That One TimeA Pettigrew Lab app
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That One Time

Story prompts for the stories you already have

The best conversation starter isn’t a question off a list. It’s a story that happened to you. These 32 prompts are the ones the app uses to shake them loose.

Why a story beats a question

A question from a list puts the work on the other person. They have to come up with something on the spot, and half the time they shrug.

A story does the opposite. You go first, it’s short, and it hands everyone else a way in. Tell the one about the worst meal you ever ate and somebody at the table has a worse one. That’s the conversation.

32 prompts that pull up a story

Read one, give it ten seconds, and see what comes back. Most people have a story for more of these than they’d guess.

Yours

  • The worst meal you ever ate
  • A time you got completely lost
  • The strangest job you ever had
  • Your most embarrassing moment that you can laugh about now
  • A trip where everything went wrong
  • The time you were sure you were right, and weren’t
  • The best advice you ever ignored
  • A car that broke down at the worst moment
  • Something you did as a kid that you got away with
  • The worst haircut you ever had
  • A time a stranger surprised you
  • Your first day at a job
  • An animal that made your day chaos
  • The weirdest thing you ever found

The family’s

  • The trip the whole family still talks about
  • Something your kid said that you never want to forget
  • What you were like at their age
  • The time someone locked the keys in the car
  • A holiday dinner that went sideways
  • How your parents met, the version they tell
  • A family recipe that went wrong
  • The day a pet did something nobody could believe
  • A game night that got out of hand
  • Something a grandparent used to say

The people around you

  • The funniest thing a coworker ever did
  • A time a plan fell apart and worked out anyway
  • The worst weather you were ever caught in
  • A wedding moment nobody planned
  • The time you met someone famous, or almost did
  • A mistake at work that taught you something
  • The best prank you ever saw
  • A time you said yes and it turned into a story

How to use them

Don’t try to come up with a story for every one. Read down the list and stop at the first one that makes you smile. That’s the one you’ve got.

Then write down the first line, right away. Not the whole story, just enough that future you knows which one it is. “Sam got stuck in the mud” is plenty.

Do that a few times and you’ve got a deck. The next time dinner goes quiet you’re not reaching for a list. You’re reaching for your own stuff.

Questions

What’s a good conversation starter?
One that gets the other person talking. A short story of your own does that better than a question, because it goes first and gives people something to answer with. “The worst meal I ever ate” gets a better reply than “What’s your favorite food?”
How do I stop running out of things to say?
Keep a few stories ready before you need them. The trouble usually isn’t that you have nothing. It’s that the good one won’t come when the table goes quiet. Write the first line down when it happens and it’ll be there later.
Are these the prompts the app uses?
Yes. These are the 32 prompts That One Time shows while your list of stories is still short, in the same three groups.

Write the first line down

That One Time keeps your stories on your phone, one line each, and deals you one when the table goes quiet. $0.99 once, no account, no ads. It’s in review with the stores now.

Tell me when it’s out

More ways to never run out of things to say

  • Funny stories to tell
  • Family dinner questions
  • How to keep a conversation going
  • That One Time, the app
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