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Cheryl secretly plans a reunion between Jim and his estranged sister (Jennifer Coolidge) when the family takes a trip to Las Vegas.

According to Jim

Vegas, Baby

Freeform

Cheryl's recently widowed mother (guest star Kathleen Noone) introduces her fiance to the family, drawing disapproval of the whirlwind romance.

Mom's Boyfriend

Dana pretends to be Ruby's mother to attract the attention of a single father she met in the park.

About a Girl

The household is annoyed when Gracie adopts an abandoned bird.

No Harm, No Fowl

An online bidding war reveals to Cheryl that Jim is spending money on memorabilia instead of a new dryer.

The Helmet

Jim and Cheryl's new friends turn out to be obnoxious, but they benefit from the relationship.

Deal With the Devlins

Jim must decide between helping Cheryl through surgery or meeting his hero, Bo Diddley.

Bo Diddley

Jim does more harm than good when he stands up to Dana's boss; Andy has trouble making arrangements for his birthday party.

Dana Gets Fired

A successful guy that Jim went to high school with gives him a big contracting job and makes a pass at Cheryl over dinner.

The Pass

Jim goes into protective overdrive after Cheryl is mugged while shopping.

Wonder Woman

Jim worries Cheryl will learn the truth about her engagement ring after she invites his old girlfriend (Crystal Bernard) to dinner.

The Ring

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S2 E21 | Bo Diddley

E28 | Vegas, Baby

E27 | Vegas, Baby

E26 | Mom's Boyfriend

E25 | About a Girl

E24 | No Harm, No Fowl

E23 | The Helmet

E22 | Deal With the Devlins

E21 | Bo Diddley

E20 | Dana Gets Fired

E19 | The Pass

E18 | Wonder Woman

E17 | The Ring