Annie is furious about Jake's inability to commit just as he's about to ask her to marry him.
Annie is stressed over sharing her apartment with Jake. Gil camps out at a all-you-can-eat restaurant.
Jake and Annie get a haunted house ready for the children in their building but run into trouble with one of the mothers. Dennah decides to wear a skimpy costume to an exclusive party.
A huge storm hits Chicago, forcing the friends to look for shelter in the basement and ruining Jake and Annie's first-date anniversary.
Annie decides to host a Thanksgiving dinner, but clashes with Jake's mother, who's always hosted in the past. Gil finds out that he has a skill for fine-cheese tasting.
Jake attempts to get to know Annie's father better. Annie helps Gil get ready for a special musical production at the annual Flemish Pride Parade.
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 prepares to attend a baby shower party together and Annie and Jake consider their own family planning.
Jake and Annie fall out over the season finale of a TV show they usually watch together. Which of them took a sneak peek?
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 is irritated by some of Annie's quirks, so he secretly enlists Kay in an attempt to modify her behaviour. In return, Jake helps Kay organise a Valentine's Day celebration for her new girlfriend.
When Kay rejects her casual date Brianna in favour of new girlfriend Hailey, Brianna takes out her frustration by using her hacking skills to wipe out Jake's identity. Gil chases a job opportunity.
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.