Let me tell you about my client Daniel (changed his real name because he’d like to stay anonymous).
Daniel is kind, emotionally aware, genuinely funny, the kind of person who remembers your favorite coffee order and texts you when a song reminds him of your story. By every measure, he’s what people say they want in a partner.
But last spring, in one of our weekly sessions said something that broke my heart a little: “I think I’m just bad at this.”
He’d been on 19 first dates in four months. Nineteen. Some through apps, some through mutual friends, some through that hopeful magic of “just putting yourself out there.” And not one had led to a second date.
I asked him what happened on the dates. He pulled up his notes app, yes, he kept notes aaand read me a list of conversation topics he’d prepared. Bullet points. Structured like a job interview.
“He wasn’t bad at dating. He was performing connection instead of experiencing it.”
Here’s what I’ve come to believe after years of coaching people when it comes to love and relationships: modern dating has quietly taught us that we need to “win” a first date. That we need to arrive polished, impressive, and strategically likable.
But here’s the thing, real connection doesn’t happen in a performance!! It happens in the gaps, in the awkward pause when you both laugh at the same time, in the moment you say something honest instead of clever, in the vulnerability of being a little imperfect in front of someone new.
3 Shifts that Change Everything
Stop trying to be impressive. Try being present instead. Before your next date, put your phone on Do Not Disturb before you even walk in. Take three slow breaths in the parking lot. Decide that your only job tonight is to be genuinely curious about this other human.
Ask questions that have no right answer. Instead of “What do you do for work?”, try “What’s something you’ve been really into lately that surprises even you?” Watch how the energy in the room changes.
Let them see something real about you. Not your trauma, not your rehearsed story of how you got here, just one small honest thing. “I was genuinely nervous coming here tonight.” That kind of truth is soooo refreshing!
What happened to Daniel you ask?
He went on one more date. Except this time, he left the notes app at home. He told the person across from him that he’d been treating dating like a test he needed to pass and that he was trying something different tonight.
She laughed. Then she said, “Me too. Can we just... talk?”
They’re still talking. Six months in.
So I’m here to tell you that you are not bad at this! You’ve just been playing by rules that were never designed to help you find love.
I can help you with that.
