When we're young, we learn important life lessons through play and fun: A big yellow bird on TV shows us friendship; the story of a rabbit and a turtle helps us understand the importance of persistence; a singing frog teaches us about compassion because, well, it's not easy being green. This week, I noticed that even as an adult, having fun can still teach us things.

For many folks, this time of year means obsessing over one game—basketball—and worrying about their NCAA bracket. My friends are not among those folks, but not wanting to be left out, several of them came up with a Jackson March Madness Bar Bracket and invited me to join. The game works like this: The bracket is designed to determine a champion bar in town through a battle of Old School Bars vs. The New Kids. My friend S.D. is our bracket maven and handled evaluation forms we filled out after each round, dutifully tallying points awarded and narratives we wrote to determine which establishments advanced to the next round. This week, we hit up our "Elite Eight" bars, and while having a lot of fun, I took away something besides a good time with each round.

The Old School Bars had two divisions: karaoke and food-drink. The karaoke round pitted Fenian's against Ole Tavern on George Street. Lesson from this round: Don't make assumptions about someone based on appearances. As soon as you do, the 65-year-old woman you've pegged for 1960s doo-wop gets up and delivers a rendition of "Gin and Juice" that will make Snoop himself proud and receives a standing ovation. (It's a safe bet that the 20-something guys will sing "I'm on a Boat." They will. Every time.)

Also in this round, the friends I refer to as the Karaoke Kids because of their fervent dedication finally convinced me get onstage and participate, resulting in a bonus lesson: Face your fear. Not only was it fun (it's not exactly like I'm shy to begin with), but I won a free drink.

In the food and drink round, it was Julep vs. Hal & Mal's. (I know. Calling Julep Old School may be a stretch. Just go with it.) Lessons from this round were multiple. First, it is possible to fit eight people into a booth meant for six. Second, as the saying goes, make new friends, but keep the old. I hit one of the spots with new friends and the other with an old friend. Learning more about new friends was a blast, but the sense of security and comfort that comes from a shared history with an old friend is hard to beat.

Then it was time for The New Kids in the Jackson nightlife scene. You can't talk bars without covering happy hour, and in that bracket, Underground 119 faced Pi(e) Lounge. Due to my schedule, I hit those two up on my own and walked away learning that you're never really alone in Jackson. Although I might walk into a place by myself, it's inevitable that I run into someone I know and end up having a great conversation. Or, I'll just make a new friend. To put it in childhood terms, the lesson was be nice and play well with others, because then you'll always have someone to talk to.

In the final bracket, we had the newest of the new: Parlor Market and Babalu battling it out in the specialty-drink category. Here we took away a couple of pearls of wisdom. First, fresh air is good for you. Both spots offer outdoor seating, and even on a day when we were tired, getting some good old vitamin D helped everyone feel better. Second, two different drinks can share the same name (I'm looking at you, Martinez). Differences don't mean one is better or worse than the other. It does mean you need to know whom you're dealing with or you might wind up with something unexpected.

This week, we revisit the bars that advanced to the Final Four, and ultimately we'll determine our Jackson March Madness Bar Champion. But no matter the result, it's been a great game—visiting different places and enjoying lots of good company—and that makes everyone a winner.