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.
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.
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 reunites with long lost friends while Gil ropes Dennah into his latest business venture.
Jake and Annie fall out over the season finale of a TV show they usually watch together. Which of them took a sneak peek?
The gang prepares to attend a baby shower party together and Annie and Jake consider their own family planning.
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.
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.
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.
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.
A huge storm hits Chicago, forcing the friends to look for shelter in the basement and ruining Jake and Annie's first-date anniversary.
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.
Annie is stressed over sharing her apartment with Jake. Gil camps out at a all-you-can-eat restaurant.
Annie is furious about Jake's inability to commit just as he's about to ask her to marry him.
