"Date Gone Wrong"
"Date Gone Wrong"
A Screenplay Challenge
A Screenplay Challenge
The Challenge
A romantic dinner. A quiet café. A night full of promise.
And then everything falls apart.
Your task is to write a screenplay of a date that completely derails. Maybe it’s awkward, maybe it’s disastrous, maybe it’s catastrophic on a biblical scale. The scene should build toward discomfort, tension, or chaos.
Set the scene. Where does the date take place? A fancy restaurant? A cheap diner? A carnival ride they can’t escape?
Define the characters. What are their expectations? Who desperately wants this to work? Who is already making an exit plan?
Decide how it falls apart.
Is it a slow, painfully awkward spiral (miscommunication, bad jokes, unfortunate truths)?
Is it instant, explosive disaster (fire alarms, surprise food allergies, a waiter quits mid-shift)?
Build tension. Does the audience see the disaster coming, or does it hit suddenly like a car crash?
End with impact. The date should leave both characters changed, horrified, furious, or ready to swear off romance forever.
What does each person want out of this date—and how does it all go wrong?
How does the dialogue shift as the disaster builds?
What’s the tone—awkward comedy, tragic failure, or absolute chaos?
Does the date end immediately, or does it somehow keep getting worse?
The Mismatch – These two people should never have met. One thinks it’s true love. The other just wanted free dinner.
The Escalating Embarrassment – Spills, bad jokes, an ex showing up. Every second is worse than the last.
The “Wait, This Is a Date?” – One person thought this was a friendly hangout. The other spent three hours getting ready.
The Hidden Secret – One person is hiding something big: a double life, a massive debt, an actual criminal record.
The Worst Possible Timing – A robbery, an emergency, a surprise engagement at the next table that puts pressure on everything.
The Unexpected Guest – One of them accidentally invited someone. Or worse—their parent shows up.
The Danger Date – Someone is being followed, someone is undercover, or there is a literal bomb under the table.
La La Land (First Date Scene) – A lesson in playful tension and mismatched expectations.
Curb Your Enthusiasm – A masterclass in escalating social discomfort.
The Office (Date Night Episodes) – Awkward romance failing in real-time.