Samantha returns to work, and a board meeting reminds her what a cutthroat workaholic she used to be. She begins to wonder whether she wants to be that way again. Tracy: Joy Osmanski. Chase Chapman: Rick Hoffman. Dr. Kegoshian: Frank Maharajh. Waiter: B.J. Clinkscales. Jerri: Dana Sorman. Vic: Jamison Haase.
Samantha goes to a friend's wedding, only to learn she's been uninvited by the bride. Valerie: Jessica St. Clair. Bridesmaid: Kara Taitz. Paul: Gerald Downey. Paul's Wife: Amanda Young. Troy: Curt Cornelius.
Sam runs into an ex-boyfriend and learns he has a restraining order against her. After some reflection, she believes that her need for constant attention is the result of a poor relationship with her dad---and she's determined to make things right.
Samantha sees a hypnotherapist in hopes of recovering lost memories, but all she gets out of it is the idea that Regina and Howard may not be her real parents. Meanwhile, her ex-boyfriend Todd makes a confession to her.
Samantha's mother sets her up on a blind date with Kevin (Eddie Cibrian), the contractor hired to refinish their floors. After she unintentionally makes Kevin think she's a big hockey fan, Sam turns to her ex-boyfriend Todd for advice. Chloe: Kiele Sanchez. Tracy: Joy Osmanski.
Samantha has to move back into the apartment when she learns that she could be evicted for subletting it to Todd. Meanwhile, Dena and Sam's mom bond when Sam doesn't show up for a makeover night with her mother. Chloe: Kiele Sanchez. Audrey Rhodes: Beth Littleford.
Sam gets a marriage proposal from the wealthy co-owner of the real-estate company (Timothy Olyphant) and doesn't know how to respond. She does know that Andrea is infatuated with him, and fears this could jeopardize their friendship. Chase Chapman: Rick Hoffman.
Sam asks a complete stranger named Craig to Todd's photo gallery show in order to prove to Todd that she's over him. But is Craig as much of a stranger as Sam thinks he is? Meanwhile, one of Todd's photos on display is a shot of Sam. Craig: Jerry O'Connell. Chloe: Kiele Sanchez.
Sam's affair with Todd continues while he's still seeing a clueless Chloe; Sam gets the idea that Regina is having a tryst of her own. Meanwhile, Andrea and Dena talk about opening up a coffee shop together.
As Season 1 closes, Samantha and Todd heat up. But she steps on the brakes until he breaks up with Chloe like he promised. The problem: Chloe keeps telling Todd about her sick aunt, and Sam thinks she's preying on his sympathy to keep from being dumped. Meanwhile, Andrea and Regina disagree on plans for Sam's birthday.