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Both shows are set in Chicago and Derrick, a recurring character played by Stephen Guarino, appears on both shows.Three of the original six series regulars – Casey Wilson, Ken Marino and Sarah Wright Olsen – also appeared on Happy Endings, albeit in different roles.After Jake moves into Annie's apartment, she feels the stress of sharing her space with someone and slowly begins moving into her car; Gil becomes obsessed with an all-you-can-eat buffet; Dennah tries to change her look.Annie and Jake try to set up a haunted house for the neighborhood kids in their apartment on Halloween, until their plans run afoul of "supermom" Julie; Gil and Kay use trick-or-treating as an excuse to spy on Cassie, Gil's ex-wife; Dennah tries to make a splash at a Halloween party with a very revealing costume.Meanwhile, Kay has conflicting emotions about letting go of a former love interest.The gang attends a baby shower but nobody can remember the first name of the host and they have come up with elaborate ways to hide this fact.Kay's vengeful former girlfriend takes out her anger on Jake by wiping out his identity records.Meanwhile at work, Annie has to deal with her boss, Janet (Michaela Watkins), who is impossible to please.
But when they push Gil to take charge of his life, the disruption in their relationship threatens to break the balance in their entire group of friends.
Meanwhile, Annie tries to find out what Jake's hiding from her in his desk.
Annie attempts to host the family Thanksgiving gathering for the first time, but first has to break the news to Jake's mom, Myrna, who was always in charge of hosting Thanksgiving in the past.
After Annie discovers Myrna has been flirting online with a man named Chuck (Jim Piddock), she schemes up a face-to-face meeting between them, but Myrna has reservations about getting back into the dating game because of how Jake will react.
Meanwhile, Gil attempts to throw Jake a bachelor party but things do not go as planned.