I watched a good friend with a drinking problem chase away a series of promising girlfriends.

I’ll never forget the disgusted look on my date’s face when I stumbled into a coffee shop 10 minutes late, red-faced and out of breath, with mud and snow spattered all over my rumpled pants. It was a wake-up call that I needed to get my stressful career under control.

Don’t let your baggage be a red flag in your next relationship. Work on becoming the best version of yourself today, so that when the right person comes along, you’re ready.

5. Find the right dating channel for you.

There are many places to meet new people: work, school, worship, volunteering, clubs, bars, parties, dating apps, and more.

The key is to find the dating channel that’s the best fit for you. In my experience, you should look for these two elements:

What channels have a large collection of my potential people?
What channels bring out my best self?

For example, I started my dating journey trying to meet women in city bars. It was a total disaster. Not only was I deeply uncomfortable in the high-energy pickup scene, but there were very few introverts like me out partying. My nights always ended with no phone numbers and no self-confidence.

When I finally tried online dating, with its focus on quality matchmaking and honest conversation, I knew instantly it was the perfect fit. Unlike the bar scene, I could line up promising dates with ease.

If you’re an extroverted party person, bars might be your perfect channel. If religion is your top priority, maybe you should focus on your place of worship. Just make sure you’re putting your time and energy into a channel that will work for you.

6. Always say yes to a good date.

If finding love is a top priority for you, then dating should be a top priority. Yes, dating can be tiring, expensive, and frustrating. But you have to keep showing up.

My rule was simple: If I had a promising date, I would be there in body, mind, and spirit. It didn’t matter if I was tired, busy, or over my monthly budget — I always showed up when it mattered.

Without this rule, my wife and I wouldn’t have met. She had been considering taking a break from dating and almost canceled our first date because she was tired. When I asked her out on a second date, she said yes on the spot, even though she already had dinner plans with her friend (who supportively rescheduled).

You never know if the next date could be the one. So if you spot a promising date, find a way to make it happen.

7. Each online dating service attracts a different type of person.

After trying over a dozen different online dating websites and apps, I realized they each tend to draw in a certain type of member. For example, eHarmony attracted an older, commitment-minded crowd. Coffee Meets Bagel attracted well-educated members. And Tinder attracted a care-free hookup crowd.

You’ll find each service has a distinct culture and community, which means some are a better fit than others for you. For example, I rarely got a date on Bumble, but my exact same profile on Coffee Meets Bagel easily attracted many dates.

Make sure you find the right pond to fish in. It’ll make a big difference.

8. Try multiple online dating services.

There are many dating services to choose from, so don’t pick just one and miss out on all the interesting people using others.

I’d recommend joining 1–3 mainstream services with large membership bases (access to the largest population of potential dates), plus 1–2 niche services that draw in the specific type of person you’re looking for.

I was on eight different apps when I met my wife, who was on two of my eight apps. You don’t have to be on eight apps if that feels overwhelming (trust me, it does). But if you’re on just one you’re probably missing out on some great people.

9. You have to fly your flag.

On dating profiles, people tend to play it safe. They say very little, appeal to common interests, and keep things general. My single friends used to joke that all profiles said the same thing: “I like fun, laughing, and pizza.”

A generic profile is one notch better than a blank profile. Everyone likes fun. Everyone likes laughing. Most people like pizza. After reading that, I have zero idea of what the person is like. On your profile, you need to do the opposite. Don’t try to fit in. Try to stand out.

When I started online dating, I tried to fit in and appeal to a broad audience. I said things like, “I love good food” and “I enjoy a fun weekend getaway.” I found I was attracting the wrong type of women and striking out with the women who seemed like a great match.

Finally, I got so frustrated I thought: I don’t care who I turn off. I’m just going to be who I am. I’m going to fly my flag. So I rewrote my entire profile to highlight things about me that were unique and specific. I said things like, “I enjoy a Saturday night curled up on the couch with a good thriller novel” and “I’m not much of a drinker, but I love a good cup of tea.”

