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.
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 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, 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.
There are a lot more fish in the sea than just Marjorie, so Ivy makes a bet with Brian and Adam. Either they get over Marjorie and go out on a first date with someone new, or one of them has to pay the 0 bar tab. Deena kicks Dave out of the house and he moves in with Brian. "Zap Monkey" gets into financial trouble and Brian must figure out how to save it. Nicole has her baby shower. Brian attempts to surprise Nicole by having Angelo flown home for the shower, but tragedy strikes.
What About Angelo's Ashes? Everyone learns about Angelo Varzi's death. While at the funeral, everyone shares memories of him and remembers the good times. Nicole puts on a front making it seem like she is handling everything ok, but she breaks down. Brian goes back to his dad for help and his dad urges him to take the job offer to work for him. Deena and Dave spend time talking about getting a divorce. Adam seems to be showing more of an interest in Heather(Rachelle LeFevre).
In need of money, Brian starts working at his father's high-end real estate firm. Sparks fly when he meets the company's top agent, the beautiful Bridget. Meanwhile Dave begins a new job as well, and he and Deena work out a unique child custody arrangement; Adam's relationship with Summer may mean problems with his professional future; and Nicole moves on despite the grief after losing her husband.
Every begins to take the first steps in moving forward in their lives. Nicole tries to help Deena out with her cupcake business, but things turn interesting when Deena meets a rich client, who seems to be smitten by her. Dave tries to help Brian, who is trying to find ways to make Bridget interested in him. Dave tells him to go to a speed dating thing. He says to bring Bridget along so she could see the other jerks and then Brian would look better to her. Adam and Heather start to rethink getting married.
Everyone seems to be have their secrets. Bridget has a secret that starts to tear apart the connection that Brian and his dad are working on building. Now that Adam and Heather are married, he doesn't feel comfortable with her being a stripper anymore. He talks to Jimmy about it, who in turn runs a criminal background check on her. Dave and Nicole go to the filming of Angelo's last movie. Nicole is thrown off by a mysterious woman who is that. She seems to be connect to Angelo somehow. Deena finally gets up the courage to go out on a date with T.K.
Nicole is anxious to finally have the baby and tries every old wives tale out there to induce labor. Deena and Dave each go out on seperate dates. Deena goes out with her rich client, TK, while Dave goes out with a woman much younger than he is. Brian and Dave cause a lot of problems along with damage at Ivy's bar and they are forces to do community service at a homeless shelter. Brian is very uncomfortable with the fact that Bridget and his father had an affair, and does whatever it takes to avoid her.
When Brian's dad decides to take the real estate company away on a retreat, Brian and Bridget gradually get closer. Meanwhile, after Adam and Dave make an awkward visit to the strip club where Heather works, Adam wants his new wife to give up her job, and Nicole promises both Dave and Deena that they can accompany her when she goes into labor, but neither is willing to give up the spot to the other.
Brian and Bridget take some time to get to know each other better and talk about their Exes. But Brian isn't totally honest with Bridget, because he fails to tell her about Marjorie, who has since returned back home. Dave and Deena discover something about their one year old daughter, which leads to someone from their past coming to town. To help promote Deena's cupcake business, Nicole sets up a photo shoot. Heather and Adam are forced to deal with an old client of hers that just won't go away.
Marjorie's return causes all kinds of problems and conflicts amongst the new couples. Heather knew she was the second choice for Adam, but didn't feel like it until Marjorie came back. Brian, who normally dumps his flings around the sixth week, is celebrating his sixth week anniversary with Bridget. Nicole is on the hunt for a nanny, but she seems to find something wrong with each one of them.
Now that Brian's father must sell his lake house, Brian invites the gang there one last time for a weekend getaway. He hopes to make Bridget (Krista Allen) feel more like a part of the group of friends. Meanwhile Dave and Deena grapple with making the decision about their daughter's ear surgery, and Adam tries to figure out his feelings for Heather (Rachelle Lefevre) and Marjorie.
Now that both Brian and Bridget have lost their real estate jobs and she has lost her condo, she moves into Brian's apartment, where he has taken a job as the building manager. Brian helps two extremely attractive women, Laura (Jessica Szohr) and Stephanie (Stacy Keibler), move into the apartment downstairs. Meanwhile, Deena and Dave discuss whether he should move back home to help with their daughter's ear surgery recovery, Nicole fantasizes about Jamie (Tom Parker), her "manny", and now that he's separated, Adam takes a vow of celibacy.
Dave is surprised to see that his new boss, Natasha, turns out to be his former intern. She has re-invented herself from being overweight and non-descript into a sexy, manipulative and shrewd businesswoman. While Bridget is away on a business trip, Brian's downstairs neighbors, Laura and Stephanie, convince him to let them use his apartment for a party that turns raucous. Meanwhile, the still-celibate Adam continues to pursue his law partnership, Dave moves into the guest room back home and Nicole has an erotic dream about her "manny".
While Brian wonders if his relationship with Bridget is the right thing, Laura senses that all is not right between the couple. Natashas favoritism toward Brian becomes apparent when she asks him and not Dave - to coordinate a major presentation for some Japanese clients. Meanwhile, now that Adam has made partner, he breaks his celibacy rule and goes out on a date with Stephanie. And after Nicole and her manny, Jamie, share a kiss, Nicole no longer thinks he is gay.
Everything looks all glittery on the surface, until you look deeper. Adam and Nicole are dealing with the aftermath of their sleeping together. They promised to keep it between them, but word gets out about it. Dave finds out that Brian was named the new manager, and it could be enough to end their friendship. No one knows about Deena and Dave reconciliation, not even Deena's mother who comes for a visit. Brian is asked on two dates by both of his downstairs neighbors. He accompanies Stephanie to a movie premiere and ends up sharing a kiss with her. The gang visits Jimmy and Ivy's house for the first time.
After an embarrassing photo of Brian with fledgling actress Stephanie runs in the tabloids, she's instructed by her manager not to be seen in public with him. So Laura is secretly delighted when Stephanie invites her to go along with them to a hot Hollywood party and act as Brian's date. Meanwhile Deena's new cupcake store struggles until business partner Nicole comes up with a unique way to get more 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.
Dave and Deena's plans for a secret getaway to renew their wedding vows turns chaotic. Meanwhile, Brian and Adam's babysitting duties for Dave and Deena's daughters are interrupted when Natasha shows up with a work emergency. Brian calls on Stephanie to look after the girls, but when a crisis occurs, he realizes that Laura is the one he should have asked to help. And after Nicole and Deena's Icing on the Cupcake store starts getting great press, an overwhelmed Nicole finds herself alone and without any help to tend to the many new customers.