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 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.

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?

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.