Such statements were intentionally divisive. They turned away the party people and gave the introverts butterflies. Plus, they showed that I was self-aware and confident in who I was and what I wanted. Once I started to fly my flag, I found it easier to get dates and the people I met were much more like me.

You have to proudly fly your flag. Paint an interesting, authentic, and detailed picture of who you are that will act as a beacon for the type of person you want to attract. Don’t be afraid to say who you are, what you want, and what you don’t want. If you have deal-breakers or distinct interests, find a positive way to share them. But be nice, you don’t want to come across as difficult or rude.

Be clear about who you are and what you’re looking for. Not only will this authenticity turn away poor matches, but it’ll resonate with the people you want to attract. And this philosophy should carry over from your profile into your dates.

Dating is not the place to please everyone. It’s the place to find the right person for you. So write for your future partner, not for the masses.

10. Build a dating funnel and keep it full.

Anyone who’s worked in sales, marketing, or recruiting knows you have to build a prospect funnel: Draw in lots of unqualified candidates at the top of your funnel, and apply a series of screening steps to whittle them down to just a few highly qualified candidates at the bottom.

It’s the same concept with online dating. Your goal is to whittle a large pool of unqualified profiles down to a few highly qualified first dates.

For example, your dating funnel might look like this:

Total number of active profiles
% that meet your filter criteria
% that you read and find interesting
% that you contact
% that find you interesting
% that contact you back
% that agree to a first date
% you actually meet for a first date

Here’s the thing to remember: The more strict your screening criteria at each level, the more people you need to put into the top of the funnel to have high-quality dates come out the bottom.

For example, to find ten interesting people to message, I would often go through 100 profiles. And only about 10% of women I reached out to actually wrote me back. So after sending ten messages, I’d probably get one response. That one response led to a first date maybe half the time.

My goal was to consistently have 1–2 quality dates drop from my dating funnel each week. That required me to browse 200 profiles, send 20 messages, and chat with two women just to get one good date.

Your numbers could be higher or lower. It depends on many different factors. The point is if you want a steady stream of good dates, you have to do the hard work of browsing, contacting, and chatting with many prospects every week.

11. Don’t fall in love with a profile.

Early in my dating journey, I’d sometimes get emotionally invested in someone before we even met. I’d flip excitedly through her pictures, exchange cute messages, and nurture a growing feeling that she could be the one.

This almost always ended in disappointment. Real-life people tend to be different from their dating profiles. Sometimes it’s in a good way (e.g., they’re more passionate than you expected) and sometimes it’s in a bad way (e.g., their pictures are ten years old). Try to get to a first date quickly so you can find out if there’s something real there.

In my experience, it’s better to line up quality dates without investing too much emotion, and then show up in person with an open mind and open heart.

12. Online dating can be overwhelming.

From the moment you start online dating, you get a steady stream of messages, notifications, matches, promotions, alerts, tips, and more. It can be overwhelming. And the more dating services you use, the more noise you have to deal with.

Don’t let it discourage you. The key is to apply good matching criteria to filter out all the people you’re definitely not interested in so you can focus on the most promising candidates. This will greatly reduce the incoming volume while simultaneously increasing its quality.

Don’t feel like you need to respond to every alert. Just focus on the people who stand out.

13. When you get tired, don’t take a break.

I watched several friends go through their own dating journeys, and I noticed an interesting phenomenon: They’d date for a few months, get worn out and discouraged, and decide to “take a break from dating” and delete their dating profile.

I never agreed with that approach. I know dating can be a long, hard road. But don’t take yourself off the market. You could miss out on your moment of alignment.

Instead, raise your bar. Be a little pickier and go on fewer dates. That way you get a break, but you’re still on the market, and the few dates you go on will be high quality.

Whenever I wanted to take a break, I always revisited this quote from Ovid:

“Chance is always powerful. Let your hook be always cast; in the pool where you least expect it, there will be a fish.”

14. Learn to be a good conversationalist.

In my opinion, the key to a good first date is a good conversation. Sure, other things, like having fun, matter too. But the ultimate goal of the first date is to decide: Is there enough potential here to see this person again in a longer, more intimate setting?

