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Nachdem die beiden Geschwister ihre Eltern verloren, trennten sich die Lebenswege des etwas verplanten Ben und der zielstrebigen Kate. Jetzt, Jahre später, besucht Ben seine Schwester immer wieder und genießt die Ordnung ihrer Wohnung als Ruhepol in seinem chaotischen Leben. Diesmal ist er in der Stadt, um die letzte Chance bei seiner Jugendliebe zu nutzen – denn die steht kurz davor, einen Anderen zu heiraten …

Kate benutzt eine Notlüge und macht falsche Angaben über ihren Wohnort, um Maddie in eine bessere Schule zu bekommen. Doch auch Notlügen haben kurze Beine …

Ben und Kate entdecken einen verschlossenen Briefumschlag ihres verstorbenen Vaters. Darin befinden sich Anweisungen für eine Schnitzeljagd. Sofort lassen sie die alte Familientradition wieder aufleben. Wie üblich ist Kate zunächst deutlich motivierter, doch dann merkt Ben, dass der Preis wertvoller ist als gedacht …

Bens Jugendliebe Darcy zieht mit ihrem Ehemann in das Haus, das Ben für seine Zukunftsvision mit ihr vorgesehen hatte. Jetzt will er zumindest den Baum vor diesem Haus stehlen, denn auch für ihn hatte er konkrete Pläne: Ben wollte daraus ein Kanu bauen, um Darcy nach ihrem Tod nach Vikinger-Tradition zu bestatten! Auch sonst hat Ben einiges vor. An Kates Wunsch, den eigenen Geburtstag nicht zu feiern, will er sich nicht halten …

Kates Überfürsorglichkeit in Bezug auf Maddie macht Ben wahnsinnig. Jedes Wehwehchen der Tochter ist für Kate ein medizinischer Notfall, auf den außer ihr natürlich niemand richtig reagieren kann – schon gar nicht Ben, zumal der in Kates Augen viel zu sehr vom Auftauchen der hübschen Louise abgelenkt ist. Gemeinsam mit Tommy und Louise entwickelt Ben einen Plan, um Kate klarzumachen, dass selbst sie nicht für alle möglichen Vorfälle gerüstet sein kann …

Kate gets invited to her hot neighbor's Halloween party, so BJ tries to help Kate break free and be someone completely out-of-character for the night. Meanwhile, Ben and Tommy decide to stay home and hand out candy to the trick-or-treaters in hopes that they'll meet some hot moms, but the night takes a turn when Tommy unknowingly eats some of BJ's "candy" from Amsterdam, and Kate bonds with Will (guest star Stults), a single father.

With Career Day at Maddie's school coming up, Ben wants to find an actual job so he can make his niece proud. Meanwhile, Kate starts to develop a crush on her neighbor Will, and BJ face backlash from a co-worker at the bar for getting a raise.

When a high school reunion is held on the eve of Thanksgiving, Will (guest star Geoff Stults) encourages Kate to attend and stand up to the high school bully, Anna (guest star Amber Stevens) for giving her an unforgettable nickname. Meanwhile, in the midst of the holiday season, Ben doesn't think he can keep much longer the huge secret that he and BJ have been hiding from Kate.

When Kate sees the face that Will makes while playing guitar during his cover band's performance, she gets turned off and unable to take him seriously. Meanwhile, Tommy gets Ben a job at the country club which soon backfires for both of them, and BJ attends a support group where she gets good advice about her friendship with Kate.

Although Ben, BJ and Tommy disapprove, Kate and Will take their relationship to the next level when they go on a romantic camping trip together. Of course, the trip quickly goes awry when some unwelcome guests decide to tag along. Meanwhile, BJ makes it her mission to help Tommy move past his feelings for Kate.

When Maddie fails the test to get into the gifted program at her school, she becomes part of "The B-Squad." Kate, who blames herself for Maddie's failure, decides to take matters into her own hand and gives The B-Squad an unforgettable experience. Meanwhile, Ben runs into an old pal from college who stole one of his business ideas, and BJ's mother, Wendy, comes to town and gets a surprising introduction to Buddy.

Tommy finally brings around his new girlfriend, Lila, to meet the gang. But when Kate suggests the two women get to know each other, things don't go as planned. Meanwhile, Ben moves forward with his "Rail Mall" business plan.

Ben continues to expand his "Rail Mall" idea with his new business partner, Vera, but when she brings in more associates to help expand their plan, Ben doesn't like the direction in which it’s heading. Meanwhile, after finding out that Will has been dating since their break-up, Kate goes on a date with a baker she met at Will’s party. Also, BJ and Maddie pose as mother and daughter for a commercial audition.

When Ben and Kate's father, Randy, pays an unexpected visit, chaos ensues. Kate starts asking big questions about herself and her life trajectory, causing a big fight between her and BJ. Meanwhile, Ben confronts his dad about all the things they never did together, as they search, with Tommy, to finally find and accost Maddie's dad for running out on Kate.

The siblings' dad Randy closes a business deal with Kate's help, leaving Ben feeling sidelined. Ben tries to upstage Kate by volunteering to organize the annual father-daughter dance at Maddie's school.