Happy Endings

Alex and Dave, after calling off their wedding at the last minute, find themselves navigating the complicated dynamics of remaining friends with their shared social circle.

Dave starts to realize he may be more committed to his casual fling than he intended, while Jane assists Alex in searching for a new roommate.

Jane tries to connect with a more refined social circle by befriending a sophisticated couple. Meanwhile, Max and Dave investigate strange disappearances in their apartment. Alex begins a new relationship with an artist.

Max considers coming out to his parents with the support of his friends, while Penny begins a promising relationship with a new love interest.

Brad struggles with his father's positive medical results and the change in his outlook, while Penny finds herself drawn to an Italian man she can only talk to when she's under the influence.

Brad tries to set up a co-worker with someone, Penny has second thoughts about inviting Jane to her martial-arts class, and Dave's help with Alex's odd jobs causes his friends to misinterpret his intentions.

Dave unexpectedly quits his job and announces plans to open a restaurant, surprising those around him. Meanwhile, Jane and Max compete in a series of lighthearted challenges, and Penny struggles to keep up with the demands of her new boyfriend's social circle.

Dave and Alex deal with the emotional and practical consequences of their matching tattoos from their past relationship, while Jane becomes concerned that Max has not found the romantic connection she believes he deserves.

Alex faces competition from a large coffee chain opening nearby, while Dave encounters his former high school teacher.

Penny grows uncomfortable with Alex's frequent "girls' night out" gatherings, while Max encourages Dave to take revenge.

A group's plans for a night of live music take an unexpected turn when complications arise.

An old friend's wedding takes an unexpected turn when the bride becomes convinced that Alex is bad luck, while Penny and Derrick create a fake engagement to navigate the situation.

Alex and Jane's competitive relationship reaches a new level of tension. Dave begins a relationship with a charming but eccentric woman. Meanwhile, Penny is assigned an assistant to help with her work.

Alex and Dave commit to being more honest in their relationship. Meanwhile, Penny moves into a new condo and embraces an optimistic outlook for the year ahead. Max grows concerned when Brad begins spending less time with him.

Alex finds unexpected success when his line of children's T-shirts gains popularity among teenagers. Jane begins a search to locate a child she believes was born from an egg she donated in the past. Meanwhile, Max starts a new job working at Dave's food truck.

Penny's mother, Dana, visits and initially impresses with her positive demeanor, but Penny soon discovers that her mom is concealing troubling news, prompting her to intervene. Meanwhile, Max helps guide tourists around the city in his new limousine, assisted by Brad and Jane.

Jane encourages Penny to create a vision board to help achieve her goals, but the process proves more complicated than expected. Brad struggles to connect with his strict boss until a chance encounter with Max's limo changes his perspective. Meanwhile, Dave hesitates to introduce his friends to his new girlfriend.

Penny, Max, Dave, and Alex attend a Halloween party at a warehouse, only to find that their costumes do not go over as expected. At the same time, Jane and Brad spend their Halloween looking after a house for friends in the suburbs.

Brad pretends to be away for a work retreat to avoid meeting Jane's ex-sorority friend, while actually enjoying a luxury staycation. Meanwhile, Penny grows jealous as Alex rekindles a connection with her ex, Liam, and Max and Dave create a promotional ad for their food truck, "Steak Me Home Tonight.

Max's return to his high school girlfriend Angie stirs up jealousy in Penny, his former college girlfriend. At the same time, Alex develops unexpected feelings for Max, and Dave's new relationship with Angie leads Max to start a "code war." Meanwhile, Jane discovers Brad's "work wife" and decides to find a "work husband" of her own.

Jane is hesitant when Alex volunteers to design a dress for her charity event. Meanwhile, Penny steps in to help Max care for his niece and nephew, and Dave and Brad find their new friendship with their eccentric mailman, Drew, becoming more complicated than expected.