Good conversation will help you confidently answer that question. Plus it will make a positive impression on your date. Not only will you learn about your potential partner, but they’ll love your thoughtful questions and witty banter.

The art of good conversation isn’t that hard to learn. There are a ton of educational resources available online. If you simply ask interesting questions, listen carefully to the answers, and ask thoughtful follow-ups, you’ll be 80% of the way towards being a great conversationalist.

15. Beware of people who don’t listen.

Every once in a while, I’d come across a non-stop talker. Someone who wasn’t interested in learning about me, but instead enjoyed being the center of the conversation for the entire date.

I’ll never forget I once sat through a two-hour dinner and my date never asked a single question about me. Not one.

If someone doesn’t ask you any questions, it’s a huge red flag that suggests five important things:

They lack some basic social and communication skills.
They’re not that interested in learning about you.
They have a self-centered worldview.
They’re not good at taking feedback, or they would’ve outgrown this bad habit by now.
They’ve surrounded themselves with friends or family who are also weak communicators.

To be fair, this could be my personal preference. You may enjoy listening or having the spotlight on someone else the entire time. But personally, I’d beware of anyone who shows up to a first date and doesn’t try to learn anything about their date.

16. Learn to read people using psychological profiles.

Even though everyone is unique, people often display a constellation of personality traits that fit neatly into known psychological profiles.

For example, I examined my closest friends and my best past relationships and found they were all different flavors of the INFJ personality type on the Myers-Briggs Type Indicator. After researching INFJ’s, I realized this extremely rare personality had distinctive traits and behaviors I could look for in potential dates. I also realized there were several personality types I clashed with, and I learned to spot their traits and behaviors too.

There are many ways to analyze people. Myers-Briggs worked well for me, but you might find luck with the Enneagram personality model, astrological signs, or something else.

If you look closely, you’ll see people come in patterns. Use that to your advantage by figuring out which patterns work for you and which don’t.

17. If you listen carefully, people will tell you who they are.

Over 100+ dates, I learned how to listen. I mean really listen. I learned that if you watch closely, people will show you who they really are.

Here’s an extreme, but memorable, example that has always stuck in my mind:

I was grabbing drinks with a fun, high-energy woman who worked in the nursing field (let’s call her Jane). After a half-hour, the conversation turned to a classic first date topic: pets. She told me she loves dogs and HATES cats. It went something like this:

“I don’t understand how anyone could ever like a cat,” Jane said.

I laughed, shifted uncomfortably on my barstool, and said, “Well, I’m a huge animal lover, so I enjoy both dogs and cats. I think maybe the reason ‘cat people’ like cats is because they’re a quirky blend of affectionate and mischievous. But I totally understand why they’re not for everyone.”

Jane stared at me for a moment, her mouth twisted in an expression of disgust, and said, “Yeah I don’t get how anyone could ever like a cat. They’re awful.”

Baked into that little exchange was a huge red flag about our communication styles. In under 30 seconds, Jane told me seven important things:

She’s outspoken about her opinions.
She has inflexible opinions on relatively minor issues.
She doesn’t consider opposing perspectives well.
She never considered that I could be a cat lover before saying she hates cats.
She doesn’t seem open to considering new information, preferring to simply restate her own original opinion.
She doesn’t have the emotional intelligence to at least acknowledge my theory on why some people like cats.
She’s not particularly concerned with making a negative impression on me just 30 minutes into our first date.

Now, I’m not trying to rip on Jane. She was a great person. But those insights strongly suggested we had an incompatible communication style, which was a dealbreaker for me. And she probably felt the same way about me. I’m sure she’s a great fit for someone, just not for me.

Usually, it’s not that obvious. But watch how people act to learn how they think. It’s like being a detective: What can you see on a first, second, or third date that will tell you if this person would be a good life partner for you?

18. Dating coaches can help you improve.

Your goal shouldn’t be to become the world’s best dater. It should be to find the right person for you ASAP. That said, if your rough dating skills are getting in the way of finding the right person, it’s worth doing some work to improve.

Dating coaches can help write your profile, take pictures, set up dates, improve your conversation skills, and more. And if you’re constantly striking out and you can’t figure out why, they can help you find your blind spots.

