One important rule could be that the stories should be true. This adds an element of authenticity to the game. Another rule is that if someone feels a story is too embarrassing for them to share, they can pass, but they might have to do a small forfeit like singing a short song or doing a silly dance. Also, no interrupting when someone is telling their story. Everyone should listen attentively until the end.
A good rule is to keep the stories appropriate for the group. No offensive or overly personal stories that might make someone uncomfortable. Also, limit the time for each person to tell their story, say about 2 - 3 minutes, so the game moves along.
One way is to have each player write down an awkward story from their own experience on a piece of paper. Then put all the papers in a hat. Each player takes turns picking a paper and reading the story out loud. After that, the other players can ask questions or make comments about the story.
One such game could be 'Awkward Moments'. In this game, players take turns sharing an awkward story from their own life, and then others have to rate how awkward it is on a scale of 1 - 10. Another one might be 'Awkward Story Roulette'. Each player writes down an awkward story on a piece of paper, folds it, and puts it in a hat. Then, players randomly pick a story from the hat and have to act it out without speaking. The rest of the group has to guess what the story is about.
A great adult party game around awkward stories is 'Two Truths and a Lie'. Each person tells two true stories and one lie. The others have to guess which one is the lie. Usually, the true stories can be quite awkward. For instance, you could say 'I once tripped and fell in front of my crush', 'I accidentally sent a text meant for my friend to my boss' and then make up a false story. It's a fun way to share and guess about awkward situations.
One way to make it more engaging is to set different themes for the awkward stories. For example, one round could be 'awkward first dates', another could be 'awkward encounters with celebrities' (even if made - up). You can also encourage players to use props while telling their stories. This can add a visual and comical element to the already awkward tales, making the whole game more fun and interactive.
Add a time limit. For example, in a 'Never Have I Ever' type of game, give people only a few seconds to think of their answer. This adds pressure and can make the awkward stories even more interesting. It also keeps the game moving quickly.
The main rule is that each person can only write for a short time, usually around 30 seconds to a minute. Also, you have to pass the paper immediately after you've written your part. Another important rule is that you should try to continue the story in a logical way, although it's also okay to be a bit crazy and unexpected sometimes.
For the office party left right passing game, the basic rule is to form a circle and pass an object. The person who initiates the pass has to clearly say 'left' or 'right'. Here's a story. At an office soiree, we played this game. Mark started, choosing 'left'. The item made its way around. When it ended up with Kate, she was given the task of imitating the boss. She did it so well that we were all in stitches. This game really adds a lot of fun to the office party.
Rules for this kind of icebreaker game can include: no negative comments about the stories shared. Encourage creativity in the stories. And to make it more interesting, you could have a 'judge' for each round who decides which story was the most engaging or unique. The judge can be a different person each round. This adds a bit of competition in a friendly way and also ensures that everyone puts effort into their stories.
We had a party game where we shared embarrassing childhood stories. One person told about how they accidentally wore their clothes backwards to school. It led to a lot of laughter and more people sharing their own silly memories.
Sharing such stories is inappropriate as they often involve adult and unethical content.