November 17

What I Wish I’d Known When I Started Dating

Photographer: Mindy Sabiston | Source: UnsplashPhotographer: Mindy Sabiston | Source: Unsplash

Our relationships are the greatest predictor of our long-term happiness. Romantic relationships bring us unparalleled joy when they work and a lot of grief when they don’t. There are so many things I wish I'd known when I started dating that would have saved me a lot of heartaches, time, and money.

You may not be able to change the past, but you can learn from what happened and make better decisions in the future.

Navigating romantic relationships is a vital skill for adult life. It's something we should have learned in school but never did. At the age of 44, it's still something I'm learning how to do.

Cultural Conditioning

Hassan Minaj joked that for the first 25 years of your life, Indian parents tell you "don't talk to girls." But right after you turn 25, the narrative changes to "why don't you have a girlfriend?"

  • Some people learn about courtship from their parents,
  • But mine had an arranged marriage, so there was nothing they could teach me either.

After years of going on first dates that never led to second dates, I did the only thing I could think of: I joined a cult.

The Seduction Community

started dating

The cult that I eagerly joined in my early 20's eventually gained notoriety as the seduction community. This movement ultimately culminated in the publication of Neil Strauss's wildly popular book, The Game.

  • The potential to meet women determined every choice I made about what to do, where to go, and how to spend my time.
  • I missed out on opportunities to travel with friends, grow as a person, and explore things that made me curious.

It took me a long time to realize that it's more attractive to live an Insanely Interesting life than is to pretend you do.

The Relationships

Jerry Colonna asks people to reflect deeply on the question, "How have I been complicit in creating or perpetuating the conditions I've created?" Whether it's a delight or a disaster, two people determine a relationship. And I was just as complicit in my relationships that didn't work as the people who I dated.

The one thing my two longest relationships had in common was that I knew, almost instinctively, that I would end them just three weeks after they started. Both of the girls I was with weren't right for me, and vice versa. But out of a paralyzing fear of being alone, I stayed in those relationships, clinging to them for far longer than I should have.

Now, looking back, I realize how incredibly selfish that was of me. With that in mind, here are the most important things I wish I'd known when I started dating.

7 Things I wish I Knew When I Started Dating

started dating
Photographer: Priscilla Du Preez | Source: Unsplash

We all have want author Logan Ury calls Dating Blind Spots

Dating blind spots are patterns of behavior that hold them back from finding love, but which they can't identify on their own. Your tendency impacts your behavior at every stage of the relationship, so it's crucial to learn yours as the first step along your journey to finding love- Logan Ury, How Not to Die Alone

Until you become aware of your blind spots, you're likely to repeat the same patterns.

1. Real Love isn't a Romantic Comedy; it's often messy, complicated, and unpredictable.

started dating

For a good amount of my life, I was what you might call a hopeless romantic. I thought people fell in love the same way they do in the movies.

When I was in a long-distance relationship, I was already imagining the screenplay for a movie called "Love in 20 Cities." I was so excited to document our journey together, to capture the ups and downs of our love as we traveled from city to city. But she broke up with me after the third city. And just like that, the story I had been so excited to tell came to an abrupt end.

  • If you are courting someone and stand outside their window blasting a Peter Gabriel song on a boombox, they won't fall in love with you. You'll probably get arrested for disturbing the peace because you're not John Cusack.
  • If you confess your undying love to a woman who doesn't even know you exist, it's probably not going to end with Jennifer Love Hewitt kissing you at a train station.

In case it isn't clear, I've watched way too many romantic comedies.

In romantic comedies, love unfolds in a way that we mistake for "happily ever after." But real life is not a Disney movie. False beliefs about romance based on popular culture are a recipe for poor relationship decisions and unrealistic expectations.