Halfway through my dating journey, I hired a dating coach to help improve my profile. It was expensive, but it made a huge difference. After that, I regularly got compliments on how genuine and funny my profile was.

Be honest: Are there major weak spots in your dating game that are holding you back from meeting the one? If so, you might consider asking a dating coach for help.

19. Trust your gut.

It’s important to listen to your gut when making big dating decisions. When I look back at some of my rocky relationships that lasted a few months, but ultimately didn’t work out, I can attribute the failure to red flags I spotted early on but chose to ignore. I wish I had trusted my gut.

Similarly, there were certain partners who seemed great on paper but when it came time to take our relationship to the next level, something in my gut screamed, “No!”. I’m sure there was a good reason.

Your gut shouldn’t be your sole decision-maker. But it should have a very important voice at the table.

20. Don’t trust your gut.

Watch out: Sometimes untrustworthy voices pretend to be your gut.

For example, I’ve heard friends declare, “My gut says I shouldn’t date him because he’s not tall enough.” Or, “My gut says I need a woman who’s extremely well-educated.”

Those things might be gut-verified deal-breakers, which is totally fine. But sometimes our ego will masquerade as our gut, acting as a voice of vanity rather than a voice of wisdom.

Always listen to your gut. But interrogate it a bit to make sure it’s not your ego in disguise.

21. Don’t get distracted by shiny objects.

When it comes to dating, we all have a weak spot, a guilty pleasure, a shiny object that can lure us in. Maybe you’re a sucker for an attractive body, a lot of money, or an impressive academic pedigree.

Be careful. Such siren songs rarely have lasting power. Once the excitement of your shiny object wears off, you’re left with the real person underneath. Trust in your list to keep you focused on what truly matters.

22. Don’t put too much focus on physical attraction.

There’s no denying it — a huge part of dating is physical attraction. We rely on profile pictures and side glances as our first decision criteria on whether someone is worth talking to.

You can’t ignore physical attraction. It’s a core part of love’s formula. But be careful not to weight it too heavily. Our bodies tend to fade over time, so you can bet those smoking-hot biceps won’t look the same in 20 years. At the same time, attraction tends to grow over time when you find the right person and experience life together.

There needs to be a baseline level of physical attraction before you move forward with someone. That said, putting all your eggs in the “hot bod” basket is probably a bad bet.

23. Love at first sight is a lie.

From a young age, Hollywood teaches us the first time we see our soulmate they’ll be surrounded by an angelic light, laughing in slow motion, and tossing back their windswept hair.

This is a bad soulmate test. At best, such take-your-breath-away moments are signs of physical attraction, not soul connection. Sorry, but the way she sparkles across the room has nothing to do with how compatible you guys are.

To be fair, love at first sight may work out for some people. But I’d guess that’s mostly luck. Focus on connecting where it matters, not on their radiant light.

24. Focus on how you feel.

It can be hard to know if your date is a good fit after just a few hours together. Is there long-term potential here? Should I go on a second date?

One of the best tests I’ve found is actually pretty simple: How does it feel when you’re together?

It should feel natural, easy, fun, relaxed, and strangely familiar. It should feel sort of like being around friends and family. It should feel like you already know them. It should leave you wanting more. That’s a sign your authentic selves are compatible.

I actually made a list of how I feel when I’m with my best friends and family, and I looked for shades of that same feeling when on my dates.

There’s a misconception that love should be hard work. I disagree. If it’s hard work on your first few dates, something is wrong. Instead, look for an easy, genuine, and familiar connection.

25. If you can’t say yes, the answer is no.

After a few good dates with someone, a natural question starts to arise: Should I stop meeting new people and date this person exclusively?

It’s a tough question, and the answer likely falls under that squishy category, “When you know, you know.”

When I was facing such a situation, I used a simple rule: If you can’t say yes, the answer is no.

In other words, if you’re not excited enough about this person to confidently say, “Yes, I want us to be exclusive,” then you’re probably not ready to escalate the relationship.

26. If it’s not right, you have to move on.

Dating is a test drive for a long-term relationship. Both parties go in with an open mind and open heart, genuinely hoping things will work out. Usually, they don’t, and that’s OK.

