Forget who gets to keep the ring - when a couple splits, the real question is, who gets to keep the friends? Alex and Dave's wedding was supposed to be the happiest day of their lives, for them and their long-time friends... until Alex leaves groom-to-be Dave at the altar. The breakup, in the words of one pal, is a "huge game changer" that will complicate everyone's lives and make everyone question their own choices.
Dave's one-night-stand with Andrea lands him in "chicksand" as the hookup evolves into a relationship he's just not ready for yet. Jane, who thinks Alex is a terrible judge of people, can't keep herself from getting involved when her sister looks for a roommate now that Dave's moved out.
Jane insists that she and Brad befriend a sophisticated couple, Dianne and Carl, but Brad resists the idea. Max and Dave can't figure out why food and other things are disappearing from their apartment. Alex confides to Max that Dave walks and eats in his sleep, but the truth is far stranger. Meanwhile, Alex starts dating a cute artist she just happens to meet hanging around Max and Dave's place.
The gang tries to convince Max to come out to his parents when the two visit Chicago and Max has to scramble yet again to get one of the ladies to pose as his girlfriend. Meanwhile Penny meets the man of her dreams, Doug. He's good looking, funny, successful...and he's got a rather infamous last name.
After a health scare, Brad's uptight dad now has a new lease on life and just wants to have fun, which Brad is having a difficult time dealing with; Penny starts to date an attractive Italian, but she can only speak his language when she's drunk; Dave and Max have fun in their apartment with dart guns.
Alex has a mouse in her apartment and asks Dave to come over and get rid of it humanely. While there, Dave falls in love with their old place. He lets the mouse go so he can spend more time there. Penny takes a Krav Maga class. Jane joins the class, is way too intense, and kicks the crap out of Penny. Max accuses Brad of being a "gay-cist".
A horror movie gets the gang to thinking about the coming "zombie apocalypse." Dave fears he's a little zombie-like in his complacency at his boring job, and shocks everyone when he announces he's quitting to follow his dream and open a restaurant. Max and super-competitive Jane square off on some silly challenges to see who could survive if the zombies took over. Meanwhile, Penny dates a hipster named Toby and finds it exhausting to keep up with his too cool friends.
Alex and Dave are forced to confront memories of their relationship when they consider removing their his-and-hers tattoos. Jane pushes Max to go out with a guy who seems a perfect match but Max resists. Brad has to deal with the consequences when he gets a waiter fired.
Alex teams up with other small business owners to fight a chain coffee store that moves into the neighborhood, but things become complicated when Max finds out he's dating the store's owner (Max Greenfield); Dave is thrilled when his favorite high school teacher Alan (Rob Huebel) is back in town. But when Penny goes out on a date with Alan, she realizes he's not as perfect as he seems, but keeps the information a secret to avoid disappointing Dave; Brad and Jane make a bet to see who can get a job by using either their charm or being prepared.
As Alex (Elisha Cuthbert) and Dave (Zachary Knighton) struggle to move past their wedding day breakup with the support of their family and friends, Jane (Eliza Coupe) fears that her marriage to Brad (Damon Wayans, Jr.) is in danger of losing its spark. And as Dave reluctantly moves in with Max (Adam Pally), Penny grudgingly agrees to attend a cooking class with Alex.
When their favorite band is coming to Chicago, Dave (Zachary Knighton) and Alex (Elisha Cuthbert) refuse to let their recent break up stand in the way of everyone seeing them together. While Penny (Casey Wilson) is excited about reuniting with Tommy (guest star Nick Thune), a Barefoot Pedaler fiddler with whom she had a one-night stand, a YouTube video of the wedding day debacle reopens Dave's emotional wounds.
Being invited to the wedding of old friend Shershow creates unexpected consequences and feelings among the group. Brad and Jane discover unsettling news about their marital status; Alex agrees to act as Dave's wingman at the wedding; Penny pretends to be engaged to Derrick; Shershow's fiancé thinks that Alex is a "wedding jinx".
Penny buys her first home, an "amah-zing" condo complete with a wine fridge and Italian marble. But will the new digs really signal "the year of Penny" and turn her life around? And, on the year anniversary of their almost-marriage, Jane encourages Alex and Dave to finally be honest with each other -- not the best of ideas.
Alex's cute line of slogan t-shirts for babies ("Put Me to Bed") become inappropriately popular with teen girls, who make her store their newest hangout. They're also in awe of Alex and Penny. Meanwhile, Jane channels her inner mom as she goes in search of her "egg daughter," the now 11-year-old girl she thinks is the result of the egg she donated in college.
Penny's perpetually optimistic mom, Dana, is in town for a singing gig at a boat show. Her enthusiasm inspires the gang, but when Penny finds out she's hiding some less-than-happy news, she decides it's time to give mom a reality check.
Jane convinces the gang to make vision boards so they can visualize their way to their dreams, only the universe isn't exactly listening; Brad has a difficult time relating to humorless boss Mr. Forristal until the guy, a car buff, flips for Max's limo; and Dave is reluctant to introduce his new girlfriend to everyone.
Jane and Brad spend a scary Halloween house sitting for friends in the suburbs, while the rest of the gang heads to a warehouse party, where their respective costumes don't quite have the effect they anticipated, especially for Alex and Dave.
When Brad hears that Jane's old sorority sister is coming for a visit, he lies and says he has a work retreat out of town, but he's actually on "staycation" in a fancy hotel in the city; Alex meets a new guy, Liam, but his dates are over-the-top; and Max and Dave make a commercial to promote the "Steak Me Home Tonight" food truck.
Angie, Max's high school girlfriend whom he dated before he figured out he was gay, moves back to town, and her arrival affects everyone: Penny is jealous of her (and then goes overboard befriending her); Alex develops her odd crush on Max; but the strangest reaction of all is from Max, who declares a "code war" when Dave and Angie date. Meanwhile, when Jane finds out Brad has a "work wife," she decides to get herself a "work husband" and sets her sights on the slightly unhinged head of Human Resources.
Jane needs a dress to wear to her charity event, but she's a little leery when Alex offers to design one for her; Penny helps a panicked Max babysit his niece and nephew; and Dave and Brad's new friendship with their oddball mailman, Drew, isn't quite what they had hoped for.
Max, desperate for cash, agrees to dress up as Santa for Penny's charity event; Jane accidentally gives housekeeper Gita the envelope stuffed with money for their big Xmas getaway to Turks & Caicos, instead of the $200 Christmas tip she had planned -- and she schemes to get the cash back.