Charlie and I are excited to have you hear for our Would You Rather Challenge: March 10, 2026. This challenge is brought to you from the children’s book by The Ultimate Book of Would You Rather Questions: 1001 Family-Friendly Challenges for Kids, Teens and Adults by Kimberly McLeod.
My family used this children’s book when #Homeschooling Charlie for free reading time and also in his Creative Writing Class. Now we use the questions at night at dinner to get conversation flowing. I also share the question on my social sites, and you can do the same.
Would you rather wear the same shirt every day for a year or the same pants every day for a year? Why?
I don’t have to ask Charlie this question because he has had the same Hoodie and pants on forever it seems. Even though he has a closet full of clothes he never wants to wear anything else. Does it drive me crazy?
Yes, but as a mom we have to pick our battles and if wearing the same clothes every day is what Charlie chooses to do, I will deal with it because it’s much better than fighting and arguing and the drama it would cause asking Charlie to change clothes.
As for me you would think I wear the same pants all the time because all I wear is black slacks, but I change pants and shorts every day as well as shirts. If I had to choose, I would pick wearing the same pants every day because I love being able to pick out different shirts every morning.
As for David he has to wear black jeans and a black shirt and black shoes to work every day and on his days off he does the same thing. Except he likes to pick out T Shirts to wear on his day off so he said the same pants every day because he would be dressed for work and wouldn’t be late.
Would you rather wear the same shirt every day for a year or the same pants every day for a year? Why?
Thank you,
Glenda, Charlie and David Cates
