Some icebreakers have their start in the world of slumber parties or drinking games. "Have you ever ... " is a popular game in both environments. It usually involves players taking turns in a circle asking one another personal, revealing and potentially embarrassing questions starting with "Have you ever..."
"Have you ever ... " is often unscripted. That means that each player who's asking a question makes up that question on the spot. The only way to make "have you ever ... " somewhat workable in a corporate setting is to have pre-written questions to choose from. This gives the activity leader some censorship before the game begins.
For the leader, the pre-game challenge is to select questions that won't lead to potentially embarrassing answers. It may be easy for most people to answer, "Have you ever jumped out of an airplane?" However, some questions could invite awkward moments among co-workers, such as, "Have you ever been arrested?"
Of course, you could just lie if the truth is too embarrassing. It's just an icebreaker, right? That could work, but what if your co-workers learn the truth later? Then, what started as a simple lie to protect your privacy turns into a reason to distrust you. Your co-workers, even your boss, might suspect you're a dishonest person who's willing to cover things up to protect yourself.
Our final icebreaker is the flipside of "have you ever ..." and it might risk even more permanent damage to your professional reputation.