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In the series premiere, emotionally volatile Annie flips out and goes on a tirade about her longtime boyfriend Jake's inability to commit right at the moment he's about to propose to her, insulting all their family and friends in the process.Following several more botched proposals, they finally get engaged and Annie reconciles with everyone she insulted.
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 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.Thinking their anniversary is cursed, Jake and Annie set out to celebrate a problem-free night with their friends to prove there is no curse on the night of their six year anniversary of their first date, until a massive storm hits just as they thought the curse was broken.When the storm hits, the gang moves into the basement for safety, where everyone is impressed by Gil's take-charge attitude, particularly Dennah.Meanwhile, Dennah, Gil and Kay get caught up with a pair of police officer swingers Gary Thick (Rob Riggle) and Laguna Matata (Natasha Leggero).
Dennah also enlists the help of her Gary and Laguna to perform a polygraph test to find the truth.
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.
Myrna appears to be supportive at first, but Annie eventually realizes that Myrna sees this as a competition between them as the most important woman in Jake's life.
Meanwhile, Gil discovers the strange world of underground cheese tasting.
Annie tracks down Jake's old college friends "The Boyz" when she realizes Jake doesn't have any groomsmen for the wedding.