Ben begins to develop romantic feelings for Riley, but his reputation for being an irresponsible playboy works against him. Elsewhere, Tucker attempts to date a model and Bonnie uses Emma to get close to an attractive stranger.

Ben discovers a shocking secret about Riley's new beau, Fitch, and tries to warn her. Meanwhile, Bonnie accidentally sends a revealing message from Danny to Riley's cell phone. Things heat up between Danny and his new model girlfriend, Milena, and Tucker pounces on an opportunity to shine with his boss, Chase.

Ben discovers an endorsement opportunity for Danny with a new brand of Japanese energy drinks. Against Bonnie's advice, Ben convinces Danny to sign the deal, but he must pick up the pieces when things go haywire at Danny's commercial shoot. Meanwhile, Riley takes an interest in volunteering and accepts a job as a candy striper at the hospital.

Bonnie sets up her new bachelorette pad across the hall, and Ben and Tucker will do whatever it takes to force her out. They throw a huge party that threatens to damage more than Bonnie's new apartment. Meanwhile, Danny seeks Riley's advice on how to break up with Milena. Instead he ends up in a compromising position, which Milena mistakes for a marriage proposal.

Dr. Shaw determines Riley is the cause of Danny's inability to focus on the ice and bans her from Danny's next game. Meanwhile, Riley thinks things are moving too fast with Fitch and starts avoiding him, and gets her hopes up that Danny will make a move. Tucker is up for a promotion at work and his competition turns out to be Ben's latest fling, Jenna.

Ben tries to get Emma into daycare by flirting with the cute assistant manager, Megan. Megan insists there is no space, until she gets the idea that Ben and Tucker are a gay couple. Ben devises an elaborate plan to "break up" with Tucker in order to have a shot at dating Megan. Meanwhile, Riley worries that Dr. Shaw is trying to change Danny when Danny bails on their traditional "Halfaween" costume party.

Ben, Danny and Tucker band together to rescue Emma's missing stuffed animal. Meanwhile, Riley hosts a book club in an effort to make friends with the cool girls at work. When her mom, Jennifer, and Bonnie get wind of her plans, they invite themselves. Much to Riley's dismay, the ladies' long-standing rivalry erupts during the club meeting.

Riley plans to break up with Fitch, but then receives the news that Fitch is dead. She meets Fitch's dad, Winston Douglas, who asks her to deliver the eulogy at the funeral and tells Riley that Fitch planned to propose to her. Meanwhile, Ben realizes he might be in love with Megan, but she thinks things are moving way too fast. Tucker embarks on his "Tucket" list of things to do before he dies, and Bonnie schemes to catch the eye of Fitch's wealthy dad.

Danny plays matchmaker for Riley and his new teammate, who secretly likes Bonnie. Elsewhere, Tucker gets back together with an ex-girlfriend who doesn’t get along with Ben, and she winds up making Ben’s work life miserable.

Riley questions her future after taking the bar exam. Meanwhile, Amy takes a pregnancy test, while Danny tries to win over Amy’s father, who clearly dislikes him.

Megan’s dog is stolen while under Ben’s care. Riley tries to get her old job back with Bonnie’s help.

Ben suspects that Riley finds him attractive, as she asks him to help her find a man to date. Elsewhere, Bonnie and Tucker enter a mascot contest for the New York Rangers, despite Danny’s objections.

Ben resorts to devious measures to get Emma into the neighborhood playgroup, and Danny turns to Riley for help with his and Amy's relationship problems.

Ben learns why Riley doesn’t like celebrating her birthday and it’s all his fault. He knows he needs to make it up to her and plans a perfect birthday surprise, but in typical Wheeler fashion, disaster ensues. Bonnie realizes she may have made a mistake in filing Emma’s parental rights paperwork and Ben doesn’t officially have sole custody. Bonnie enlists Tucker’s help in tracking down Emma’s mother, Angela, to re-sign the papers. Meanwhile, Amy calls Danny on his lingering feelings for Riley.

Ben's quest to procure Emma the hottest toy of the Christmas season creates ill will; Tucker and Riley help Bonnie with holiday decorating.