Freddie is torn between two women he finds irresistible and just can't choose one, try though he might. Chris suggests dating each girl to find out who is right for him. Freddie is excited about Rose, who is fun and impulsive like him, but he's also charmed by Denise's caring heart and sensitivity. However, when these women learn that he's dating both of them, will either want to stay?

Freddie has a lovely dream that The Pussycat Dolls are in his bedroom, but is sadly awakened by Grandma's nagging. Freddie helps Chris interview potential chefs for his new restaurant, and they meet the eccentric Martin and easygoing, inexperienced Spyder – whom Chris hires on the spot, over Freddie's objections. Chris has some wild ideas for his new restaurant that Freddie tells him won't work. But when Chris gets upset, Freddie realizes he has to be a supportive friend, so he buries his objections to help Chris create a restaurant that is truly his own.

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.

Chris' new restaurant is about to open, and he wants to make all the decisions himself. He refuses to let Freddie see it in advance – which drives his friend crazy. Freddie, Sophia and Allison sneak in one night and discover a rather chic and technologically advanced restaurant. Freddie's concerns are eased until he gets a panicky call from Chris when his chef quits at the last minute. Chris relents and asks his friend to cook for opening night – but can Freddie help Chris' restaurant become a success, or will everything fall apart and even put Freddie's own restaurant in jeopardy?

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 feels like he made a mistake when he stopped seeing Denise the first time, so he agrees to drive Grandma to church, hoping to run into her for a second chance. When Denise tells him that she's seeing someone else, Freddie realizes he's going to have to work to win her back. Meanwhile Rose is back in town, and when Chris reveals Freddie's true feelings for her, she feels the same. Now Freddie is torn between two wonderful women – but which one will he choose?

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 finding out that Chris used his share of Freddie's restaurant as collateral for his own failed restaurant venture, Freddie insists that Chris ask his wealthy grandfather, Carl, for money to pay off the debt. Carl is displeased with Chris' slacker lifestyle and impressed with Freddie's work ethic, so he makes Chris work as his chauffeur to teach him a lesson about money and responsibility. When Chris feels humiliated, he pushes back, and the result is that grandfather pays off the loan but takes Chris's trust fund and condo in return. So Chris ends up homeless at Freddie's already crowded apartment.

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.

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 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 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.

In an attempt to kiss up to Dr. Celia Adams, the beautiful dean of her medical school, Sofia suggests that Freddie's restaurant be the location for a fundraiser. Freddie turns on the charm to Celia, leading to them sleeping together. While at first upset, Sofia becomes amused when she concludes that Celia is only using Freddie as a 'boy toy.' When she happily shares this with Freddie, and also tells him that he is way out of his league, Freddie is determined to prove her wrong.

Freddie feels a lot of pressure from Grandma to settle down, so he begrudgingly agrees to have a Catholic singles mixer at the restaurant to please her. There he's happily surprised to meet Denise, a beautiful young woman that Grandma hand picked for him. The only problem is, Denise is a virgin and is waiting to meet the right man – but is Freddie the one?

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 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 and Chris are both nominated as finalists for the title of "Chicago's Most Eligible Bachelor." They invite the other nominees to the restaurant for an informal get together and team up to scope out the competition. But, when they realize that only one man will be featured on the cover of a magazine, they become highly competitive and try to out-do one another to win.

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 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 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 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.