Jack wonders if she and Jill weren't meant to wed after an act of nature clouds their plans for a wedding in the Bahamas. Audrey is stalked by a man she dated once after meeting him on a game show, and Mikey and Elisa plan a singles party. Hannah: Kathryn Harrold. Emily: Lindsay Price. Mitch: A.J. Buckley. Audrey: Jaime Pressly. Mikey: Simon Rex. Elisa: Sarah Paulson.
After realizing that they have several unresolved issues, Jack gives her fiancé a list of questions to answer on topics regarding their life together as a married couple. Meanwhile, Jill learns that Dante wants to open another bar in Boston, and that he and Jack may have to move there so he can manage it. Also, Audrey agrees to a celebrity date with a game-show contestant in order to revitalize her career; and Barto confesses to Emily that he cheated on Audrey. St. Louis Cardinals player Jim Edmonds appears. Emily: Lindsay Price. Dan: Randy Becker. Mitch: A.J. Buckley. Jack: Amanda Peet. Barto: Justin Kirk. Audrey: Jaime Pressly.
Jack, giddy about celebrating her birthday for the first time with Jill, receives a note at work telling her to meet in a hotel room. But she discovers someone else waiting there for her. Meanwhile, Audrey is jealous when Russell's ex stays at their apartment after losing her own place. Kate: Amie Carey. Russell: Jeremy Garrett. Matt: Josh Hopkins. Jack: Amanda Peet. Jill: Ivan Sergei. Audrey: Jaime Pressly.
The engaged couple lose the church reserved for their wedding. They decide to marry on a sailboat in the Bahamas, but Jack worries how her mother will handle the news. Meanwhile, Audrey gives individual dance lessons to make ends meet after the money from her movie runs out; Barto goes on a date with a waitress from the bar. Emily: Lindsay Price. Adam: Josh Zuckerman. Paul: Corbin Bernsen. Barto: Justin Kirk. Audrey: Jaime Pressly. Jack: Amanda Peet.
Jack and Jill agree to premarriage counseling with a priest in order to secure the church they want to get married in. Also, Barto learns that Mikey has a rare medical condition and asks his pal to appear in one of his classes; and Audrey tries to cool her relationship with Russell. Dr. Madison: Harry Shearer. Russell: Jeremy Garrett. Father Conlin: Paul Dooley. Jack: Amanda Peet. Barto: Justin Kirk. Audrey: Jaime Pressly.
After a customer causes a disturbance at the bar, Dante (Clayton Rohner) hires a bouncer without consulting Jill or Mikey. Jack sets out to mend her strained relationship with Elisa. Elsewhere, Audrey has an embarrassing encounter with Russell, and Barto flirts with a pretty waitress at a café. Heffer: Brent Sexton. Russell: Jeremy Garrett. Peter: Ed Quinn. Mikey: Simon Rex. Audrey: Jaime Pressly. Barto: Justin Kirk.
Jack pitches an idea to her new boss for a newscast segment that she would produce and appear in; Jill and Mikey try out a karaoke machine for the bar. Elsewhere, Barto is jealous of Sarah's crowded social schedule, so he decides to pursue other women; Audrey interviews potential roommates and meets a guy who may perfect for her. Kirsten: Maggie Wheeler. Russell: Jeremy Garrett. Sarah: Chandra West. Barto: Justin Kirk. Mikey: Simon Rex. Audrey: Jaime Pressly.
Mikey has sex with a waitress during the @ Bar's grand opening, prompting Jill to suggest to his pal that mixing business with pleasure can be a troublesome proposition. Elsewhere, Jack hears an unsettling comment from Elisa's new boyfriend, and Barto wants to keep his relationship with Sarah a secret from his parents. Sarah: Chandra West. Peter: Ed Quinn. Dante: Clayton Rohner. Mikey: Simon Rex. Elisa: Sarah Paulson. Barto: Justin Kirk.
Jill is hired by a wealthy financier for a personal photo shoot, and Jill tells the tycoon that his pal Mikey is trying to buy the @ bar, but needs a business partner. Meanwhile, Audrey discovers that her movie is a theatrical flop, and Elisa is concerned about her relationship with a new man. Dante: Clayton Rohner. Peter: Ed Quinn. Sarah: Chandra West. Mikey: Simon Rex. Audrey: Jaime Pressly. Elisa: Sarah Paulson.
Jack, Jill and their friends prepare for a trip to L.A. to attend the premiere of Audrey's new movie, but Barto plans to stay in New York to study for an exam and avoid an awkward encounter with his ex. Also, Mikey sets out to purchase a bar, and he asks Barto's father to invest in the venture. Kyle Statton: Richard Hillman. Polly: Katie O'Rourke. Jonas: Stephen Macht. Louise: Jessica Walter. Barto: Justin Kirk. Mikey: Simon Rex. Audrey: Jaime Pressly.
Jill's mother and Jack's parents visit the newly engaged couple at Jack's apartment. Jack hits it off with her future mother-in-law, but Jill has less success with his in-laws-to-be. Elsewhere, Audrey is interviewed about her new movie on a local morning talk show and she reveals an embarrassing secret, while Barto uncomfortably watches on a television board in Times Square. Paul: Corbin Bernsen. Cecelia: Melendy Britt. Hannah: Kathryn Harrold. Ken: Patrick Breen. Audrey: Jaime Pressly. Barto: Justin Kirk. Mikey: Simon Rex.
Jill has a big question to ask Jack concerning their future and he frets over just how to do it. Barto and Mikey offer Jill advice on how to broach the subject. Meanwhile, Audrey and Barto try to mend their relationship by taking it one day at a time. Barto: Justin Kirk. Mikey: Simon Rex. Audrey: Jaime Pressly.
Jack, Jill and their friends attend the wedding of one of Jill's ex-girlfriends from college. Mikey sees the event as a chance to meet lonely single women, while Elisa dreads appearing as one of them. Also, Barto deals with Audrey's refusal to spend time with him upon her return from Los Angeles. Becky: Erin Daniels. Daren: Tom Gallop. Frank: Dana Ashbrook. Mikey: Simon Rex. Elisa: Sarah Paulson. Jack: Amanda Peet.