Once you know the relationship isn’t going to last, you have to move on. It’s not fair to waste your time or your partner’s time if the match has no future. Don’t drag them along, be vague about how you feel, or hang around to enjoy a warm bed.

Breakups are hard, but once you see the writing on the wall, you have to be honest. The sooner you both move on, the sooner you’ll find that special someone searching for you.

27. Rejection is a painful gift.

Dating can be rough. You’re going to reject some dates, and some dates are going to reject you.

Rejection comes in many forms. Most dates will just stop communicating once they lose interest (known as “ghosting”), while others may tell you directly they’re not feeling it. Some may even stand you up and skip out on a planned date (this only happened to me once, thankfully).

Regardless of what form it takes, rejection hurts. But if you can look past the pain, you’ll see it’s actually a gift. It saves you a ton of time, money, and energy. Your date is telling you loud and clear: “We’re not a fit.” And if they feel that way after just a few dates, a full-blown relationship almost certainly won’t work out.

Also, it’s critical to look for themes in your rejections. Do you keep striking out with similar people? Is there something you’re doing that’s turning them off? Look past the pain and try to improve for your next date.

Don’t take it personally. It’s part of the game. Even though it doesn’t feel good, your date is giving you a clear-cut answer which allows you to put your precious time and energy into something better.

28. Prepare yourself: It could be a long, hard road.

Finding true love is a process that can’t be rushed without compromising quality. Meeting the right person requires almost-magical serendipity, or what I call “The Alignment.”

My dating journey, which lasted well into my 30’s, took way longer than I ever expected. There were many frustrating stretches where I felt like I couldn’t keep looking, not knowing I still had many years and dates ahead before I’d finally meet my wife. At moments, dating felt like a part-time job, a depressing grind, and a cross to bear. It’s hard to feel alone.

Early in my dating journey, every little bump and bruise hurt. Over time, my skin thickened. That made the ups and downs easier, but it also made me cynical and hardened my heart. Searching unsuccessfully for love for years on end takes something from you. It steals some of the magic of falling in love and turns it into hard work.

I hope you find your soulmate tomorrow. But if it takes a while, don’t let it get you down and don’t settle. Have patience and have faith that your special someone is worth a hard journey. It’s more important to get it right than to get it right now.

29. Learn and grow through experience.

If you’re new to dating and relationships, you’re probably going to need some on-the-job learning.

It’ll take a few dates and relationships before you figure out what works for you and what doesn’t. You’ll learn about people, partners, what makes you tick, and what makes others tick. The more experience you gather, the wiser you’ll be, and the closer you’ll come to finding your special someone.

I look back at some early dating partners I walked away from and see they were actually a good fit for me. And I look back at other relationships I fought hard to keep alive and see the fit was totally wrong from the start. Put simply, I made many, many mistakes along the way.

Love, much like life, is a winding road. You have to live it to learn it. Try not to look at the inevitable twisting and turning as a failure or wasted time. It’s wisdom and life experience. It’s your one-and-only journey to find love.

30. Nobody’s perfect. But are they perfect for you?

I dated for a long time. Along the way, people would often say, “You know, nobody’s perfect!”

I hated that. It felt like their condescending way of saying, “Stop being picky and settle like the rest of us!”

After a long dating journey with a very happy ending, I’d like to offer my own version: “Nobody’s perfect. But you can find someone perfect for you.”

I’ve observed that every partnership has its friction points. Looking for a relationship with zero friction is a bad strategy. There will always be little things that don’t quite align.

That said, if you look hard enough, I think you absolutely can find someone who is a perfect fit for you. That means you align where it matters most.

Focus on the important stuff, and let the little stuff fade away.

I’ll leave you with one of my favorite quotes from Steve Jobs’ famous Stanford speech. These words kept me going through many dark nights:

If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it. And, like any great relationship, it just gets better and better as the years roll on. So keep looking until you find it. Don’t settle.

One small request: Please forward this to someone who would enjoy it. There’s an open seat by the fire :)

Fireside Philosophy by Todd Lincoln

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