Kyle brings back an old tradition and surprises Kellie with a day full of adrenaline and bungee jumping, but Kellie's fears kick in as she climbs to the top; Kyle decides to play matchmaker for Kellie's friend, Jen.

Hilarity ensues when Kellie drives an Uber around Nashville to raise money for charity. Meanwhile, we get an inside look as Kyle works with his good friend and famous country singer / song-writer, Lee Brice.