Why Dating “Success” Didn’t Mean I Was Prepared for Love

If you asked 25-year-old me whether I’d ever hire a dating coach, I would’ve laughed.

That was for clingy, obsessive women.

Not ambitious, self-sufficient, future-CEO types like me.

Back then, I took a laissez-faire approach to love. Breakups were sad but normal. Cheating happened. There were always more fish in the sea. I didn’t feel anxious, didn’t need reassurance, and honestly found that kind of behavior cringey in my friends.

Men sent flowers. They planned dates. They took me to operas and trips just to try to be my boyfriend.

I truly believed I was equipped for relationships!  I just hadn’t met the right guy yet.

The Dating Shift in My 30s

At 31, I outgrew a four-year relationship with a genuinely kind man.

We tried to decouple gracefully. We experimented. We attempted an open relationship. Eventually, I had to admit: I didn’t know how to make it work.

What I didn’t realize at the time was that dating at 32 is not dating at 25.

At 25, dating meant bar-hopping, house parties, and constant social exposure. There were endless opportunities to meet someone new or distract yourself from someone old.

But at 32? I had never been on a dating app; men were now coming off divorces or had baby moms in the mix. Bars were for catching up with the girls, not meeting guys.

It felt like waking up in a completely different world. And this new world came with a level of emotional turmoil I was gravely unprepared for. I was finally dating as an adult, with a career and real hopes of cohabiting, traveling, and growing old together with someone. A lot more was at stake than before. That la ze faire girl was GONE!

Short, intense connections activated parts of my heart I didn’t know existed and dragged unresolved relational patterns straight to the surface. 

Here’s What I Learned the Hard Way

1. Most of us are emotionally untrained for modern dating.

We are not taught how to handle rejection, flaking, ghosting, or deception. Every unwanted outcome triggers the same core wound: “I’m not enough.”

Emotional maturity isn’t avoiding pain.

It’s learning how to recover quickly and stay open anyway.

2. Dating requires discipline, not just self-awareness!

It’s like trying to lose those extra 20lbs or play Mozart level piano. In a culture obsessed with “honoring your feelings,” it’s tempting to quit the moment dating hurts. But discipline means showing up even when it’s uncomfortable.

If you say you’re dating twice a week, you date twice a week.

That’s how self-trust and confidence are built.

3. Therapy-speak will sabotage you

“He’s avoidant.”

“He lacks capacity.”

“He just needs healing.”

Diagnosing men to soothe your disappointment is not empowerment — it’s bullying. I spent years infantilizing grown men’s decisions while simultaneously lowering my standards and waiting around for their potential. It’s far more useful to develop the skill of disappointment recovery than to spiral into someone else’s imagined trauma. 

What Freedom in Dating Actually Looks Like

Love doesn’t happen when you indulge every emotion. It happens when you’re no longer ruled by them. Unchecked, emotional indulgence will push you into two dead ends:

1. Retreating into “healing” as a socially acceptable form of hiding

2. Attacking men as a defense against rejection

Neither leads to partnership (or A WEDDING RING)!!!!

The Woman I Became

It took time to dismantle my beliefs about men, dating apps, and relationships.

It took discipline to keep showing up when dating wasn’t fun or flattering. But that work mattered because marriages don’t avoid bad days. And I wouldn’t want any man tied to the entitled, blame-driven, emotionally fragile version of me.

I deserve a partnership because I built the skills required to sustain it. When you’re no longer easily shaken, men feel it. They relax. They engage. They invest. Not because you’re perfect but because you’re free.

Dating is like breathing to me now. I can tell I’m going to be asked for a second date 30 minutes into meeting someone. I am the obvious fucking choice, and I earned that title through rejection, tears, sleepless nights AND still showing up.

That’s not luck.

That’s repeating the strategy and the somatics!