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.

After Annie and her newly engaged dads discover that their cousin "Scooby" can only attend one of their weddings, they battle it out over whose wedding will win out.

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 makes preparations to attend a baby shower but nobody can remember the first name of the host and they have developed elaborate ways to hide this fact. Meanwhile, Annie and Jake are considering their own family planning and their impending appointment with their fertility specialist "Dr. What's-His-Name" has put Jake a little on edge.

When Annie and Jake sit down to watch the highly-anticipated season finale of their favorite program "The Moors", they are shocked to discover that someone appears to have watched it already. Tensions mount and battle lines are drawn as they both vehemently proclaim their innocence. Dennah (Sarah Wright Olsen) volunteers her new boyfriend Police Officer Gary Bric and his partner Officer Laguna Matata to perform a polygraph test to determine the real culprit. Everyone is surprised at the results.

Annie realizes that Jake needs more groomsmen to match her nine bridesmaids and makes a concerted effort to reunite Jake with his long lost friends. Once "The Boyz" are back in their lives however, Annie finds herself competing with them over who knows Jake the best. She also learns that Daniel may be the real reason behind Jake's falling out with his friends. Meanwhile, Gil persuades Dennah to join him in his newest business venture - diet shakes.

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.