Unable to shake the superlative, bestowed upon him in high school, JaRon sets his sites on navigating the dating world after a recent breakup. However his failure results in a victory for his roommate Max.
A date between JaRon and Barbara takes on a set of unexpected circumstances, while a game of Scattergories turns out to be more than what Max expected.
After finding out his main barber is in jail, JaRon is left trying to devise a way to get him out. When that doesn't work he is left to find a new plan; while Max and Alexa grow even closer in their relationship.
After trying his hand at acting, JaRon returns home to find something different with Max. When Alexa doesn't come clean, JaRon sets out to find out what happened to his best friend.