Max agrees to dress as Santa for Penny's charity event. Jane mistakenly gives the housekeeper an envelope containing money meant for a Christmas vacation instead of a small holiday tip. Dave decides to use up all the homemade gift coupons he has collected from previous Christmases.

Dave is caught off guard when his therapist begins a relationship with Penny. Meanwhile, Max and Jane argue over a sweater, escalating into an unusual contest, and Alex and Brad form a connection through a common hobby.

Dave's father visits with his new girlfriend, who is revealed to be Penny's mother, Dana. Meanwhile, Alex adopts a parrot that proves to be more problematic than expected, and suspects the nearby Chinese restaurant is covering up illegal activity, enlisting Brad and Max to help investigate.

Jane pushes Penny to pursue a relationship and mold her partner to her ideals, while Alex tries to help Dave overcome his fixation on wearing V-neck shirts.

Penny considers ending a new relationship, while Dave worries his girlfriend may leave him. Alex ventures into a dangerous part of town in search of a party, and Brad's plans for a romantic evening with Jane are ruined by a disastrous dental emergency. Meanwhile, Max picks up a couple in his limo and is surprised to find his ex-boyfriend Grant among them.

Max begins to doubt his worthiness after his friends, except for Dave, are captivated by Grant, whom they consider perfect. At the same time, Dave becomes determined to show that he is more appealing than Max's new romantic interest.

The friends anticipate Brad and Jane's annual "Spring Smackdown," a dramatic domestic argument that signals when Max will emerge from hibernation and winter will finally end.

Dave turns his food truck into a popular destination by obtaining a liquor license, but his coworkers begin to distance themselves when they experience strange side effects from his signature drink.

Alex, in a state of panic, turns to Jane to help erase Dave's memory of an event using a family tradition known as "The Kerkovich Way," while Penny and Max aim to outdo a seemingly flawless couple in a local race and scavenger hunt.

The gang grows convinced that Penny's birthday is cursed after a series of misfortunes occur each year on the day.

Dave faces harassment from Corey at the gym and turns to his former bully, Alex, for guidance on defending himself. At the same time, Jane's strict leadership as HOA president at Brad and Jane's condo leads to growing dissatisfaction among residents, who begin to challenge her for the position.

Penny's small lie to avoid dealing with an annoying childhood friend leads to unintended complications. Meanwhile, the brothers' lonely and jealous landlord develops feelings for Alex.

The gang attends the wedding of Derrick and Eric, where various subplots unfold as characters deal with personal challenges. Brad has trouble confiding in Jane, who helps Eric scale back an expensive reception, while Max prepares to perform with his former Madonna cover band. Penny, initially upset about attending without a date, meets a potential romantic interest named Chris through Skype.

Dave and Alex rekindle their relationship, while Max cares for Penny after a severe accident leaves her in a full-body cast, though his growing attraction to her physical therapist leads him to sabotage her progress. Meanwhile, Brad struggles to keep a secret from Jane.

Dave and Alex struggle to decide on a new apartment, frustrating their real-estate agent, while Jane goes to great lengths to help Penny find a car. Meanwhile, Max demonstrates the challenges of a cashless lifestyle to unemployed Brad during a day out in Chicago.

Max gains popularity as a lively Bar Mitzvah emcee and invites Brad to join him in the business, though complications arise. Meanwhile, Dave and Alex work to appreciate and nurture their relationship.

The gang reunites for Thanksgiving by watching an old, never-before-aired episode of "Real World" in which they appeared during their college years, leading to the revelation of surprising and long-buried secrets among them.

Penny begins a tentative romance with Pete, but her efforts to conceal her concussion-related helmet complicate their connection. Jane attempts to gain acceptance at the car dealership by using Brad as a "trophy wife," while Max and Dave confront unresolved feelings tied to their past after their fist bump goes awry.

Jane struggles to craft a humorous toast for her father at the family's 20th anniversary celebration for their mattress business, while Alex confides in Dave that her parents don't know she and her ex are back together. Meanwhile, Max seeks a new best friend now that Penny is busy with her relationship.