One common message in childhood fairy tales and in adolescent romantic tragedies is the notion that fate is responsible for people falling in love. However, these messages of fated love, suggesting that love "just happens" or that people magically "live happily ever after," are not only quixotic but also counterproductive. One of the problems in modern romance is that trusting in fate leads people to look for love in the wrong places and instills false beliefs about how love endures, Ty Tashiro, The Science of Happily Ever After

Hopeless romantics don't have much hope for starting a successful relationship until they realize that love is more complex than what they see on screen. I'm still a romantic at heart, but after 44 years, I've learned to stay grounded in reality.

The Importance of Having Healthy Boundaries

Looking back, I can now see that one glaring issue all my failed relationships had in common: a complete and utter lack of boundaries.

The Cost of Having Bad Boundaries

The cost of bad boundaries is immense. It leads to conflict-ridden, imbalanced relationships, a lack of agency over our own time, and general malaise. -Terri Cole, Boundary Boss

Because I didn't have any boundaries in my life, I often found myself spending money I couldn't afford to spend, allowing the people I dated to emotionally abuse me, and refusing to speak up about anything that was bothering me.

When you have loose boundaries and never speak up, resentment gradually builds. This is why it's important to communicate one's boundaries in a relationship and let people know what is and isn't ok for us.

Healthy Boundaries

When we have healthy boundaries, we avoid emotional harm, and it's less likely that people will hurt or take advantage of us. We have to be willing to say what's acceptable to us and what's not.

And the risk of expressing our boundaries is that we may lose the person we're with. But if we don't express our boundaries in the short run, we'll eventually resent them in the long run, and the relationship will end regardless. So how do we develop healthy boundaries?

3. True Confidence

In his book Models, Mark Manson says that "true confidence is being more interested in your perception of yourself than someone else's perception of you."

But the funny thing is we go through life doing the exact opposite by trying to impress people we want to date and gain their approval, which paradoxically has the opposite effect.

Does that mean everyone will like you because you have true confidence? Of course not. You're still going to get dumped, have your heart broken, and deal with all the parts of relationships that suck.

Individual opinions aren't universal truths. Just because you're not a fit for one person, it doesn't mean you're unlovable or that something is wrong with you. If I hadn't come to this realization, I would have actually believed it when an Indian mother referred to me as "Srini the loser" on a dating show.

Lukewarm Romance is Worse Than None

When I started dating, I spent a lot of my life chasing women who were not interested in me. And in a lot of cases, when I became evasive, they became interested. But if this is the game you have to play, then you'll inevitably lose. Not only that, it's emotionally exhausting and inauthentic.

When someone's feelings about you are lukewarm, hoping their feelings will change is a fool's errand. The time you waste with someone whose feelings for you are lukewarm is time you could have spent connecting with someone who is truly excited about you.

As Mark Manson says in one of his most popular articles, "Why would you ever choose to be with someone who is not excited to be with you?"

4. Nobody Completes You

The person you're in a relationship with doesn't complete your life; they should complement it. In our interview on the Unmistakable Creative, author Jennifer Taitz said, "Your person can't be your everything. That's not going to realistically fulfill you. It seems like a really poor investment to, let's just say metaphorically, take all your diverse portfolio and put it into one risky stock."

5. Don't Avoid Fights

According to Eric Barker's book Plays Well with Others "Fighting doesn't end marriages; avoiding conflict does. A study of newlyweds showed that, early on, couples who rarely fought couples turned out to be on their way to divorce when researchers checked back in after three years.

When I started dating, I avoided fights because I didn't have healthy boundaries. To me, a fight always meant that someone would break up with me if I fought back. Of course, a relationship where all you do is fight sucks. But one where you do///n't fight at all is probably too good to be true.

6. Don't Put So Much Pressure on Yourself

The point of the first date isn't to decide if you want to marry someone or not. It's to see if you're curious about the person, if there's something about them that makes you feel like you would enjoy spending more time together- Logan Ury, How not to Die Alone

Between the cultural conditioning, I had experienced and the immense pressure I was putting on myself, I went into every single date with high hopes of meeting my future wife. Eventually, I came to the realization that this was an incredible amount of pressure to put on someone I had never even met before.

