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 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 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 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.