Team Building Gone Wrong: Funniest Stories From Reddit
Team building is supposed to bring people together. But sometimes… it does the exact opposite. We dove into Reddit to find the funniest, cringiest, and most bewildering team building stories out there, so you don’t have to live them yourself.
Whether it’s a trust fall gone horribly wrong or a karaoke session nobody asked for, these stories are equal parts hilarious and horrifying. And yes, there’s a lesson in every cringe-worthy moment. If you want safe, fun, and memorable team building, check out the 10 best virtual escape rooms for team building.
The Worst Team Building Stories: (Reddit Edition)
Cringe Social Exercises
It was technically a diversity training exercise. Everyone was given a type of greeting from a different culture (shake hands, wave, bow, etc.). I got...two kisses on the cheek. Had to walk around and give anyone you ran into that greeting. It was mortifying. I should have just pretended I got the handshake.
We had to stare into the eyes of a workmate for 3 minutes. It was awful and if this ever comes up again in the future I will walk out.
Physical Risk / Safety Hazards
Trust exercise where a person is surrounded by co-workers and has to close his eyes and let himself fall backwards so he can be caught. No one caught him and he broke his leg, somehow.
Gotta be rock climbing when a chunk of us were in our 50s, one on crutches and one in a wheelchair. Oh, yes, and one with well known vertigo.
Forced Emotional Vulnerability
We had to sit on a chair whilst our coworkers stood around us in a circle. Then 3 coworkers had to walk up to the person on the chair one by one, get down on one knee, put their hand on the person on the chair and then say one reason why they appreciated them.
We were given a little worksheet to complete. What’s your proudest moment? What does your future hold? What’s the saddest moment? When it was your turn, you had to read your worksheet to the group and explain your answers. People went DEEP - there was crying. Gravest fears were bared. I was horrified. It was so awkward.
Awkward Performances
Team karaoke. Sober. On a Wednesday afternoon.
Write a song lyric associated with the brands we represent, to the rhythm of any well-known song, and sing it in front of the bosses as a contest. Everything to be filmed. The winning team would have the honor of singing again at a later date, at another company event, with even more people watching. As you can guess, I was very happy to lose.
We got split into groups of 8, and had to create a choreographed dance to a 30 second piece of music. There were enthusiastic 25 year olds who wanted us to twerk. Worst of all, each dance was filmed and shared with the rest of the business on the intranet. I still have nightmares.
Lessons Learned
Even the worst team building activities have something to teach us:
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Avoid forcing physical risk or vulnerability.
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Include everyone, especially introverts and remote employees.
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Make participation optional when possible: bonding works best when it’s voluntary.
- Schedule team-building during work hours.
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Humor + creativity > awkward competitions or cringe performances.
Modern, Fun Alternatives
If you want to skip the cringe and still build bonds, try:
Humor-driven virtual games – where laughter sparks connections and reinforces culture.
Asynchronous activities – let people build relationships at their own pace.
Team trivia – company history, pop culture, or themed challenges.
Coffee roulette or small group chats – introvert-friendly and low-pressure socialization.
Virtual city tours or exploration games – build a connection to your company’s physical roots.
Conclusion
Team building doesn’t have to be painful. By learning from the Reddit horror stories and swapping in inclusive, fun, and creative alternatives, you can actually bring your team closer together (without the awkwardness, embarrassment, or trust falls).