Freddie and Chris take a new approach to meeting women. After a series of unsuccessful dates with spoiled rich girls, the two decide to find "down to earth" women at a laundromat in their old neighborhood. Freddie runs into Gina, a nice girl from high school, and Chris meets Krystal, a girl easily impressed by his money. But when Freddie dates the woman he and his family think could be a perfect match for him, he ends up learning more about himself than he bargained for.

Freddie is excited to learn that a top food critic will be reviewing the restaurant, but he becomes stressed when he learns that the critic is a guy he beat up in high school for taking his sister Sofia's virginity. Sofia is even more worried because she doesn't want Freddie to find out the truth about what really happened. Meanwhile, Allison gives 13-year-old Zoey a makeover.

Freddie tries to be the "cool" uncle by taking Zoey to see "The Rocky Horror Picture Show." But when Zoey tries to impress her friends by inviting them along, and his best buddy, Chris, dresses up as Dr. Frank-N-Furter, Freddie ends up with more than he bargained for. Meanwhile, Allison and Grandma are stuck at home handing out candy, so they entertain themselves with a drinking game.

Freddie and Chris have turned the restaurant into an after hours nightclub and, while Zoey is away on a school trip, Sofia decides to go out and have some fun. But the fun turns into a one-night stand for Sofia, so Freddie has to teach her the "rules of engagement" after her fourteen-year absence from the dating scene.

Freddie finds himself attracted to the beautiful woman who has opened a bakery down the street – and who is putting a serious dent into his dessert business. There's only one problem: Chris asks her out first, and seems to be really falling for her. Meanwhile, Allison decides to send her resume around to drum up job offers, with sorry results.

Freddie and Sofia's father, whom they haven't seen in twenty-four years, comes to visit from Puerto Rico for Grandma's birthday. Though they're reluctant to let him back into their lives, Carlos charms the family and wants Freddie to consider letting him move to Chicago permanently.

Freddie makes a date with a hostess from his restaurant on the same night he's agreed to watch Zoey. Luckily, Chris steps in to babysit, but when Sofia returns early, Freddie's busted. Meanwhile Freddie's wild sister-in-law, Allison, is having a breakdown after the death of Freddie's brother, Joe, so he reluctantly invites her to come live with the family until she gets herself together.