What’s The Real Definition
Of Romantic Success?

I love hearing romantic success stories. Even after eleven years, I still get a huge smile on my face when a client shares their enthusiasm from a positive dating experience.

That’s why it’s so difficult when I sometimes have to challenge people on their so-called “successes”. It’s tough to tell them to temper their excitement because their victories may not really be victories.

A lot of people define their romantic success by the wrong metrics. I know this because I spent years measuring my love life wrong, too.

I used to think I was crushing it with women if I got a number, got a kiss, or got laid. It seemed pretty straightforward…

“If an attractive woman wants me, I must be doing something right.” Society and friends told me that dating success was only about sleeping with hot women.

But over time I realized that mindset was all backwards. Viewing dating in this way never brought me long-term fulfillment.

I was stuck chasing the next “win” and without it, I felt like a failure. I never became comfortable in my own skin. And I never found lasting relationships with the women I really wanted.

Because when you measure your dating success by external approval, you risk destroying your self-esteem.

Winning Is The Opposite Of What You Think

Self creation

Wikipedia defines self-esteem as…

“An individual’s overall subjective emotional evaluation of their own worth. It is the decision made by an individual as an attitude towards the self.”

Self-esteem is how you view and love yourself for your internal qualities. It’s not how other people see you nor is it how you measure up to arbitrary societal standards.

I know attractive people who think they’re ugly and overweight people who absolutely love themselves. I know rich people who are miserable and poor people who are grateful for every day they’re on this Earth.

It’s not easy to suddenly adopt a healthy attitude towards ourselves. But you can start by honestly evaluating your behavior with women. Because your behavior constantly influences how you feel about yourself.

Your subconscious is always listening and over time, your actions will either raise or lower your self-esteem.

So think…

Do you often act in self-love, self-compassion, and self-acceptance? Do your actions align with your deeper values? Do you respect yourself and set your boundaries when you feel disrespected?

Do you prioritize your needs or do you hide them in fear of facing disapproval or judgment of others? Do you try to speak honestly and express who you are even it means other people may not agree?

THESE are the questions that should dictate your successes – in dating and in life.

Just because you hooked up with a hot girl doesn’t matter if you had to compromise your values to do it. Your self-worth suffers all for what…a fleeting orgasm?

Some Wins Are Bad For You

The real loss

I know what you’re thinking…how can dating an attractive person ever be a bad thing?

Again, it all depends on whether or not you’re sacrificing your self-esteem in the process.

Let me give you an example…

Maybe you finally got that gorgeous woman from your class to grab drinks with you. You had a seemingly great date. She laughed throughout the conversation, looked like she was having fun, and you even kissed her on the walk home.

That’s amazing, right?

But what if that same girl blew you off for weeks before now and cancelled multiple times last-minute? What if she only talked about herself the whole time and you went along with it to please her?

What if you avoided expressing your more quirky interests because you thought she would judge you? What if she was on her phone, casually ignoring you throughout the date but you never expressed that you wanted her to be present?

So yes, you got this girl to go out with you…but what did you sacrifice in return?

Did you feel heard and accepted for who you are? Do you think she respects you as an individual? Is she attracted to you or just the version you pretended to be? And it is worth pursuing someone who connected with you under false pretenses?

Most importantly, prioritizing her approval tells your inner critic that the real you wasn’t good enough. You reinforce that you need to pretend to be somebody else to be a desirable person. And that’s guaranteed to crush your self-esteem.

That doesn’t sound like success to me.

Bad Wins Will Sabotage Your Future Success

Ticking time bomb

On top of lowering your self-esteem, measuring romantic success based on external “wins” sets you up for future failure.

You might believe that people will like you more if you figure out exactly what they want. But this only communicates to others that you’re desperate for their validation — and that’s a turnoff for almost everyone.

Being a chameleon is unsustainable. You’ll only find people who are attracted to that fake version of yourself. Simultaneously, you’ll push away people who would actually like you for you. And when you finally can’t keep up the charade, you’ll either lose your connections or end up being someone’s doormat.

The good thing is…there isn’t just one type of attractive person. Confidence is the sexiest quality imaginable – and it comes in all different forms and variations. And it’s something you can develop.

I have a client who recently started dating a girl who smokes. He told me that he knew he could never have a long-term relationship with a smoker.

He was afraid of being honest with her in case she didn’t want to see him again. He was thinking, “I can’t lose this connection” instead of “I need to stay true to myself.”

I told him to tell her the truth: that he was interested in casually dating, but that was it.

So what happened when he opened up to her on their second date? She went back to his place and they had sex.

He expressed what he wanted and even though it was different than what she wanted, she still found that self-confidence sexy as hell.

If you make your dating successes about self-love, you build real confidence and become more attractive to the people who genuinely appreciate you. That’s how strong, lasting relationships are formed.

If you make your successes about pleasing everybody, you may get a temporary high. But you’ll form connections with incompatible people, built on weak foundations, that will inevitably crumble.

Measure Your Internal Effort, Not Just The External Result

Love yourself

You need to evaluate your successes based on your effort to remain true to your values and respect yourself, not on the external result of women’s approval.

External approval: You introduced yourself to a woman with a rehearsed line you read from the internet.

Internal approval: You introduced yourself to a woman with something you genuinely felt or observed in the moment.

External approval: You let your cute co-worker rely on you and spend a lot of time together at work. You secretly liked her but only acted like her business buddy for months. You went above and beyond to help her on the job but never invited her to get more personal outside of work.

Internal approval: You invited your co-worker out, even if it meant you could find out she only saw you as a friend. You preferred to be upfront with your intentions rather than live in a fantasy world.

External approval: You finally got a girl to commit to a first date, but only after multiple last-minute cancellations and overall poor communication from her.

Internal approval: You walked away and focused on someone who was willing to invest in you. Or, you communicated your boundaries after she cancelled a second time: “My time is really valuable to me and I want to connect with someone who’s excited to connect with me.”

External approval: You had sex with a woman, but you had to pressure her or emotionally manipulate her into it.

Internal approval: You developed trust and comfort with a woman and had sex because of it. Or, she wasn’t quite ready yet, and you accepted her decision. Then, you waited until she was more comfortable or you chose to connect with someone else who reciprocated your desire.

External approval: You got a girl’s number, but you did so under the guise of being friends or helping her study.

Internal approval: You honestly invited a girl out to get to know her better on a personal level, even if that meant she might say no. The number was just a nice bonus.

External approval: You used your wealth and status to attract dates. You felt you needed to pay for expensive meals and experiences to get women to go out with you.

Internal approval: You used your personality to attract women because you want someone to like you for you. You bought some meals and split others. You invested money on dates only when you felt someone was authentically investing back in you.

External approval: You continued to date women who you knew wanted something more serious, even though you weren’t that interested in them. You wanted the attention even though you knew you were settling.

Internal approval: You broke it off with women you settled for to pursue women you genuinely desired. Or, you told those women you were only interested in a casual relationship with them.

External approval: You’re happy that a girl was so engaged and talkative on your first date. You purposely only talked about what she was interested in and avoided revealing your passions in case she didn’t find them appealing.

Internal approval: You shared your real perspective on things that matter to you and asked questions about subjects that engage you, too. You did this at the risk of her judging your hobbies, opinions, and interests.

Funny thing is, small internal wins end up leading to big external results.