Freddie tries to date Rose, a girl who recently broke up with Chris. But when Chris finds out that Rose wants to get back together with her ex-boyfriend, he seeks fun revenge on Freddie by setting up an embarrassing evening for him – which includes cooking and serving the lovey-dovey couple a romantic dinner. And later, Chris and Freddie work together to try and break the couple up.

Freddie decides to override Sofia's judgement by buying Zoey an expensive phone that she wants. When they are caught, Freddie and Chris are supposed to take Zoey to a soup kitchen to teach her a lesson, but instead decide to take her to an auction that they'd been planning on going to. The real lesson is learned when Zoey makes Freddie bid a ridiculous amount of money on an item she wants, and Freddie makes her work it off at the restaurant, finally teaching her the value of a dollar.

'Tis the season for a Christmas party, so Freddie invites his neighbors in the complex to celebrate with his family and friends. But when a jealous neighbor reports to the board that Freddie is breaking the rules by having too many people living in his condo, Freddie has to get a petition signed by the majority of the tenants allowing them to stay. However, when Freddie goes door to door, he realizes his neighbors share no good will towards his family, who have not been very conscientious – but can he win them over now?

Freddie and the gang feel that something is bothering Grandma and assume it's because all of her friends have found mates. So Freddie and Chris decide to help her find a man's man, while Sofia and Allison search for their version of the perfect man for Grandma. They try to fix her up with someone but are surprised to find she may not need their help at all.

After Freddie and Chris' trip to Los Angeles to investigate whether or not Zoey's internet friend is genuine or a predator, they realize that George's son, Max, really is a kid and invite them to Chicago so that Max and Zoey can finally meet face to face. When George sees how well off Freddie is, he teases him that he's "soft," so Freddie takes him to a rowdy bar in his old neighborhood to prove he hasn't lost his edge. But when they get involved in a bar fight and end up in jail, Freddie and George realize that they've both lost their edge and don't mind being a little "soft."

Freddie and Chris return home from a night out and walk in on his niece Zoey's slumber party. Chris jumps in and helps one of her 13-year-old friends with her boyfriend crisis, while Freddie meets Kaitlyn, the mother of another girl, and they hit it off right away. But when Freddie tries to date Kaitlyn, he learns he has to win over her daughter first, which makes Zoey jealous.