Embarrassing Questions
Mortifying, and nothing worse than that.
- Players
- 2+ players
- Length
- 15–30 min
- Cost
- Free · no signup
- Long distance
- Works long distance
Ready?
Mortifying, and nothing worse than that.
- Players
- 2+ players
- Length
- 15–30 min
- Intensity
- Sweet
Free · No signup · Nothing you answer is saved
How do you play Embarrassing Questions?
Embarrassing Questions asks for the mortifying and completely harmless stories most people have never told — the message sent to the wrong person, the teenage phase, waving at someone who was not waving back. Partners take turns telling full stories with one follow-up each, and nothing said can be used later.
How to play
- Take turns drawing and telling. Full stories, not summaries.
- No judging, and no using any of it in an argument later.
- One follow-up question each, then swap.
- Skip anything that is genuinely painful rather than merely humiliating.
- Stop while you are both still laughing.
Why couples love this game
Humiliation shared is one of the fastest ways two people get closer, which is why it works on a fourth date and on a fortieth anniversary equally. It also has the lowest possible stakes on this site — nothing here is about the relationship at all.
There is a category of story that is genuinely mortifying and completely harmless — the thing you did at fourteen, the message you sent to the wrong person, the time you waved back at somebody who was not waving at you.
Most people have four or five of these and have told almost nobody, not because it matters but because there is never a reason to bring it up.
This deck is the reason. Nothing here threatens anything; the worst outcome is that your partner knows something humiliating and will absolutely mention it again.
Example questions
- What is the most embarrassing thing you did as a teenager?
- What is the worst message you have sent to the wrong person?
- When did you last wave at someone who was not waving at you?
- What is the most embarrassing thing you have done sober?
- What is the worst thing you have called a teacher or a boss by accident?
- What is your most humiliating school memory?
The full game has 22 of these, shuffled every time you play.
Who this game is best for
- New couples
- Double dates and groups
- After something heavy
- Long car journeys
Tips to make it better
- Full stories. A summary is not a story and everybody can tell you are hedging.
- Do not use any of it later. Obvious, frequently broken.
- Skip anything genuinely painful — embarrassing and painful are different things.
- The last card is optional and everybody already knows what theirs is.
Frequently asked questions
What are good embarrassing questions to ask?
Ones with a specific story attached. "What is the worst message you have sent to the wrong person" gets a full account; "what embarrasses you" gets nothing at all.
Is this risky?
It has the lowest stakes of anything here — nothing is about the relationship. The only rule that matters is not bringing any of it up in an argument later.
Does it work in a group?
Very well. Only one card is about the two of you, and everything else is better with an audience.