Alex signs up the gang to participate in the Northside Kickball Classic tournament. However, self-appointed manager Max has difficulty bringing his players up to scratch - Dave has a history of freezing at crucial moments after an unfortunate incident during a previous game, Penny uses the tournament as an opportunity to meet good-looking guys and refuses to put on appropriate footwear, while Jane abandons her friends altogether and started playing for another team.
Brad and Jane catch up with their exes, while Dave and Alex help Max find his awesome new roommate. Meanwhile, Penny tries to hang with Pete's friends, but tries to convince Pete that her friends are more fun.
Max's (Adam Pally) vow to play a series of vengeful pranks on his friends threatens to derail a big surprise planned by Penny's (Casey Wilson) boyfriend, Pete (guest star Nick Zano). Meanwhile, Jane (Eliza Coupe) worries when Brad (Damon Wayans, Jr.) takes a new job at a kids' gym.
With the future of his new job in jeopardy, Brad enlists his friends to help save the failing kids' gym. Max's concerns over his endless texting lead him and Penny into addiction to a powerful - and illegal - cough syrup.
A hairstylist's (guest star RuPaul) gossip revives a dormant family feud between Alex (Elisha Cuthbert) and Jane (Eliza Coupe). As Dave (Zachery Knighton) looks for a new recipe to jumpstart his flagging sandwich business, his food truck is stolen.
A play Penny (Casey Wilson) has written following her failed engagement has everyone worried that she may not be over it. Brad (Adam Pally) and Alex (Elisha Cuthbert) sign on as tastemakers for a guerilla marketing firm, and then seek to cut Jane (Eliza Coupe) out of the action.
A plan to get Penny (Casey Wilson) a date backfires, landing her in a relationship with Jane's (Eliza Coupe) boorish boss (guest star Robb Corddry). Dave (Zachary Knighton) and Alex (Elisha Cuthbert) vie over how to help Max (Adam Pally) win the Mr. Super Gay Chicago pageant.
Jane (Eliza Coupe) helps Max (Adam Pally) get his life back on track in order to impress his vengeful ex-roommate (guest star Mark-Paul Gosselaar). Dave (Zachary Knighton) bets that Alex (Elisha Cuthbert) doesn't have the discipline to redeem her outstanding Groupons.
Dave (Zachery Knighton) and Penny (Casey Wilson) discover that their parents, Big Dave (guest star Michael McKean) and Dana (guest star Megan Mullally), want to adopt. Jane (Eliza Coupe) and Brad (Damon Wayans, Jr.) look to escape their friends by joining an exclusive tennis club.
Alex (Elisha Cuthbert) and Dave's (Zachery Knighton) efforts to keep their breakup under wraps threaten Jane's (Eliza Coupe) plans for the wedding of their domineering older sister (guest star Stephanie March).