Sam loses big at the craps table in Vegas. But a chance meeting with her ex-boss, billionaire Winston Funk, could be the answer to her financial dilemma.

Sam becomes the head of the charity foundation for Winston Funk and hires Andrea as her vice president of legal affairs. She soon regrets this idea when Andrea shirks her duties in favor of planning her wedding.

Sam decides to give Todd a second chance by going out with him on another "first date," but Todd doesn't trust Winston Funk, believing he and Sam may continue the affair they were having before the accident. Meanwhile, Andrea appears on a reality TV series about celebrity weddings, along with her gay basketball star Tony Dane.

Samantha vaguely remembers something about Winston Funk's ex wife Gigi before the accident. Chapman tries to ask Dena to marry him. Andrea tries to lure Tony Dane into bed. Regina is caught in a love triangle as she prepares to leave on vacation with Howard.

It's Andrea's wedding day! While Andrea has chosen her life partner, Samantha has to make a decision as to who she wants to be with. Will it be debonaire millionaire Winston Funk or her not-rich-but-ever-reliable ex-boyfriend Todd. Even Sam's parents are at a crossroad as Regina and Howard begin to take separate paths.