Dave's fling begins turning into a relationship he doesn't want; Jane tries to help Alex find a roommate.

Jane thinks she and Brad should befriend a sophisticated couple; Max and Dave notice that things are disappearing from their apartment; Alex starts dating an artist.

When Brad's dad receives good news on some medical tests, his new view on life is difficult for Brad to accept; Penny meets an attractive Italian, but she can only speak to him when she's drunk.

Brad plays matchmaker to a co-worker; Penny regrets inviting Jane to her martial-arts class; Dave helps Alex with odd jobs, leading his friends to think he wants to get back together with her.

Former couple Dave and Alex regret their couples tattoos; Jane feels Max is missing Mr. Right.

An old friend gets married, and the bride thinks Alex is a jinx; Penny and Derrick pretend to be engaged.

Alex and Jane's sibling rivalry heats up; Dave dates an attractive woman (Bre Blair) with an unusual quirk; Penny gets an assistant

Jane convinces Penny to make a vision board to visualize the path to her dreams, although everything doesn't go according to plan. Brad finds it hard to relate to his stern boss until the guy sees Max's limo. Dave is reluctant to let the gang to meet his new girlfriend.

Penny, Max, Dave and Alex head to a Halloween warehouse party, where their costumes don't have the effect they anticipated. Meanwhile, Jane and Brad spend their Halloween house sitting for some friends in the suburbs.

Dave has a surprising reaction when his shrink starts dating Penny. Max and Jane's fight over a sweater leads to a strange competition, and Alex and Brad bond when they discover a shared interest.

Things spiral out of control after Penny tells a white lie to avoid an irritating childhood friend. Dave and Max's lonely and jealous landlord falls for Alex.

The gang find themselves at yet another wedding, this time the nuptials of Derrick and Eric. Brad struggles to tell Jane something important, Jane tries to find a way to help Eric hide the fact that the pricey reception must be downscaled, and Max tries to find the courage to perform with his old all-male Madonna cover band. Meanwhile, a dateless Penny is sad that she's at another wedding, alone, until she meets cute guy Chris via Skype.

Dave and Alex start seeing each other again; Max tends to Penny after an accident lands her in a full body cast, but when he starts crushing on her physical therapist, he tries to impede her recovery; Brad tries to keep a secret from Jane.

Dave and Alex's inability to commit to a new apartment proves to be quite a challenge for their real-estate agent, while Jane pulls out all the stops when she takes Penny car shopping. Later, Max shows out-of-work Brad how easy it is to spend a cashless Saturday in Chicago.

Alex signs up the gang to participate in the Northside Kickball Classic tournament. However, self-appointed manager Max has difficulty bringing his players up to scratch - Dave has a history of freezing at crucial moments after an unfortunate incident during a previous game, Penny uses the tournament as an opportunity to meet good-looking guys and refuses to put on appropriate footwear, while Jane abandons her friends altogether and started playing for another team.

The gang is shocked when Penny rebounds from her breakup with Pete by having a torrid affair with the last man on earth they'd pick for her -- the Car Czar. To make matters worse, she's temporarily living with Brad and Jane, who end up acting like disapproving parents. Meanwhile the friends pressure Max to get a job so he'll stop sponging off them.

Chase, the ex-roommate whose life Max ruined, says he'd like to take revenge and do the same thing to Max, but Max's life is so pathetic it's "un-sabotagable." Max vows to prove him wrong and asks Jane to help him get his act together. Meanwhile, Alex asks the rest of the gang for help when Dave challenges her to finally use her stockpile of Groupons.

Penny's mom, Dana, and Dave's dad, Big Dave, are in town visiting, and these two lovebirds are not only going strong, they've decided to adopt a baby together, prompting Penny and Dave to react the only way they know how - irrationally. Meanwhile, Brad and Jane decide to try to join an exclusive tennis club, but unfortunately Max is on the scent and they can't shake him...or Alex.

The third Kerkovich sister, Brooke, is the alpha sister of the group, and Jane has the daunting task of planning a wedding for her more perfect and exquisite older sibling. Meanwhile, Brad is having a tough time himself dealing with Brooke's equally more perfect African American fiance, Elliot, and Alex and Dave have a big secret they're hiding.

When Max tries out Jane and Alex's long-time hairdresser, Krisjahn, he gets some good salon gossip on the girls, but his loose lips may cause World War III between the Kerkovitch sisters. Meanwhile, the Steak Me Home truck is stolen and Dave and Penny try to figure out whodunit.

When Ryan, Jane's ex, comes to town for a visit, Brad is surprised to learn that Ryan is a woman. Meanwhile Max gets a super cool new roommate, Chase, who immediately upgrades the apartment with expensive furniture and gadgets. The gang is in awe, but when Chase suddenly disappears, they start snooping into his private life.

With the wedding coming up, Penny decides to reach out to her estranged dad Roy. The reunion is sufficiently awkward but Alex encourages Penny to be optimistic, while Jane is more skeptical. Meanwhile, Dave enlists Brad and Max's help in sabotaging "The Brazilian" food truck, a.k.a. Dave's #1 nemesis, but Max accidentally falls for the enemy's son and has to choose between his best friend or boyfriend.

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.

Jane encourages Penny to find a man and then change him to suit her expectations. Alex stages an intervention to stop Dave from his obsession with V-neck shirts.

After years of bad luck every time the gang celebrates Penny's birthday, the gang starts to believe the day is cursed.