Jane encourages Penny to find a man and then change him to suit her expectations. Alex stages an intervention to stop Dave from his obsession with V-neck shirts.

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.

When the gang pranks Max into thinking he won a big lotto jackpot, he vows revenge when they least suspect it. Meanwhile, Brad gets a new job as a CFO, but Jane is not amused when she learns the title is Chief Fun Officer and that Brad is working at a kids' gym.

The gang is shocked when Penny rebounds from her breakup with Pete by having a torrid affair with the last man on earth they'd pick for her -- the Car Czar. To make matters worse, she's temporarily living with Brad and Jane, who end up acting like disapproving parents. Meanwhile the friends pressure Max to get a job so he'll stop sponging off them.