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Chase wants to destroy Max for ruining his life but declares Max's life as " un-sabotagable ". To prove him wrong, Max goes to Jane to help him get his act together. Dave urges Alex to use up all her Groupons, so she asks the gang for help.
Jane has the off-putting job of planning older sister Brooke's wedding. Perfect Brooke is the alpha sister of the group and Brad is having a tough time dealing with her equally more perfect African American fiance. Dave and Alex are hiding a big secret.
As Penny deals with her breakup with Pete, she writes a play titled " Black Plague: A Love Story" and asks Derrick's theater group to participate. Alex and Max are asked to be tastemakers.
Jane and Brad decide to have a couples game night but things get cutthroat which in turn triggers an unexpected move by Penny. When Alex tries to help Dave with a big decision they end up at a psychic.
Dave and Alex can't seem to agree on an apartment. When Penny needs a car, Jane negotiates for her. Max introduces Brad to the techniques for having a night out free.
Alex and Dave are dating again. Penny's accident leaves her in a full body cast, but when Max falls for her physical therapist, he tries to slow down her recovery. Brad hides a secret about his unemployed status from Jane.
Max pretends to be straight when he meets a cute girl with season tickets for the Bulls. Tired of being the dumb blonde, Alex decides to become well read which in turn throws off the group's dynamics.
Penny seeks out her estranged dad Roy to be at her wedding. With help from Brad and Max, Dave sets out to sabotage his food truck nemesis but Max find himself in a dilemma when he falls for the enemy's son.
Who needs a groundhog! Brad and Jane's yearly argument gone wild lets the gang know that the end of winter is near.
Dave's not as captivated with Max's new boyfriend like everyone else, so he sets out to prove he's more awesome than Grant.
Brad applies his business skills to keep Chuckles and Huggs open. While Penny and Max try to break their texting habits, they turn to Noche Tussin so they'll sleep instead of texting.
Max has been working as a professional "hype guy" at Bar Mitzvahs but, when he teams up with Brad to form a "hype guy" duo, jealousy and tension take hold. Jane pushes Alex and Dave not to take each other for granted this time around.
The gang starts thinking about the coming "zombie apocalypse" after watching a horror movie, so Max and Jane compete to see who would survive if zombies did take over. For his response, Dave decides to quit his boring job and open a restaurant. Trying to keep up with her current hipster boyfriend and his friends leaves Penny exhausted.moreless
As far as romance, nothing goes as intended for the gang on Valentine's Day.
Jane's big secret is out - she was born on December 25. She's been lying about her birthday because she didn't want it to be overshadowed by the holiday. Everyone decides to quit Christmas and throw Jane a Christmas-free birthday celebration.
Penny starts dating Dave's shrink. Jane and Max's fight over who owns a sweater leads to another strange competition, this one involving vanity and ugly outfits. Jane wants Brad and Alex to bond which is tricky, until they discover their shared love of romantic comedies.
Dave's new liquor license brings in lots of new business to the "Steak Me Home Tonight" truck but his friends are avoiding him. He thinks they're jealous of his success but it's really all about the effects of his new signature drink.
Max is out for revenge when the big lotto jackpot he thought he won turns out to a prank. Pete proposes to Penny. Jane is not amused by Brad's new job.
Alex designs a dress for Jane to wear to her charity event while Penny helps out Max with babysitting duties. Dave and Brad decide to strike up a friendship with their odd mailman.
Jane persuades Penny to change her dates to how she wants them to be rather than the other way around. But when Brad hears Jane boasting to Penny how she made over Brad after they met, he rebels. Alex and Max are convinced an in-T-vention is needed to break Dave's obsession with v-necked T-shirts.moreless
The gang spends Thanksgiving dinner at Alex and Dave's new place where Dave is determined to share a real Navajo Thanksgiving. When Max pulls up a copy of the lost season of "The Real World", everyone starts reminiscing about how they all met ten years ago.
Would-be wedding coordinator Jane tries to talk Pete and Penny out of eloping by taking the gang to a wedding expo. At the expo, Max and Brad end up in the gay wedding part while Alex and Dave are forced to deal with their own wedding issues.
Max's high school girlfriend, Angie, is back in town and each of the gang has a different reaction after meeting her. But Max declares a "code war" when Dave starts dating Angie. Jane decides to get a "work husband" after she discovers that Brad has a "work wife".
