The Lost Art of Shooting Your Shot
By Eryn | Meet Cute Club
UPDATE NOTE: Follow-up detail pending — friend and sister were planning to go back to the restaurant and sit at the bar. If something comes of it, this blog gets a Part 2.
A friend of mine was at dinner the other night with her husband, a friend and her single sister. The manager came by to check on the table. Everything was great, they said. The meal was wonderful.
Later, in the parking lot, the group was doing what groups do after good dinners — lingering, recapping, not quite ready to leave. The manager came out to let them know their table had been cleared and checked to make sure they were finished.
After they thanked him, the sister turned to him and said: “I’m single. Are you?”
He was flustered. He was. He told her yes.
My friend was astonished. “You don’t see people do that anymore,” she told me. “Just outright shoot their shot like that.”
She’s right. And I’ve been thinking about it ever since.
What we used to do
There’s an old social practice — mostly attributed to the Victorian era, though it existed in various forms long before — called dropping the handkerchief. A woman who was interested in a man would let her handkerchief fall near him. An invitation disguised as an accident. Deniable if he didn’t respond. Clear enough that he’d understand if he wanted to.
The handkerchief was the technology of its time. A signal that said I’m interested without the risk of having to hear I’m not out loud.
Flirting has always worked this way — a mixture of intention and plausible deniability, of being seen without being fully exposed. The note passed through a friend. The lingering eye contact. The question that isn’t quite a question. We’ve always found ways to express interest while leaving ourselves an escape route if it wasn’t returned.
The sister in the parking lot did something different. She dropped the handkerchief and then picked it back up herself. No deniability. No escape route. Just a direct question to a stranger in a parking lot.
What apps did to us
Dating apps gave us something the handkerchief never could: a way to express interest with zero risk of witnessed rejection.
When you swipe right on someone, they never know unless they swipe right too. You can want someone across a screen and never have to watch their face when they don’t want you back. The rejection still happens — it’s just invisible, algorithmically delivered, cushioned by the infinite scroll of the next option.
This felt like progress. And in some ways it was. Apps removed a real barrier for people who struggled with approach anxiety, who’d been socialized out of expressing interest directly, who’d been hurt enough times that the risk felt too high.
But something went with it.
The ability to tolerate real-time uncertainty. The practice of being seen wanting something without knowing yet if you’d get it. The muscle — and it is a muscle — of shooting your shot and being OK either way.
We outsourced the risk. And then we forgot how to carry it.
What shooting your shot actually requires
The sister in the parking lot wasn’t fearless. She was willing.
There’s a difference. Fearless implies the absence of vulnerability. What she did was full of vulnerability — she asked a stranger a direct question and had to wait, in real time, for his answer. She didn’t know if he was single. She didn’t know if he’d be interested. She asked anyway.
What that requires isn’t boldness in the swashbuckling sense. It’s a quieter thing: the acceptance that you might want something and not get it, and that the not getting it won’t break you.
The worst realistic outcome of most shots is a polite no. A quick “I’m actually seeing someone, but thank you.” An awkward moment that fades within 24 hours.
The best outcome is the story you tell your matchmaker.
How to do it in 2026
I’m not going to give you a script. Scripts are what people reach for when they’re trying to minimize risk, and minimizing risk is exactly the habit we’re trying to break.
What I’d offer instead is a mindset shift.
The question isn’t what do I say? It’s am I willing to find out?
Willing to find out if the person you’ve been talking to at the trivia night wants to get coffee. Willing to find out if the man who’s been making eye contact across the bar is actually as interesting as he seems. Willing to ask a manager in a parking lot if he’s single.
The apps trained us to curate our interest before we express it — to pre-screen, pre-filter, pre-decide. Shooting your shot is the opposite of that. It’s expressing interest before you have enough information to be sure it’s safe to do so.
That uncertainty is the point. That uncertainty is what makes it real.
The flustered detail
The manager was flustered. That’s worth noting.
He was caught off guard by a direct expression of interest from a stranger. Not because it was unwelcome — he answered honestly, after all. But because it was rare. Because most people don’t do that anymore. Because the directness of it, the humanness of it, caught him in a moment he wasn’t expecting.
That flustered quality is what the apps can’t replicate. You can’t be flustered by a notification. You can’t be caught off guard by a swipe. The surprise of being wanted, in person, in real time — that’s only available in rooms and parking lots and bars and trivia nights and anywhere else that two people happen to be in the same place at the same time.
As for the sister: last I heard, she and my friend were planning to go back to the restaurant. Sit at the bar. See what happens.
She didn’t just shoot her shot.
She reloaded.
If you’ve been waiting for the right moment to shoot yours — this is it. And if you want help finding the right room to be in, that’s what Meet Cute Club is for.
Eryn is a certified matchmaker and the founder of Meet Cute Club, a Richmond, VA-based matchmaking, dating strategy, and singles events company. As seen in Richmond Magazine.
