The Art of Going on a Date You Already Know Won’t Work
Sometimes you’re not meeting your husband. You’re collecting a Tuesday night anecdote.
If I’m a painter, this subject is my Mona Lisa.
I know this canvas. I know the brush strokes. I know the lighting, I know how to flirt my way around it without promising more than I mean to.
Because here’s the truth no one wants to say out loud: sometimes you say yes to a date already knowing it’s not your forever.
And that doesn’t make you cruel, or that you wasting someones time.
It makes you curious.
Lately, I’ve had at least four separate conversations with people who are putting Olympic-level pressure on a single date. Like it’s an audition for marriage... Like if it doesn’t spark fireworks, a string quartet, and a five-year plan by dessert, then something is wrong.
Can we exhale?!
A date is not a contract.
It’s a conversation with appetizers.
We’ve turned modern dating into this hyper-analyzed performance review.
Did he text fast enough?
Did she laugh too much?
Was there chemistry?
Was there potential?
Can you see yourself raising golden retrievers together?
It was ice cream!!
Sometimes I go on a date knowing it probably won’t work because our values don’t line up long term. Or our ambition levels are mismatched. Or I can already tell the life trajectories are pointing in different directions.
But that doesn’t mean I can’t enjoy a Tuesday night story.
There’s something beautifully low-stakes about sitting across from someone and simply being present. With no Pinterest wedding board in your head. Just two people practicing conversation and bater.
The art is in knowing the difference between:
Leading someone on
And letting someone take you to dinner
One is manipulation.
The other is maturity.
I think we underestimate how healthy it is to gather data. To observe how you feel. To confirm your standards in real time. To walk away thinking, “He’s a good guy. Just not my guy.”
That sentence is allowed.
We act like declining a second date is a moral failure.
It’s not.
And honestly? Sometimes going on a date you know won’t work is just honoring the fact that someone was brave enough to shoot their shot. It doesn’t cost you your identity to sit at a table for 90 minutes.
The key is intention.
I’m not going to pretend I’m open to a future I’ve already decided isn’t aligned. I’m not going to romanticize potential I don’t believe in. I’m not going to let politeness blur my standards.
But I am allowed to say yes to a moment… uh yeah.
There’s also a quiet confidence in knowing you won’t get swept away. In knowing you can flirt, laugh, hold eye contact, and still walk away unaffected.
Not every date is destiny.
Not every connection needs to be stretched into something it isn’t.
Sometimes it’s just two people practicing being human.
And if I’m honest, I think more people would enjoy dating if they stopped treating every first date like a final exam.
Thank you for coming to my TED Talk.
Until Next Blog,
