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.
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.
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.
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.
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.
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.
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\".
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.
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.
Dave has an odd reaction when his shrink starts dating Penny. Meanwhile, Jane and Max fight over ownership of a sweater and end up in another one of their strange competitions; whoever is "less vain" gets to keep the sweater, and the challenge is to see who can wear a horribly unflattering outfit the longest.
Dave's father, "Big" Dave, comes to town to introduce his new girlfriend, who shockingly happens to be Penny's mother, Dana. Penny couldn't be more thrilled that her thrice divorced mother has a new man in her life, but Dave on the other hand reacts childishly to the news.
Jane convinces Penny to stop changing herself for every guy she dates, and instead to change the guy to suit her needs. Penny\'s first experiment is Jeff, a slacker who is 30 going on 20.
The road to romance is rocky for the gang, as Penny has a new boyfriend she wants to dump; Dave is afraid his new girlfriend is about to dump him; Alex, an expert on all things Valentine's, goes looking for a party in the sketchy part of town; and Brad's hopes for a perfect night out for Jane are dashed when a dental appointment goes terribly wrong.
When the whole gang, with the exception of Dave, falls in love with Grant, Max wonders if he really is good enough to date the \"perfect\" guy. Meanwhile, Dave sets out to prove he\'s way cooler than Max\'s new boyfriend.
Some people wait for the groundhog to signal the end of winter. Instead, the friends wait for Brad and Jane\'s annual \"spring smackdown\", their yearly blowout of a domestic squabble, to let them know when Max will come out of hibernation and when winter will end.
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.
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.
So many bad things have happened every time the friends celebrate Penny\'s birthday, they\'re wondering if her special day might be cursed. They set out to find a restaurant where they can celebrate, where one of them hasn\'t been banned or where someone won\'t run into an ex - something that\'s almost impossible.
Dave finds himself bullied at the gym by Corey, and former bully Alex coaches him on how to fight back. Meanwhile, the residents at Brad and Jane\'s condo are fed up with Jane being too controlling as president of their home owners\' association, and rise up to challenge her for the job. But when Penny tells Jane to \"sleep on it\" before she does anything rash, her advice results in an all-new, suddenly chill Jane.
What starts out a white lie on Penny\'s part to avoid an annoying childhood friend snowballs out of control as the whole gang is caught up: Jane fakes a pregnancy, Dave pretends he\'s terminally ill and Alex fakes a change in sexual orientation. Meanwhile, Max and Dave\'s lonely landlord, jealous of their active love lives, looks for ways to evict them - until he takes a shine to Alex.
The gang find themselves at yet another wedding, this time the nuptials of Derrick and Eric. Will there be "DRAMA," to quote Derrick? Of course, as 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.