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?

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 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 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.