flirt with the world

the work isn’t to stop wanting love. it’s to love yourself so much that you no longer fear its absence

I recently took a detour from a work trip to visit a girl I had a crush on in high school. We met through mutual friends, were never in the same city, and never quite single at the same time. After catching up over the phone a few weeks ago, I figured—why not visit? The last time I saw her in person was three years ago. Worst case, I’d leave with a story. Best case? Maybe I’d meet my future wife (LOL).

We spent an entire day together, and it quickly became clear the connection was more platonic. My flirts weren’t really reciprocated. The next day, I asked if she’d prefer I interacted with her with no romantic intent—she said yes, and just wanted to stay friends. It was disappointing, but also clarifying. And honestly, I walked away with a lot to feel and reflect on.

Because it’s rare for me to really like someone, I sometimes get emotionally ahead of myself. That can show up as overeagerness—an energy that might feel like pressure to the other person. Still, I’m glad I was honest about how I felt. Three-years-ago me wouldn’t have had that kind of boldness. Attraction is such a tricky art—it's always a dance between being open and not overwhelming, between expressing interest and staying grounded.

Underneath that eagerness is the inner kid in me who craves intimacy and connection. That craving isn’t bad—it’s human. The issue is when it takes over and I lose my groundedness—when I shift from presence into seeking, from wholeness into lack. I forgot that everything I seek is within.

On the flight back to New York, I spent an hour talking to my ChatGPT therapist (it actually knows me better than my real therapist), trying to make sense of everything. That conversation helped me realize something that felt obvious in hindsight: the qualities I was drawn to in her are the same ones I want to cultivate in myself. Sometimes, our crushes are just misplaced ambitions.

These feelings reflect the parts of me I want to develop.
The traits I admire are often a mirror—showing me what I value and want to embody more of.

She’s introspective and extraverted. Goofy and kind. She talks to strangers in stores. Her eyes light up when she finds a cool vintage jacket. She’s active, values her mental and physical health. Growth-minded. Grounded. She embraces the cultures that shaped her. She’s independent—drives, navigates, cooks, kills bugs—but still soft and open-hearted.

Getting to know her clarified what my “type” is. There were so many little moments that made me feel giddy. She had so many qualities I value and find attractive. I jokingly call her my dream girl when I catch up with friends.

But I also know that kind of infatuation often comes from projection—not reality. It’s a mirror, not a map—reflecting what I aspire to, or what I want to see in myself.

Because meeting someone like her felt so rare, I got infatuated quickly. My mind jumped into “she’s the one, I need to date her” mode—like it was a checkbox to check. But that’s the trap: treating connection like a task instead of a dance. A good relationship isn’t something you force into place—it’s something you grow into, together. It happens when you stay present, enjoy each other’s company, and let things unfold. “Finding someone” shouldn’t be the goal. It should be the byproduct of you enjoying your life.

That brought me back to something that’s been on my mind: I want to shift into simply enjoying being myself and being with myself. Having fun with my life—for me. Not as a strategy to meet someone, but because I genuinely enjoy my own company. Just living. ChatGPT gave me a quote that really stuck:

“The work isn’t to stop wanting love. It’s to love yourself so much that you no longer fear its absence.”

That’s the north star. Build a life where love is an overflow—not a finish line.

Looking back, I can see the progress I’ve made with all this inner work. I stayed in my body. Embraced any emotions. Said what felt true. Didn’t beat myself up. Did what I could for things within my control.

And honestly? I feel joyful. Yeah, a little disappointed—but also proud. The experience brought clarity. And energy.

I’m back in NYC now, feeling excited. I deleted the dating apps. They made “finding someone” feel like a job to be done and a problem to be solved. Instead, I’m just doing random stuff that feels like fun. I signed up for a ClassPass trial. Went to a café and talked to someone sitting next to me—turns out we live in the same building. Complimented a barista on his tattoo and he shared how the artist messed it up the first time. Dragged my roommate to sign up for a comedy night in a sauna. Playing a lot of volleyball and badminton.

Summer’s coming. The weather’s been incredible. Life feels good.

I’m just gonna do things for the joy of it. It’s my flirt with the world era.