In the sitcom's Season 2 opener, PJ's dream trip to Italy continues when she meets up with her mystery date. And there's gale-force activity back in the Windy City: Brendan frets about changes at the radio station; Andy holds court as a corporate lawyer; and Mike beds a waitress from Crowley's, resulting in the gang being banned from the hangout.
PJ tries to find her Mr. Right by throwing a dinner party for singles. Meanwhile, Stephanie comes into publishing success when she authors a relationship-themed book; and Andy enlists the services of a comely nanny with an annoyingly healthy lifestyle.
Mike, Kenny, Brendan and Bobby compete in a contest to create the best shirt. The tight-knit boys are on pins and needles, for the stakes are high: The winner receives free drinks for a month. Elsewhere, PJ hopes to author a book about a baseball player; Andy spends long hours at his job; and Brendan sets out to become a bartender.
Nia Vardalos ("My Big Fat Greek Wedding") guest stars in this episode, in which Andy aspires to be a good-humor man by joining an improv-comedy class. Elsewhere, a gloomy Brendan grows introspective (and seeks out some medication); visa complications haunt Bobby's girlfriend; and Stephanie's book is released---but her back-cover biography is more fiction than fact. Michael McDonald also guest stars.
Rumors swirl that Andy is having an affair with his coworker (Nia Vardalos), and Andy promptly tries to prove the gossip wrong. Elsewhere, Bobby's wedding plans turn disastrous courtesy of his family; Kenny's winning romantic streak continues; Brendan temps at a mail room; and Stephanie's freshly pressed book includes obvious references to the gang.
The Chi-town boys get set to throw a bachelor party for Bobby---but who's going to pay for the big bash? Meanwhile, PJ and Stephanie attend Elsa's shower, where Stephanie's recently released book steals the spotlight. And PJ corners Andy about his relationship with Jo (Nia Vardalos).
PJ deliberates whether to embrace or ward off the romantic overtures of Bobby's brother, a reputed womanizer. Elsewhere, hectic wedding arrangements rattle Bobby; Andy and his wife attend couples counseling; and Mexican Freddy (David Pressman) makes an unforeseen visit.
The Windy City gang breezes to the luxurious ranch of Bobby's father on the weekend of Bobby's wedding. There, sibling tensions heighten between Bobby and Jack, who woos PJ. Meanwhile, Mike hits it off with an older woman (Mimi Rogers); Bobby's father proves to be a rampant flirt; and a member of the wedding party is felled by kidney stones.
Bobby's wedding rehearsal serves as the backdrop to the second-season finale. Here, Bobby chooses his "best men," and Mike learns more about Maggie (Mimi Rogers). Meanwhile, PJ works to bring bickering siblings Bobby and Jack together. All the while, PJ and her boys reflect on how Bobby's marriage may upset the status quo. Marilu Henner and Christopher McDonald guest star.