Riley faints after Danny asks her to marry him, and when she wakes up, has no memory of his proposal. Trying to move on from Riley, Ben immediately hits it off with new neighbor Zoey.
Ben wants to get back into the dating scene but Riley decides she needs to "fix" him first so he will be a better boyfriend. Bonnie gets Danny high but has to think fast when the hockey team drug tests.
Ben seeks"Ben-Geance" on the girl who spurned him in high school, Bonnie decides marrying Brad might not have been a good idea and Danny can't stomach Riley's cooking, but doesn't have the heart to tell her.
A video of Mary Hart berating Tucker goes viral after Emma accidentally uploads it online. Bonnie is left alone after Brad leaves to volunteer overseas and tries to spend all her time with Danny, much to Riley's chagrin.
Ben begs Danny to find out if Sam is interested in dating him but she thinks Danny is asking for himself. Zoey would like Tucker to help her with Ben but he misunderstands. Riley accidentally sets up Bonnie with a lesbian client.
Ben wants to prove that Danny is jealous of Riley's continued friendship with him, so he is willing to put himself in awkward situations involving Riley to get Danny jealous. Tucker continues to have casual sexual flings with Sondra, but ends up finally calling things off for good, having reached his patience with her annoying high-pitched voice. Riley is tasked with giving a heartfelt speech to Bernard Bender, one of the elderly founding members of her law firm who is retiring. Bonnie plans to use the opportunity to get close to Mr. Bender to elevate her real estate business.
Emma's mother returns and wants to see Emma, but Ben is hesitant and Tucker lives in fear since he thinks Mary Hart is out to get him, and Bonnie is temporarily managing the bar and takes the opportunity to try out some new ideas.
When Sam considers quitting her job at the bar because of a long commute Ben has the perfect solution. But mostly perfect for Ben. Bonnie starts a new job and hires Tucker as her assistant but things go terribly wrong.
Riley pulls some tricks to get Ben and Zoey together. Tucker tries to get a new job in the television business but Bonnie gets in his way. Danny wants to be a sports commentator.
After Ben and Zoey innocently spend the night together Sam shows an interest in Ben. She invites him, Riley, and Danny to the beach where a secret is revealed. Bonnie mishears a Skype message and thinks Brad is leaving her.
Riley is still heartbroken about finding out that Danny and Sam slept with each other back in high school and in puts Danny in a mock trial over her broken heart. Ben blackmails Zoey into pretending to date him.
Ben discovers Tucker has been making extra cash by visiting a sperm bank. To help Tucker pick up a nurse at the bank, Ben agrees to donate his own sperm but quickly regrets his decision after a couple chooses his sample. Meanwhile, Riley and Danny fight while attempting to host their friend's engagement party.
Ben confesses he didn't graduate from high school and it seems Bonnie didn't either. They need to take a make up test where Bonnie cheats and Ben is attracted to the teacher. Riley and Sam bond over getting into their school's hall of fame.
When Ben invites Bonnie's estranged mother to family day at Emma's school, tensions run high and old wounds are opened. Riley and Tucker take an improv class.
Ben pretends to be his mom's husband Brad when Bonnie's co-workers doubt his existence. Danny turns a fake relationship into reality with star Elena to make Riley jealous when she starts dating Ross again.
Ben and Riley realize they are in for more than they bargained for with dating older, more mature adults, and work to come up with a plan to get out of their respective relationships. When Bonnie and Tucker gain insider information about players on Danny's hockey team, they bet against the Rangers to win some cash.
Ben receives an anonymous note from a past love interest asking for a second chance, and does whatever he can to find the mystery girl. Danny misunderstands a note he thought was left for him and tries to get Riley back. Meanwhile, Tucker, Riley, and Bonnie enter Emma into a baby beauty pageant to get footage for Tucker's news segment.
Ben and Sam are finally a couple, and decide to have their first date. However, misunderstandings on what they want on the date, lead to Danny and Riley getting involved in their relationship, making matters worse. Tucker is dating his dad's secretary Rene (Chelsea Harris). After getting suspicious assumptions from Bonnie, Tucker begins to believe that his dad is also dating Rene.
Emma pokes holes in Ben's condoms using Bonnie's lost earring. Danny and Tucker have also been using Ben's condoms causing a pregnancy scare among the guys fearing that their respective significant others Riley, Rene and Sam are pregnant. Riley has difficulty dealing with an incompetent new assistant and asks for Bonnie's advice on firing him.
Ben tries to make things right with Emma; Danny and Riley are offered new career opportunities; Brad returns home; Tucker has exciting news but no one to share with.
