Would you rather…

One of my favorite things to ask people is the classic series of “would you rather,” questions. I recently did this the other day while sitting at a dinner table with some volunteers at church, and the results were fascinating! By simply starting with questions like, “Would you rather have vanilla or chocolate ice cream?” whole worlds of conversation can be opened up!

This is an updated approach to my classic conversation starter questions, which work, but don’t always provide the most favorable results. I began this quest of building conversations back in high school, when I would approach individuals who were withdrawn in a crowd. It was my goal to get them connected and in a conversation. My first question in this series was as follows:

“What do you think about the dwindling population of lawn gnomes in our society?”

Most people had no idea what I just said, so I’d repeat myself. The question usually knocked them just off center, so I came back with a second question…

“Do you like pickles?”

As simple as that question is, it really can ignite a fire of a conversation. I have found the pickles are one thing that people are seriously opinionated on. Usually, they either love them or hate them and would love to tell you all about why they stand where they stand! I, for one, am not a fan of the food, which usually gets pickle lovers riled up. At this point, we are ready to move onto conversation number three:

“Have you ever, or have you ever known someone that has almost drowned?”

Be wary of this question, funny though it may be. If the story goes into someone that did drown, backpedal immediately into sympathy and retreat to pickles and relish. On the flipside, I have a great story to share about a time at an honors retreat when I almost drowned in a canoe accident. If this topic goes well, ask the same question again, except with the topic of electrocution (same caution applied).

It is pretty easy to see how these questions can be either a huge success, or a terrible failure. This is why I am now exploring the realms of “would you rather,” questions…two options. The one who answers chooses whether they want to share a story alongside the answer.

That being said, what are your favorite “Would you rather?” questions? Here are a few of mine:


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