A happy Chris begins building his cabin in the mountains near Bear Valley, only to discover a Native American artifact during the construction. The contractor stops all work until it can be verified if they're excavating sacred Indian land. Nervous that he may lose his land because of the find, Chris agrees to perform at the nearby Kahoosh Indian casino in hopes of enlisting support from his indigenous neighbors. He also wants to impress singer/songwriter Bret Michaels, who, because of an earlier misunderstanding, thinks he's selfish.
Chris's sense of civic duty is aroused when his favorite free parking spot at the public beach he frequents is suddenly designated a red zone. Chris vows to fight for the public's civil liberties and, with the support of Michelle Branch and his band, decides to run for parking commissioner – much to Yola's chagrin...
As a long-time baseball fan Chris, who often tries to meld his American boy-next-door lifestyle with his rock-star profession, revels in his newfound friendship with star Oakland A's pitcher Barry Zito. That is, until he discovers that Barry can do just about everything better than he can. He's startled by Barry's musical aptitude when he joins in on a band rehearsal, and after surfing, jogging, mountain biking, and even boxing with him, Chris wonders if there is anything Barry isn't good at. Chris tries hard to be a good sport, but is secretly frantic to find something he can beat Barry at.
After hearing about Brian McKnight's luxurious home, Chris feels pressured by the band to improve his homely house and decides to install a state-of-the-art steam room. He soon comes to regret the decision when the project begins to take on a life of its own.
Chris receives an extra $20 when he visits his local bank's automatic teller machine, and feels as though he won the lottery. But when he shares the happy news with Mona, she annoys him by insisting the money be returned. Believing he came by his windfall honestly, he refuses. Later, Chris is shocked to discover that Mona has vanished from her lair. When he runs into a girl named Stacy, who looks just like his missing muse, he wonders if Stacy is really Mona, determined to give him a morality lesson.
Chris is in for quite a jolt when Gloria Estefan arrives in San Francisco to perform with him and the band. During rehearsals she showers the guys with compliments, impressing them with her kindness and lack of pretense. Though initially flattering and supportive, the real reason for her visit is soon revealed, though not before the seeds of rebellion have been sown between Chris and the band. To make matters worse, Chris, who always shuns caffeine, is tricked into drinking Gloria's special blend of Cuban coffee, and now can't seem to function without it.
When Michael Bublé stops by to perform at Bimbo's with Chris and the band, his beautiful manager, Olivia, immediately catches Chris' eye. Though clearly attracted to one another, both initially have concerns about mixing business with pleasure. Chris shares his interest in Olivia with Yola, whose lukewarm response to the match is taken as approval by a love-struck Chris.
Chris and Olivia's relationship is going great, until he meets her good friend - and ex-husband - Neal.
Chris has a yard sale to please Olivia, because she thinks he has too much "stuff". Yola schemes to buy an elderly woman's house. Anson moves into a large RV trailer.
Chris must do some damage control when his girlfriend, Olivia, arranges for Richie Sambora to perform with him, without checking with Yola first.
Chris, Yola and the band stress out during a layover and then flight home from Wisconsin. Anson hopes to join the "Mile High Club" with a nervous flight attendant.
Chris, wanting to impress Yola with his intellect, agrees to appear on the TV game show ""Pop Whiz.""
Chris and Yola go on a romantic weekend getaway in Napa only to find his band booked there as a side gig. Anson and Tanya get back together. Cody decides to leave the talent agency