The KeepWOL Evolution

KeepWOL started as a simple way to engage in meaningful conversation between significant others for “at home” date nights and pillow talk. At the time, the game was simply called “the questions game” and was meant to strengthen their bond by learning new things about each other even after years of being together.

Fast-forward a few years, to when our Chief Wonderer went on a group vacation with a few friends she hadn’t seen in months. During the first couple of days there was more than enough to talk about because there was a lot of catching up to do. However, on day 3, by the time dinner came around the group was at a loss for conversation topics. Our Chief Wonderer suggested playing “the questions game.”

As people eased in, the game got good! There was lots of laughter, embarrassment, a few arguments/disagreements (shhh), and maybe even some tears! Eight hours later, the group had to actively stop the game at 4am because people had to catch flights. This group of friends learned more about each other in eight hours, than they had in their eight plus years of knowing each other.

About a month later, our Chief Wonderer was on a long commute to her day job and was Wondering Out Loud (to herself) what her passion was. Her commute was around 1.5 hours long and she would typically talk on the phone to friends or family. She did this not only to pass the time, but because she loves talking to people and getting in their business. She’s very nosy! But this day, she wanted to focus on her future. She wanted to think about how to get out of her forever long commute, as well as, figure out how to do what she truly loves for a living. It was, during that commute, on that day, January 18, 2018, that KeepWOL, LLC was born!

Our Chief Wonderer called one of her friends that had played the game with her during that vacation just one month prior to tell her about her great idea. To her surprise, her friend disclosed that she had played “the questions game” with another set of friends during a recent road trip. She said she learned a lot about them and realized that part of the excitement of the game is playing it with different people. That is when our Chief Wonderer knew she had something special on her hands! And so the KeepWOL journey continues…