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The duo and their friends attend the wedding of one of Jill's ex-girlfriends. While guy pal Mikey sees the event as a chance to score with some lonely single women, Elisa dreads appearing as one of them.

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.

Jill's mother and Jack's parents visit the newly engaged couple at Jack's aprtment. Jack hits it off with her future mother-in-law, but Jill has lesss 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.

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.

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.

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.

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.

After a customer causes a disturbance at the bar, Dante 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.

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.

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.

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.

With just three weeks to go before Jack and Jill's wedding, issues start to pop up that reveal how little the couple has discussed life's big issues with each other.

Jack and Jill scramble to keep their wedding on track after the hurricane destroys their Bahamas plan, but the couple is in a bad place.