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While visiting his parents (George Segal, Jessica Walter) in Florida, a New York executive decides to drop everything and move into their retirement community. The move prompts his parents to make an unexpected life decision as well.

Alan hits Elaine with a golf cart, but puts the blame on David. Meanwhile, David takes advantage of Elaine's empty apartment and plans a romantic dinner for Jessica.

A New York executive, decides to drop everything while visiting his parents (George Segal and Jessica Walter) in Florida, and move into their retirement community. The move prompts his parents to make an unexpected life decision as well.

All is well in David's life until his parents go head-to-head for the neighborhood board seat and take dirty politics to another level.

Alan wants a relationship with no strings attached. David must keep a secret from his father.

Alan becomes jealous as David develops a budding relationship with Elaine's new boyfriend, an astronaut (John Hurley).

In an effort to stop his mother from meddling in his dating life, David tells a lie that snowballs out of control.

David becomes the community's matchmaker and reaps the financial rewards with his number one escort, his father.

Alan sets David up with some job interviews in an effort to build his confidence, but makes matters worse when David strikes out on all of them.

Elaine and Alan battle for David's affections by buying him fancy gifts.

It's Alan & Elaine's anniversary and the newly separated couple don't know how to handle it. David decides to come clean to Jessica about his one-night stand.

Alan sets out to get Elaine back, only to find she might be seeing another man. He recruits David and Amy to help get to the bottom of things and win back his wife.

Alan and Elaine visit a couples therapist to help them explore their new relationship and they're tasked with planning the perfect date for each other. David tries living with Amy but they soon find out they're more like their parents than they think.

Elaine and Alan struggle to find the right balance of togetherness in their new relationship. When Elaine tags along with Alan on his weekly poker night, Alan finds himself stuck. Brandon helps out David when he discovers David is bluffing about a job.

On the day of Amy and Jared's wedding, Amy discovers Jared may only be marrying her to get his Green Card so he can stay in the country. When Brandon and Jared both make their true intentions known, Amy must choose between them.

David meets a girl, Jenn, but Elaine and Alan question her motives for dating David. David starts to believe his parents, until Jenn reveals the reason for her strange behavior is she's a single mother. Jared is reluctant to make a big commitment to Amy.

Amy pushes Alan to be closer with Jared. But when they become closer friends than Amy planned, it starts to take its toll on their relationship. Meanwhile, David struggles with Alan treating Jared like the son he never had.

David notices Elaine is acting strange. He discovers that Elaine has kept her apartment in secret, but that might not be the only secret she's keeping. David enlists Amy's help to get to the bottom of their mother's secret life.

After an unexpected kiss from Brandon, Amy is thrown. She questions her relationship with Jared, and everyone in the Robbins family gets involved to make matters worse. Dave and Jenn have trouble setting ground rules for their relationship.

After her breakup with Jared, Amy discovers that she's pregnant... maybe. Before she can find out for sure, the news gets out and the whole family is abuzz. When Amy learns she's not actually pregnant, she has a harder time breaking the news than expected.

Jared proposes to Amy, much to Brandon's dismay. But when Jared suggests they get married in two weeks, Brandon suspects Jared has ulterior motives. While Amy and Elaine plan the wedding, David discovers Brandon's suspicions of Jared were right.