The gang learns that Jane's birthday is on Christmas and that she prefers it not to be overshadowed by the holiday. They decide to throw her a birthday party that focuses entirely on her, without any Christmas themes.

Brad and Penny accidentally break one of Alex's cherished childhood items and attempt to fix it, only to make things worse. At the same time, Jane and Dave go overboard in their efforts to find a romantic match for Max.

A pop star's unexpected visit to Alex's store leads to a publicity stunt orchestrated by Penny. Meanwhile, Max explores his identity with help from Jane and Derrick at Chicago's themed gay bars, and Brad and Dave attempt to embrace traditional masculinity by tackling home repairs.

Alex enlists the group to compete in the Northside Kickball Classic, but team manager Max struggles to keep the squad focused and prepared. Dave suffers from performance anxiety, Penny is more interested in socializing than playing, and Jane unexpectedly switches teams.

Brad is surprised to discover that Jane's ex, Ryan, is a woman when she visits town, while Max's new roommate, Chase, impresses everyone with his luxurious upgrades to the apartment. However, when Chase abruptly vanishes, the group becomes curious and begins investigating his personal life.

The gang tricks Max into believing he has won a large lottery prize, prompting him to plot revenge at an unexpected moment. Meanwhile, Brad starts a new job as CFO, though Jane is unimpressed to learn the role is actually Chief Fun Officer at a children's gym.

Jane tries to convince Pete not to elope with Penny by taking the group to a wedding expo, where different subplots unfold as Max and Brad explore the gay-marriage section and Alex and Dave confront their own relationship anxieties.

Brad works with his friends to support Chuckles and Huggs as the gym faces possible closure due to its eccentric owner Terry's announcement. At the same time, Penny and Max attempt to stop texting the men in their lives.

Max pretends to be straight after meeting a charming Bulls season ticket holder, while Alex tries to prove she's more than a "ditzy blonde" by educating herself, disrupting the usual group dynamic.

Max consults the sisters' longtime hairdresser, Krisjahn, and overhears juicy gossip, but his inability to keep secrets threatens to ignite a major conflict between Jane and Alex. At the same time, Dave and Penny investigate the theft of the Steak Me Home food truck, trying to uncover who is responsible.

As her wedding approaches, Penny reconnects with her estranged father, Roy, in a tense but heartfelt encounter, with mixed reactions from her friends. Meanwhile, Dave tries to undermine his rival "The Brazilian" food truck with help from Brad and Max, but Max finds himself drawn to the rival's son, complicating his loyalties.

Brad and Jane host a couples game night with their friends, which turns increasingly competitive. At the same time, Dave faces an important career decision, and Alex's attempts to assist lead them to an unexpected visit with a psychic.

Penny claims to be over her breakup with Pete, but her friends grow concerned when she writes a play titled "Black Plague: A Love Story" and enlists Derrick and his theater group to produce it. At the same time, Alex and Max are approached by a marketing firm to serve as taste makers.

Penny quickly moves on from her breakup with Pete by beginning an unexpected affair with the Car Czar, surprising her friends. She temporarily stays with Brad and Jane, who take on a parental role and disapprove of her choices. Meanwhile, the group urges Max to find employment to stop relying on them financially.

Max, after being mocked by his ex-roommate Chase for leading an unremarkable life, becomes determined to improve himself with Jane's help. At the same time, Alex turns to the group for assistance in using her large collection of Groupons, after being challenged by Dave.

Penny and Dave are thrown for a loop when their parents, Dana and Big Dave, announce their plan to adopt a baby, leading to their typical over-the-top reactions. At the same time, Brad and Jane attempt to join an elite tennis club, but their efforts are complicated by Max and Alex, who keep showing up.

Jane takes on the challenge of planning a wedding for her seemingly flawless older sister, Brooke, while Brad struggles to connect with Brooke's accomplished African American fiancé, Elliot. Meanwhile, Alex and Dave are keeping a significant secret.