The first meeting between Steven and Whitney does not go exactly as was planned.
Songs: Dawn Landes -- I'm In Love With the Night
While the city is beset by the Puncher, a rogue criminal who punches total strangers and runs, Whitney plans her wedding. Meanwhile Laura wonders whether her friendship with Whitney can survive telling her the truth about Roy; Carlos and Mae go on a double date to a karaoke bar with Damian and Regina, and Damian realizes Mae's connection to him; and Caseman meets with his son and ex-wife and learns that there are more complications to his new life than he originally thought.
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 an unexpected situation leads to him failing.
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. Meanwhile, 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.
Whitney and Carlos are on the hunt for new apartments, and Carlos, Anya and Caseman's lives change when a friend from the past returns. Meanwhile Whitney has a rebound affair with Todd, which she struggles to keep casual, Laura meets a new man through the connecting power of the Internet, and Mae and Carlos have trouble defining their relationship -- and someone winds up getting hurt.
Laura and Whitney find themselves working on opposite sides of a hot-button political issue. Whitney's dad, developer Henry Crane, tries to raze Sedgewick's, a local landmark with significance to Laura and her late husband. Meanwhile, Caseman confides in his sponsor, Jimmy McLean, that he can't stand being alone since his recent break-up -- then finds himself reconnecting with ex-wife, Christine -- and Damian is attracted to his client's girlfriend.
Ray hires Laura and Caseman to decorate his new office space, and while working together, they figure out that they have chemistry. However, Ray learns that Caseman means more to Whitney than he originally thought. Meanwhile Damian goes to work for Ray and uses his boss' name to pull a favor for Carlos, who lands a new job, and Mae finds out about a woman who may be her mother while babysitting for Laura and Caseman.