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.
A relative can attend only one wedding--either Annie's or that of her two recently engaged fathers; Gil bonds with 6th graders over laser tag and basketball.
Annie, Kay, and Dennah are able to convince Jake that Gil has become too reliant on him. Jake wants Gil to take charge of his own life but things end up changing the balance of the entire group.
The gang prepares to attend a baby shower party together and Annie and Jake consider their own family planning.
Civil war erupts when it appears that either Annie or Jake watched the season finale of their favorite program 'The Moors' without the other person - Police Officer Gary Bric performs a polygraph test to determine the true culprit.
Jake reunites with long lost friends while Gil ropes Dennah into his latest business venture.
After a rousing night out, Annie and Jake deface a sign at their building and find themselves embroiled in a hate-crime investigation in their building. Meanwhile, Gil, Dennah and Kay compete for the one remaining “plus one” spot on the wedding guest list.
Jake asks Kay for help adjusting some of Annie's annoying habits, and in return he helps Kay plan a Valentine's Day celebration for her new girlfriend; Gil and Dennah fall for some firefighters and try to track them down.
Upset after Kay breaks up with her, Brianna takes out her frustrations by wiping out Jake's identity; Gil jumps on a job opportunity at Jake's company.
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 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.
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.