Penny's birthday celebrations are always disastrous for everyone. This year the gang is determined to find a restaurant that will break the curse so Penny can enjoy her special day.
Penny's got a new guy but the helmet she has to wear because of her concussion may put an end to the romance. Jane tenaciously pursues being part of the "boy's club" at the car dealership. Painful childhood memories flare after Max and Dave fist bump.
Alex teams up with Jane to convince Dave that something he's certain happened never did. Penny and Max are determined to finally beat Julie and Justin in the annual Rosalita's Run and Scavenger Hunt.
Penny's white lie to an annoying childhood friend rapidly grows out of control with the whole gang getting caught up in the lie. Max and Dave's landlord wants to evict them but that's before he falls hard for Alex.
Jane urges Alex and Dave to come clean with each other since it's the first anniversary of their almost-marriage. Penny buys an "amah-zing" condo which she feels will turn her life around.
Former bully Alex teaches Dave how to fight back against the bully at the gym. Jane's controlling ways as president of the condo association have the other residents fed up and challenging her for the job. But Penny's advise to Jane produces unexpected results.
Jane labors to come up with a joke that will make her dad laugh when she toasts her parents at their party for the 20th anniversary of the family mattress business. Dave finds out that Alex hasn't told her parents they're back together. Since Penny is occupied with a new boyfriend, Max goes looking for a new BFF.moreless
Big Dave comes for a visit to show off his new girlfriend, who it turns out is Penny's mother. Penny's thrilled but Dave reacts differently. Alex adopts a parrot whose nonstop verbal rhetoric is not so charming. Brad and Max are enlisted by Alex who thinks the Chinese restaurant next door is really a house of prostitution.moreless
It's another wedding for the gang. Derrick and Eric are getting married but the big question looming is whether there will be, as Derrick likes to say, "DRAMA". Brad has something important to tell Jane but she's busy helping Eric with reception details. Max tries to work up the nerve to perform with his old band. And Penny is again all alone at a wedding until she meets a guy via Skype.moreless
While Alex is away at her Rom-Com Com, Brad and Penny accidentally break her favorite childhood memento. While attempting to glue it back together, Alex's racist parrot dies from the glue fumes. Jane and Dave go overboard trying to find a match for Max.
Max gets some gossip on Jane and Alex after he uses their long-time hairdresser, but his big mouth may create a war between the sisters. Dave and Penny set out to find who stole the Steak Me Home truck.
Brad meets Jane's ex, Ryan, and discovers she's a woman. Max's new roommate, Chase, outfits the apartment with expensive furniture and gadgets and then suddenly disappears which starts the gang snooping to find out who Chase really is.
Alex and Penny see a way to use the press when a pop star buys a dress from Alex's shop. While Max has an identity crisis, Dave and Brad attempt to fix some things around the house.
Teen girls have made Alex's store their new hangout all because of Alex's "Put Me to Bed" t-shirts for babies. Jane goes into search mode when she thinks that an egg she donated back in college may have resulted in a now 11-year old girl.
Brad plans to skip out for a "staycation" when Jane's old sorority sister comes for a visit. Alex hooks up with new guy, but his dates are over-the -top. Max and Dave shoot a commercial for the "Steak Me Home Tonight" truck.
Penny's charity event has Max playing Santa. When Jane accidentally gives the housekeeper the wrong envelope of money – the one Brad filled with cash for their holiday getaway to the islands – she must come up with a way to get it back.
Penny's mom who's always enthusiastic and confident about the future is in town. The gang finds her high spirits contagious but Penny finds out things aren't as rosy as mom is making them out to be.
Alex is sponsoring a team for the city Kickball Tournament and convinces everyone but Jane to be on her team. They might have a shot at winning except that Dave freezes when it's his turn.
Jane decides everyone should make a vision board so they can all achieve their dreams. Brad finds it hard to relate to his stern boss until the guy sees Max's limo. Dave is hesitant for the gang to meet his new girlfriend.
Penny and Dave react absurdly when they find out that lovebirds Dana and Big Dave want to adopt a baby together. Wanting time for just themselves, Brad and Jane join an exclusive tennis club.
The gang heads to a Halloween costume party while Jane and Brad head to the suburbs after agreeing to house sit for friends.
Penny moves in temporarily with Brad and Jane and starts a rebound romance with the Car Czar. When the gang pressures Max to get a job and stop sponging off them, he enters the "Mr. Gay Guy Chicago" show.