Roll a D20 to determine which mishap occurs on your date!

  1. Bad Weather: The date gets caught in a sudden downpour or snowstorm.
  2. Wardrobe Malfunction: Your outfit falls apart or you spill something on it.
  3. Traffic Jam: You get stuck in heavy traffic and arrive late for the date.
  4. Ex-Encounter: You run into an ex-partner and things get awkward.
  5. Allergic Reaction: You have an allergic reaction to the food or drinks served during the date.
  6. Your Date is a Spy: You somehow find out that they were sent to spy on you.
  7. Family Emergency: You receive an urgent family call that disrupts the date.
  8. Food Poisoning: One or both of you gets food poisoning from the restaurant’s food.
  9. Mismatched Interests: You discover that you have very little in common with your date.
  10. Communicator Mishap: Your phone dies, and you can’t contact anyone or use maps.
  11. Awkward Silence: There are long, uncomfortable pauses in the conversation.
  12. Pet Problems: A pet-related emergency interrupts your date.
  13. Unpleasant Surprise: Your date reveals a shocking and unsettling secret.
  14. Overbearing Waiter/Waitress: The waiter or waitress is overly attentive and disrupts the date.
  15. Food Allergy Surprise: Your date didn’t mention their food allergies, and you accidentally order something they can’t eat.
  16. Sudden Illness: One of you falls ill during the date.
  17. Lost Reservation: The restaurant or venue loses your reservation.
  18. Miscommunication: There’s a misunderstanding or miscommunication about the date location or time.
  19. Unwanted Attention: You attract unwanted attention from strangers while on the date.
  20. Embarrassing Memory: You bring up an embarrassing memory from your past, making the date uncomfortable.

TM & © 2026 CBS Studios Inc. © 2026 Paramount Pictures Corp. STAR TREK and related marks and logos are trademarks of CBS Studios Inc. All Rights Reserved.

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