Rather than dwell on relationships that didn't work out or first dates that fizzled, I've chosen to focus on the positive attributes in every person I've met. By doing so, I've been able to identify qualities I'd like in a future partner, and this has helped me to be content and happy while single.

As the musician AR Rahman once said, when you expect nothing, everything comes to you.

7. Let go of How You Thought It Would Be

At age 44, I've come to terms with the possibility that I'll never have biological children even though I want them.

But I'd rather be with someone I love who can't have kids than someone I don't love that can. If two people who don't love each other bring a kid into the world, it's a disservice to that child.

Terri Cole once said to me, "You have to let go of the way you thought it would be to open yourself up to all the amazing ways it could be."

There's a difference between having standards and having expectations. Standards are great, but expectations can be limiting in love and every area of life.

Three Pillars to a Relationship

After reflecting on previous relationships that didn't work, I developed this framework for finding a long-term partner. This is an oversimplified version of three pillars; within each, there are dozens of sub-pillars.


Call it attraction or call it chemistry, but either way, it's an essential component of any successful relationship. Without this spark, no matter how much you're in love with someone, the relationship between you and that person will usually remain platonic. While it's true that friends can fall in love, the romantic comedies that depict this happening are often far from realistic. In real life, things rarely end up as neatly as they do in the movies.


Chemistry without connection is lust. But chemistry combined with a connection could be the first sign that you're falling in love.

  • When you form a true connection with someone, they accept you as you are.
  • They give you permission to be yourself, warts and all.

When you connect with someone, what you feel for each other transcends the physical and becomes emotional.

I've always thought I hated talking to the girls I'm dating on the phone. But then I met someone who completely changed my perspective. We were able to talk for hours on end, sometimes up to three hours a day. It wasn't until my sister pointed it out that I realized I didn't actually hate talking on the phone. Rather, I just hadn't found someone I truly connected with before.


You could have an amazing connection and chemistry with someone. But you might be incompatible for several reasons.


If someone has just gotten out of a relationship, they may be healing from heartbreak. When someone hasn't recovered from a previous relationship and tries to start a new one, it usually ends up being a rebound.

That's fine if you just want to get laid, but probably not so much if you want a long-term relationship. In their effort to heal from heartbreak, they might unintentionally break yours.


Sometimes distance can lead to incompatibility, despite having incredible chemistry and a deep connection with someone. If you live in one country and someone else is on the other side of the world, that would make it challenging for the relationship to work.


Values play a much bigger role in compatibility than almost any other factor. Partner Choice is a Strong Predictor of Relationship Success.

Although supportive friends, self-confidence, and communication skills contribute to healthy romantic relationships, a much stronger predictor of romantic success is the type of partner you choose in the first place. The traits that a partner possesses before you ever start dating—such as his or her personality and values—are among the strongest indicators of whether a romantic relationship will be happy and stable many years later. -Ty Tashiro, The Science of Happily Ever After

If we choose people whose values are not aligned with ours, the likelihood of a successful relationship will decline. None of these categories are mutually exclusive, and there are hundreds of subcategories within them. So this is a simplistic way to think about these things.

The Most Important Thing I Wish I Knew When I Started Dating

Like every other aspect of life, you can't change the past. But you can Learn from the outcomes of every decision you make. And if there's one thing I really, truly wish I'd known when I first started dating, it's that bad dates, relationships that don't work out, and heartbreak are all an inevitable, necessary price of admission for finding lasting, meaningful love.

The Relationship and Dating Interview Collection

Get access to our collection of interviews from the Unmistakable Creative that will help you understand what makes relationships last, discover your values, and live an extraordinary life regardless of your circumstances. Our interviews will provide you with the insights and strategies you need to take your relationships to the next level, and to create a life that is truly fulfilling. Click Here


You may also like