Serial monogamist Brian O'Hara hits his mid-30s and suddenly realizes he's the last bachelor standing in his circle of friends. Not averse to the happily ever after his friends have achieved, Brian wonders whether he'll ever find Mrs. Right. The fact that he's in love with his best friend's girlfriend doesn't help his chances.
Six months have passed since Brian left town following a heartbreaking blow out with Marjorie, the current love of his life -- who also happens to be engaged to Brian's best friend, Adam. Dave and Deena, have been suffering the fallout of their disastrous experiment with an open marriage. Meanwhile Brian's sister, Nicole, is thrilled to finally be pregnant, but unfortunately she's doing most of the nesting alone, since her husband is off in Rome starring in his first film.
On the day of Marjorie and Adam's wedding, Brian struggles with his feelings for Marjorie while Adam confronts her about the past. Meanwhile, as everyone prepares for the wedding, best man Dave makes time to meet with Suzanne, a colleague he had an affair with; and Nicole, anxiously awaiting husband Angelo's imminent return from Rome, is determined to get Marjorie the veil she ordered.
Two weeks after Adam has been left at the altar, he still blames Brian for what has happened. When their friends finally try to bring them together, they end up coming to blows. Nicole helps Deena try to save her disintegrating marriage, while Deena reciprocates by letting a nervous Nicole practice mothering by babysitting her one-year-old. Meanwhile, when Brian and Dave go on a local cable program to promote their videogame, Dave is on edge when Deena and Suzanne -- the woman he's been having an affair with -- both show up on the set and meet for the first time.
To encourage each other to get over Marjorie and back out in the dating game, Brian and Adam bet to see who can get a girl first. Meanwhile, Brian adjusts to having Dave as his new roommate after Deena kicks him out of the house for having an affair; Nicole prepares for her baby shower, as well as a surprise guest; and the future of Zap Monkey is in jeopardy, which causes a financially-strapped Brian to try anything and everything to save the company.
At Angelo's funeral, the friends give loving tributes and recall fond memories of Angelo while they marvel at Nicole's strength. However, they soon realize she may not be handling this as well as she seems to be. Meanwhile, Brian's dad, Michael, confronts Brian about his plans now that Zap Monkey has folded, Dave and Deena discuss getting a divorce, and Adam continues to connect with Summer, the stripper he met at his bachelor party.
Needing money, Brian starts a job at his father's high-end real estate firm. Sparks fly when he meets the company's top agent, the beautiful Bridget. Meanwhile Dave starts a new job as well, and he and Deena work out a unique child custody arrangement; Adam's relationship with Summer may be problematic for his professional future; and Nicole finds a way to work through her grief after losing her husband.
The group finds out about the shocking marriage of Adam and Heather, while the newlyweds try to decide if they did the right thing. As a way for Brian to forge a romantic connection with a reluctant Bridget, Dave suggests that he get her to participate with them in a speed dating event at Ivy's bar. Meanwhile, Nicole immerses herself in Deena's fledgling cupcake business to distract her from her grief, and Deena meets a rich client who might take more than just a business interest in her.
Brian and his dad, Michael, start to connect, until a secret involving Bridget drives them apart again. When Adam has trouble adjusting to Heather's ongoing job as a stripper, Jimmy runs a criminal record check on her. After a couple of "practice dates," Deena decides to go for the real thing with the wealthy T.K., her first cupcake client. Meanwhile, Dave goes along with Nicole for moral support to a screening of Angelo's last movie, where she meets a mysterious woman with a connection to her late husband.
Brian tries to stay away from Bridget once he learns that she and his father once had an affair, but she's not making it easy. For comfort, he considers reconnecting with his mother, whom he hasn't seen in a while. Meanwhile, Brian and Adam are sentenced to community service at a homeless shelter to pay for the damage they caused at Ivy's bar; the very pregnant Nicole goes to some humorous extremes to induce labor; Deena goes on a dream date with her rich client, and Dave goes on a date with a much younger girl.
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 have the conversation about their ex-relationships, but Brian doesn't include Marjorie. Adam and Heather have to deal with an overzealous ex-client of Heather's, and Nicole sets up a photo shoot to promote Deena's fledgling cupcake business. Meanwhile, Dave and Deena make a startling discovery about their one-year-old daughter, which brings to town a visitor from the friends' not-so-distant past.
Marjorie has returned to Los Angeles to help Dave and Deena treat the hearing loss of their one-year-old. Her arrival causes tension between newlyweds Adam and Heather, and coincides with Brian's six-week anniversary of being with Bridget -- a time when he traditionally dumps his girlfriends. Meanwhile, Nicole has trouble finding the right nanny until Deena introduces her to the very capable and handsome Jamie.
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 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 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 and Stephanie, 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, 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. Natasha's 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.
Deena's mother, Frankie, comes for a visit and, like everyone else, is unaware that Dave and Deena are back together. Now that Brian has broken up with Bridget, he gets separate invitations from his two attractive downstairs neighbors. Meanwhile, against Natasha's wishes, Brian assigns a big presentation to Dave; Adam and Nicole deal with the aftermath of their unexpected tryst; Dave gets into a fist fight with Deena's ex-lover; and the friends get a surprise when they visit Ivy and Jimmy's home 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.
