With a heat wave in the city, Jason and Maggie resort to lying in front of the air conditioner and watching movies all weekend, including "Trapped in a Box," their favourite Gary Busey movie...or is that a Nick Nolte film? Just as they turn to search engines to settle the argument, the power cuts out. There’s a blackout in the city and no IMDb to decide who’s right. Meanwhile, Mark has six months’ worth of frozen food from his favourite bulk store, and turns to his neighbours for ice to help salvage the defrosted meat in the middle of the blackout, but he quickly discovers that no good deed goes unpunished.
The annual trivia championships returns to the local bar, and Jason is determined to win the trophy this year. With Maggie and Mark, his team is the perfect trifecta of trivial knowledge... But neither Maggie nor Mark have any interest in playing. Mark is too busy with his new sex buddy, Shannon, who works for one of the top marketing firms in the city and Maggie wants in. Maggie insists that Mark get to know Shannon well, so she can get her own foot in the door. Helping Maggie out immediately backfires on Mark, and he gets sucked into a full-on relationship with Shannon, but with none of the sex. Maggie may want the internship Shannon has to offer, but at the cost of Mark’s happiness? Meanwhile, with Maggie and Mark both preoccupied with Shannon, Jason is forced to recruit new trivia partners, Simon and Bea, in an attempt to take home the coveted trophy.
Jason runs into a college friend who has since dropped out of school, which brings him to question his own life path. After looking at his vision board, the only plausible thing left to achieve is to perform music live. Never having heard his music, Maggie signs him up for open mic night at the bar, but then quickly regrets her decision. Meanwhile, Mark is stuck in a dry spell, unable to pick up a girl to save his life. With Jason off the market, Maggie suggests Mark get a new wingman – like Simon. But Mark quickly learns that Simon knows nothing about women.
Wanting to keep up appearances as the young, hip couple, Jason and Maggie agree to score pot for their suburbanite friends. A new job forces Mark to visit his doctor after fifteen years only to be diagnosed with scurvy.
A new girl moves into the building, putting Mark and Simon in competition to be her first contact. Jason and Maggie meet a new couple friend, but worry they might want to be more than just friends.
Jason runs interference when Mark wants revenge on a guy who humiliated him in college. Simon challenges Maggie to a day of not laughing at other people’s misfortune just before volunteering her to help arrange the funeral for one of Bea’s beloved cats.
When the question of kids comes up, Jason and Maggie don’t see eye to eye. Mark tries to teach Simon a thing or two about going to a club.
On an epic quest for brunch, hunger creates cracks in friendships and makes mountains out of molehills as Maggie wonders if Jason cares enough about what she does with her life, and Jason worries that Mark has replaced him with Simon.
Unintentionally wearing a suit causes Mark to be mistaken for a functioning member of society. Jason and Maggie decide to take the plunge and get a joint bank account, but they first have to deal with Jason’s banking history.
Mark helps Jason deal with his confrontation issues while on the search to purchase a video game. Meanwhile, Maggie’s best male friend is staying over and she questions his intentions for the first time.
Maggie deals with an emasculated Jason after he discovers he’s incapable of handy work. Mark attempts to ‘fade out’ a girl he thinks is too nerdy for him.
When Maggie’s dad comes to town, Jason and Mark vie for his attention but discover a secret he’s been keeping in the process. Meanwhile the new, hardworking waitress at the bar quickly becomes Maggie’s nemesis.
When an old friend and former neighbour is getting married, the gang goes into full wedding mode, and for Jason, that’s avoid the topic of marriage mode. Maggie has a meltdown when she has emcee duties thrust upon her at the last minute. And Mark’s past with the bride puts a snag in his plans.
