Elaine appears determined to pursue a one-night stand of her own after catching Alan in bed with Susan. Alan asks David and Amy (Marissa Jaret Winokur) to find out if their mother is following through on her threat, as he's determined to win her back.

Alan and Elaine go to couples therapy, and the therapist (Robin Givens) suggests that each plan a secret date for the other. David moves in with Amy, after the presence of both his parents in the condo begins to bother him. But Amy soon becomes bothered by David's presence.

Elaine takes part in Alan's poker games, making him uncomfortable. David begins working for Brandon's pool care business, but hurts Brandon's feelings by saying that he is embarrassed to tell his parents what his real job is. Brandon meets Amy's boyfriend Jared (John Ross Bowie), which stirs Brandon's romantic feelings for Amy even more.

David meets a nice girl named Jenn (Danneel Ackles) at the grocery store, and lies to her about his career and financial situations. Alan and Elaine become convinced that Jenn is hiding ulterior motives with regards to David. Amy and Jared agree to move in together, but after Amy gets advice from Alan about the decision, Amy scares Jared about possible marital commitments.

Amy pushes her father to be more friendly toward Jared, but later regrets it when Alan convinces Jared to move his huge massage chair into his and Amy's apartment. Elsewhere, David is annoyed when Alan replaces him with Jared on the community's softball team, even giving David's old uniform to Jared.

David becomes suspicious of Elaine's motives when he discovers that she hasn't released her old apartment yet. David then enlists Amy's help to uncover other secrets their mother might be hiding.

Amy is confused after getting a surprise kiss from Brandon, making her question her relationship with Jared. Making matters worse, the entire Robbins family gets involved in Amy's love life. Elsewhere, David and Jenn stuggle to agree on ground rules for their relationship.

Jared proposes to Amy, leaving Brandon both heartbroken and a little suspicious of Jared's motives when the wedding is scheduled in two weeks. David discovers that Brandon's suspicions have merit.

The second season concludes with Amy facing a difficult choice: She discovers that Jared wanted to marry her quickly to get a green card, while also realizing how much Brandon is in love with her.