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. She doesn't feel like she's really making a difference, until a friend shows up in need of a little mouth-to-mouth.
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.
In "The Slump", 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. When Jenna gets the job and threatens to fire Tucker, Ben must come to his buddy's rescue.
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. Amy 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.
Tucker reignites a relationship with an ex who has it out for Ben. Meanwhile, Danny attempts to set up Riley with his hot new teammate.
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. Meanwhile, Riley tries to get her old job back with Bonnie's help.
Ben convinces Bonnie and Ray to invite conservative Aunt Betty to Emma's baptism in the hopes she'll write a nice, fat check for Emma. The Wheelers nearly pull off their ruse as a perfectly normal family, until Ray's boyfriend Steve shows up demanding answers. Meanwhile, Ben enlists Riley to choose Emma's godfather, and she can't decide if Danny and Tucker are really up to the task.
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 finds out that his neighbor Kayla is hosting a playgroup for all of the kids in the neighborhood but is excluding Emma. Ben devises a plan to sneak Emma into the group but when Kayla busts him, he and Tucker start a rival group of their own. Meanwhile, Danny and Amy have some relationship trouble and Danny finds a permanent way to show Amy he is committed but ends up making a huge mistake.
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 and Danny shop at the last minute to buy Emma the perfect toy, which leads to them making a deal with Edwin, a shady mall elf. Riley and Tucker are appointed Bonnie's "little helpers", to help pull off the perfect Christmas for the apartment.