Carlos has his hands full with a case of attempted murder; Mae changes her mind about leaving New York; Laura starts her new job; Whitney worries about her wedding plans; Steven goes back to work; and Damian's lucky streak may be short-lived.
A young co-worker challenges Caseman's ability to keep work and romance separate; Laura begins to question her late husband's integrity when she receives a mysterious video; Mae reconnects with Carlos to enlist his help in a search for someone from her past, and Carlos struggles to prove his client is innocent.
Laura frets telling what she knows about Roy to Whitney, who's busy planning her big day; Damian has a revelation when he and Regina go out with Carlos and Mae; and Steven's new life clashes with his old one.
Damian reveals to Carlos what he knows about Mae and her past, but in the meantime, she prepares to run away from the place she's called home. Laura supports Whitney through her transition by attending her big work party -- a masquerade called the Monster Ball. Caseman gets a chance to prove himself as a father to Max, but and unexpected situation leads to him failing
Damian proposes to Regina but still won't be honest about his criminal past as they look to the future. Caseman finally gets a chance to spend quality time with his son, Max, but Whitney offers him the job of a lifetime, which forces him to reassess his priorities. Meanwhile, Laura receives a promotion with some big strings attached.
Laura gets her first date since her husband died. It begins well, but when she and Andrew visit a gallery opening, Laura is shocked to discover a photo that Caseman took of her weeping on her front stoop as part of the exhibit. Meantime, Whitney is horrified to learn that her ex-fiancé, Roy, has acquired one of her clients, which forces her to work with the man who broke her heart, and Carlos learns Damian's secret about the shooting.
Steven and Anya's relationship becomes strained when an old friend from Anya's past returns. Carlos and Whitney both look for new places to live with Whitney connecting with Todd, a co-op apartment owner in the building where she finds her dream home and Carlos with Lisa, his estate agent.
Damian becomes attracted to his client Karen, who's mistress to Whitney's dad Henry. Whitney and Laura find themselves on opposing sides with the closing down of an old bar 'Sedgewick's'. Whitney meets her half-sister Lisa's new boyfriend Carlos at Sedgewick's with her father where Lisa tells them she's been fired again. Whitney offers to hire Lisa but begins to regret it when Lisa steals ideas off Melanie and uses them herself for a campaign. Elsewhere, Steven admit to his sponsor that he can't stand being alone since his recent break-up and turns to his ex-wife ...
Whitney's former college friend, Ray Jones, turns up at her workplace naked and asks her to marry him reminding her of a pact they made that when they turned 35 and if neither were married they would marry each other. She later gets fired from Ralston's after a gossip columnist prints an article that she is about to set up her own company. Ray is now a very successful entrepreneur and he now also seeks out Steven to pay him back for a photograph of his wife that Steven asked him to sell years earlier. Stephen tells him he doesn't want his money but his picture back. ...
Mae moves a step closer to finding her mother Maggie who is a friend of Steven. Ray tries to manipulate Whitney but she gets her way. Ray also asks Laura to design his new building which must include a series of pictures taken by Steven - who is reluctant to do so. Ray also given Damien a series of tasks to do and along the way Damien gets Carlos an job interview with Ray's attorney's.
Ray appoints Damien as his special project manager for the new build but infuriates Whitney by bringing in a management consultant for the business. Mae continues to attend her mother Maggie's class unknown to Maggie but gets a chance to meet her at a book signing. Laura goes on a date with Will but her heart belongs to Steven and they eventually get together.
Laura is approached by Ted Weston from the Justice Department about her husband David's investigation of Ray. She goes to Ray who denies it who in turn gets his lawyers to find out what was in David's papers. Whitney and Steven grow closer which throws a spanner in the works in his relationship with Laura. Fraud charges against Mae's mother brings the press to Mae's door and she bolts and finds comfort again with Carlos. Meanwhile, Damien is having problems getting the building to code and Melanie is not helping things with her elaborate plans but it eventually gets ...