Jane is tasked with planning the perfect wedding for her older sister, Brooke (Stephanie March).
Dave (Zachery Knighton) and Penny (Casey Wilson) discover that their parents, Big Dave (guest star Michael McKean) and Dana (guest star Megan Mullally), want to adopt. Jane (Eliza Coupe) and Brad (Damon Wayans, Jr.) look to escape their friends by joining an exclusive tennis club.
Jane (Eliza Coupe) helps Max (Adam Pally) get his life back on track in order to impress his vengeful ex-roommate (guest star Mark-Paul Gosselaar). Dave (Zachary Knighton) bets that Alex (Elisha Cuthbert) doesn’t have the discipline to redeem her outstanding Groupons.
A plan to get Penny (Casey Wilson) a date backfires, landing her in a relationship with Jane’s (Eliza Coupe) boorish boss (guest star Rob Corddry). Dave (Zachary Knighton) and Alex (Elisha Cuthbert) vie over how to help Max (Adam Pally) win the Mr. Super Gay Chicago pageant.
A play Penny (Casey Wilson) has written following her failed engagement has everyone worried that she may not be over it. Brad (Adam Pally) and Alex (Elisha Cuthbert) sign on as tastemakers for a guerilla marketing firm, and then seek to cut Jane (Eliza Coupe) out of the action.
To prove how well she and her fiancé Pete know each other, Penny (Casey Wilson) challenges her friends to a couples’ game night. A job offer at a brick and mortar restaurant leads Dave (Zachary Knighton) to seek a psychic’s advice.
As Dave (Zachary Knighton) squares off against a competitor’s food truck, Max (Adam Pally) falls in love with the rival’s son. Jane (Eliza Coupe) and Alex (Elisha Cuthbert) disagree over inviting Penny’s (Casey Wilson) father to her wedding. Guest starring Andy Richter and Alex Quijano.
A hairstylist’s (guest star RuPaul) gossip revives a dormant family feud between Alex (Elisha Cuthbert) and Jane (Eliza Coupe). As Dave (Zachery Knighton) looks for a new recipe to jumpstart his flagging sandwich business, his food truck is stolen.
In order to get good basketball tickets, Max (Adam Pally) avoids telling a woman who’s interested in him that he’s gay. Alex’s (Elisha Cuthbert) efforts to be smarter pose a threat to Dave (Zachary Knighton) and Jane (Eliza Coupe). Guest starring Abby Elliott.
With the future of his new job in jeopardy, Brad (Damon Wayans, Jr.) enlists his friends to help save the failing kids’ gym. Max’s (Adam Pally) concerns over his endless texting lead him and Penny (Casey Wilson) into addiction to a powerful – and illegal – cough syrup. Guest starring David Alan Grier.
When Jane (Eliza Coupe) wants to plan the wedding of Penny’s (Casey Wilson) dreams, Pete (guest star Nick Zano) admits that he’d rather elope.
Max’s (Adam Pally) vow to play a series of vengeful pranks on his friends threatens to derail a big surprise planned by Penny’s (Casey Wilson) boyfriend, Pete (guest star Nick Zano). Meanwhile, Jane (Eliza Coupe) worries when Brad (Damon Wayans, Jr.) takes a new job at a kids’ gym.
Brad (Damon Wayans, Jr.) looks to avoid dinner with Jane’s (Eliza Coupe) college ex, until he learns that it’s a woman. Dave (Zachary Knighton) and Alex (Elisha Cuthbert) are smitten with Max’s (Adam Pally) mysterious new roommate; Penny (Casey Wilson) joins her new boyfriend’s circle of friends.
When Alex (Elisha Cuthbert) convinces her friends to join her store’s kickball team, Dave (Zachary Knighton) must face his traumatic memory of accidentally kicking a ball at Penny’s (Casey Wilson) face. Meanwhile, the ruthlessly competitive Jane (Eliza Coupe) joins a competing team in order to have a better shot at winning.
A singer celebrity buys a dress at Alex’s store and Penny positions Alex’s store as a popular place to shop. Max feels he’s dated all the single gay guys so Jane and Derrick help him meet new men. Dave tries to help Brad do a home repair and in the process Brad realizes he’s ready to get back into the workforce.
Penny and Brad struggle to cover their role in the accidental death of Alex’s racist pet parrot. Jane and Dave vie to be matchmakers for Max.
Max asks Jane to help him get his act together so he can prove that his life is not pathetic; Alex tries to use a stockpile of coupons.
Penny writes a play as a way to deal with her breakup with Pete and wants Derrick and his theater group to stage it; Alex and Max get an offer from a marketing group.
Penny's friends are shocked when she has an affair with the Car Czar (Rob Corddry); Max enters a pageant with Dave and Alex as his coaches.
When Penny's mom and Dave's dad decide to adopt a baby together, Dave and Penny react irrationally.
Jane plans her sister's wedding.
Arthur Ashy vs. John Mac & Cheese.
Introducing the Car Czar.
Alex and Dave will begin dating again, trying to "keep it cazsh." But since the last time these two got together did not end well, who knows how far the romance will get this time? While "the year of Penny" is over (and was less than "ahmahzing"), Penny will continue to date and might finally find a steady boyfriend. Brad, once the biggest breadwinner of the group, was fired from his job in last year's season finale. He'll turn to Max for tips on surviving underemployment. He'll try out a variety of jobs to make ends meet, including working on a bar mitzvah hype team with Max. Max will also keep looking for the right guy, but his road to romance won't be easy either, and even kind of dangerous when he develops a crush on a physical therapist -- with hilarious consequences for Penny.
Jane gives Max a makeover.
Laying down the law on Penny's new man
For years, perfect couple Dave and Alex drew their friends in and held them together. Now that they've split, does this group have the stuff to stay together? Or do Max, Brad, Jane and Penny have to choose sides? Suddenly every event is a negotiation... like, who gets to go on the annual ski trip? There are a lot of big questions to be answered, but this group has been together so long, somehow, little by little, they'll figure out how to hold on, even though their center is split up. It helps that Dave and Alex have agreed to stay friends. But there will definitely be other complications down the road. Happy Endings stars Elisha Cuthbert (24) as Alex, Eliza Coupe as Jane, Zachary Knighton as Dave, Adam Pally as Max, Damon Wayans, Jr. as Brad and Casey Wilson as Penny.