As the second season opens, six months have passed since Brian left L.A. following a fight with Marjorie. In four days, she'll marry his best friend, Adam. Now Brian is back, and Adam isn't pleased to see him. As for Marjorie, she doesn't know what to feel. Meanwhile, Dave and Deena are in therapy following their disastrous open-marriage experiment; and Nicole is about to give birth, but misses her actor-husband, Angelo, who's making a movie in Italy. Jimmy: Jason George. Ivy: Amanda Foreman.
It's Adam and Marjorie's wedding day, but she has some explaining---and soul-searching---to do over her encounter with Brian the night before. He won't let the matter drop, either. Meanwhile, best man Dave engages in some extracurricular activities with Suzanne (Marguerite Moreau) in his office; and maid of honor Nicole gets an unwanted phone call from Angelo. Flashbacks recall New Year's Eve 2003, the night Adam---and Brian---first met Marjorie.
It has been two weeks since Adam was left at the altar, and he still blames Brian for it. Meanwhile, Nicole helps Deena try to save her marriage, while Deena reciprocates by letting a nervous Nicole practice mothering by babysitting her 1-year-old. And Deena meets Suzanne (Marguerite Moreau), the woman whom Dave has been having an affair, on the set of the local cable show on which Dave and Brian are appearing to promote their new video game.
To encourage each other to get over Marjorie, Brian and Adam bet on who'll be first to get a date. Meanwhile, Brian must adjust to a new roommate: Dave (Deena kicked him out of the house); Nicole prepares for her baby shower; and Zap Monkey is in trouble, so the financially strapped Brian must get creative to save it. Michael: William Devane. Suzanne: Marguerite Moreau.
At Angelo's funeral, the friends give loving tributes and share fond memories while marveling at Nicole's strength. But they soon realize she may not be handling it all as well as she seems to be. Meanwhile, Brian's dad, Michael (William Devane), questions him about his future; Dave and Deena discuss divorce; and Adam continues to connect with Summer (Rachelle Lefevre), the stripper he met at his bachelor party.
Needing money, Brian starts a job at his father's high-end real-estate firm, where he meets a very beautiful and very successful agent (Krista Allen). Dave starts a new job as well, and he and Deena work out a unique child-custody arrangement. Meanwhile, Adam's relationship with Summer (Rachelle Lefevre) might present professional problems; and Nicole finds a way to work through her grief after losing her husband.
Adam and Heather start to second-guess their marriage; Dave suggests a way for Brian to spark the interest of the reluctant Bridget (Krista Allen); Nicole immerses herself in Deena's fledgling cupcake business to distract her from her grief; and Deena meets a rich client who might be interested in more than her cupcakes.
Brian and his dad (William Devane) are driven apart by a secret involving Bridget (Krista Allen); Jimmy runs a criminal-record check on Heather; Deena decides to go out with T.K. (Brennan Elliot) following a couple of “practice dates”; and Dave lends moral support to Nicole when he accompanies her to a screening of Angelo's last movie, where she meets a mysterious woman with a connection to her late husband.
Brian tries to avoid Bridget after he learns that she once had an affair with his father, but she doesn't make it easy. For comfort, he considers reconnecting with his mother (Patty McCormack), whom he hasn't seen in a while. Elsewhere, Brian and Adam are sentenced to community service at a homeless shelter for causing a ruckus at Ivy's bar; the very pregnant Nicole goes to extremes to induce labor; Deena has a dream date with her rich client; and Dave dates a much younger woman.
Brian and Bridget draw closer together on a company retreat; Adam wants Heather to try a new line of work following an awkward visit to her strip club with Dave; and Nicole promises Dave and Deena that they both can accompany her when she goes into labor.
Brian and Bridget talk to each other about their former relationships, but Brian doesn't mention Marjorie; Adam and Heather must deal with an overzealous ex-client of Heather's; Nicole sets up a photo shoot to promote Deena's cupcake business; and Dave and Deena make a startling discovery about their 1-year-old daughter, which brings to town a visitor from the friends' not-so-distant past.
Marjorie's return to L.A. leads to tension between Adam and Heather. It could affect Brian and Bridget as well, especially considering they have been a couple for six weeks, which is about as long as Brian has ever been able to maintain a relationship. Meanwhile, Dave and Deena spar over treatment options for Carrie; and Nic finds a male nanny (Tom Parker).
Brian invites the gang to his father's soon-to-be-sold lake house for a weekend getaway. He invites Bridget as well, in an effort to make her feel like part of the group. And during the weekend, Dave and Deena grapple with their decision about their daughter's ear surgery, while Adam tries to sort out his feelings for Heather and Marjorie.
No sooner does Bridget move into Brian's apartment than Brian, who's now the building manager, helps two attractive young women (Stacy Keibler and Jessica Szohr) move in downstairs. Meanwhile, Dave weighs the idea of moving back in with Deena to help out with their daughter's recovery from ear surgery; Nicole fantasizes about her “manny” (Tom Parker); and Adam makes a decision regarding his romantic life.
Dave's sexy, savvy and manipulative new boss, Natasha (Tiffani Thiessen), turns out to be his former (and formerly overweight) intern. And while Bridget is away on a business trip, Brian lets Laura (Jessica Szohr) and Stephanie (Stacy Keibler) use his apartment for a party. Meanwhile, the still-celibate Adam continues to pursue his law partnership; Dave and Deena sort out feelings for each other now that he's living in the guest room; and Nicole has an erotic dream about her “manny.”
Laura senses that Brian and Bridget's romance is headed for the rocks; Dave and his new “roomie,” Deena, go on their “first date,” but it's interrupted by a family emergency, one that also keeps him from the presentation he and Brian were preparing at work; Adam's boss orders him to break his vow of celibacy, and the first woman he sees after leaving his office is Stephanie (Stacy Keibler); and Nicole and her “manny” (Tom Parker) sort things out after their kiss.
Like everyone else, Deena's visiting mother (Meredith Baxter) is unaware that Dave and Deena are back together. And Brian, unattached again, gets separate invitations from his two cute neighbors. Meanwhile, Brian assigns a big presentation to Dave against Natasha's wishes; Adam and Nicole deal with the aftermath of their unexpected tryst; Dave gets into a fistfight with Deena's ex-lover; and the friends get a surprise when they visit Ivy and Jimmy's home.
After an embarrassing photo of Brian and Stephanie hits the tabloids, her manager tells her not to be seen in public with him. So Laura is secretly delighted when Stephanie asks her to accompany them to a Hollywood party and act as Brian's date. Meanwhile, Deena's new cupcake store struggles until Nicole finds a way to attract customers; Natasha sets the parameters for her relationship with Adam; and it's time for Deena and Dave to decide if they're going to sign their divorce papers.
In the second-season finale, Dave and Deena want to get away to renew their wedding vows, but their plans turn chaotic. And their daughters' babysitters, Brian and Adam, are interrupted by Natasha, who shows up with a work emergency. Brian asks Stephanie to look after the girls, but realizes he should have asked Laura when a crisis occurs. Meanwhile, Deena and Nicole's cupcake store is getting great press---leaving Nicole overwhelmed with new customers.