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- This Chicago-set sitcom follows the intertwined lives of six young urbanites trying to learn the ropes of adulthood. Through breakups and whatever other curve-balls life throws them, the pals stick together.
- Annie and Jake finally get engaged after six years, but her larger-than-life personality and his laid-back approach to life will severely test the theory of "opposites attract". They quickly realize getting engaged was the easy part.
- Life for a successful ladies man gets thrown for a loop when his cousin moves in.
- When Jane (Eliza Coupe) wants to plan the wedding of Penny's (Casey Wilson) dreams, Pete (guest star Nick Zano) admits that he'd rather elope.
- After returning from a romantic two-week island vacation, Jake is all set to pop the question on bended knee, but before he can ask, Annie lets loose on Jake for his inability to commit. Annie tries to make amends with a proposal of her own but the comedy of errors continues. The only thing we know for sure is that these two are destined to be together - whether they can get it together or not.
- Jake moves into Annie's apartment and she begins to feel the pinch of having to share her space with someone. She confesses her claustrophobia to her dads Kevin 1 and Kevin 2 but her stress continues to mount. Meanwhile, Gil discovers an all-you-can-eat buffet where he can eat for one low price all day - as long as he never leaves the restaurant.
- Annie and Jake plan a haunted house in their apartment for the kids in their building but their plans run afoul of a super-mom Julie. Dennah plans to make a big splash at an exclusive party in a very skimpy costume. Meanwhile, Gil and Kay go trick-or-treating and use the opportunity to spy incognito on Gil's ex-wife.
- As the gang gathers to celebrate Annie and Jake's sixth anniversary of their first date, their plans are disrupted by an epic storm and everyone retreats to the basement for shelter. Gil wows the group with his take-charge attitude, while Annie, Kay and Dennah become completely obsessed with finding out what Jake appears to be hiding in his desk.
- Annie decides she would like to host Thanksgiving dinner for the first time as a newly-engaged couple but Myrna, Jake's mom, has always hosted. While Myrna appears to be supportive of the change of plans, Annie quickly realizes that she is engaged in a complicated chess match over who will be the most important woman in Jake's life. Meanwhile, Gil goes in search of cheese to bring to the Thanksgiving dinner and discovers that he has a knack for fine cheese tasting. His newfound talents lead him to an underground world of exquisite and unique cheeses.
- After a meeting with Annie and their wedding officiant Dawn, Jake decides he should get to know Annie's dads better. When Jake and Kevin 1 bond over their love of motorcycles, however, it leads to some pretty serious family trouble, particularly with Kevin 2. Meanwhile, Gil is very excited about his booth at the annual Flemish Pride Parade and enlists Annie to help him prepare a special musical production.
- When Annie and her newly engaged dads learn that their awesome cousin "Scooby" can only attend one of their weddings, they are drawn into a subversive "bride war" over whose wedding will win out. Meanwhile, after he is stood up by Dennah and Kay, Gil bonds with a group of sixth grade boys over basketball and laser tag.
- Annie, Kay and Dennah convince Jake that Gil has become entirely too reliant on him for everything. Jake pushes Gil to take charge of her own life but the disruption in their relationship breaks the balance of the entire group. Meanwhile, Kay reveals she is having trouble letting go of an old love interest.
- The gang sets out to attend a baby shower, but nobody can remember the host's first name. Elsewhere, Annie and Jake explore their own family planning.
- Jake and Annie clash when it appears one of them watched the season finale of their favorite show without the other. Dennah enlists her cop boyfriend (Rob Riggle) and his partner (Natasha Leggero) to administer a polygraph test to determine the culprit.
- Jake and Annie recruit Kay to cure them of their annoying habits. Dennah and Gil pursue a hunky fireman.
- Annie hears that her ex-boyfriend Lee is in a coma and realises he will never find out she's engaged to somebody else. Kay sends heartfelt final messages to the gang when turbulence hits her flight.
- Gil tries to salvage Jake's bachelor party when the arrangements go awry. Annie discovers Jake's mum has been flirting with a guy online so she tries to engineer a face-to-face meeting between them.
- Gil is persuaded to do whatever it takes to win a wedding cake making contest. The unexpected return of Annie's biological mother Pam, the egg donor used by her two dads, creates family tension.
- Annie discovers that she was born in Canada and is not a US citizen. As her family and friends help her to revise for a citizenship test, Jake takes over responsibility for planning their wedding.