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 …
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 tells Ben that she may quit her job as bar manager because of her long commute, he comes up with a solution to keep her close to work. When Bonnie recruits Tucker as an assistant for her new job, she finds herself actually working for Tucker.
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.
Danny is desperate to make up with Riley after their recent breakup, but she is still furious after learning he hooked up with Sam in high school. Determined to prove that she is not overreacting, Riley puts Danny on “trial” for breaking her heart, with Bonnie acting as Danny’s lawyer. And Ben tries to save face with Zoey after discovering that her ex has returned to get back together with her.
Ben discovers Tucker has been making extra cash by visiting a sperm bank. In order 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. Riley and Danny continue to fight while attempting to host their friend’s engagement party. Their moms, archenemies Bonnie and Jennifer, team up to get Riley and Danny back together.
Ben admits he never graduated high school and decides to go back to school in order to set a good example for Emma. Bonnie later confesses that she also did not graduate, so both must pass a final exam, instructed by Ms. Gilcrest, in order to get their diplomas. Riley and Sam are both inducted into the athletic hall of fame and argue over prime territory for their trophy case.
Bonnie is less than thrilled when she finds out that Ben invited her estranged mother Nana Lyle to town for Emma’s preschool’s family weekend. Meanwhile, Riley and Tucker enroll in an improv class in order to step out of their comfort zones and help them out in their respective careers.
Ben poses as Bonnie’s husband, Brad, when her friends from work don’t believe that she has an attractive, younger lover. When Danny begins dating a beautiful actress as a publicity stunt, Riley, who believes the relationship is real, decides to go back out with Ross to make Danny jealous. Tucker tries to further his entertainment reporting career by getting the real scoop on Danny and his new girlfriend.
As Ben and Riley both realize they are in for more than they bargained for with dating older, more mature adults, they work together 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.
When Ben receives an anonymous note from a past love interest asking for a second chance, he 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. Tucker, Riley and Bonnie enter Emma into a baby beauty pageant to get footage for Tucker’s news segment, but Riley goes too far.
When Ben’s first date with his new lover doesn’t go well, Danny and Riley step in to help sort out the couple’s issues, but their assistance quickly causes more harm than good. Tucker decides to tell his dad about his new relationship with Renee, one of his dad’s co-workers, but panics when he learns that his dad may have feelings for Renee too.
After Emma accidentally pokes holes in Ben’s stash of condoms, Ben, Tucker and Danny all fear their girlfriends might be pregnant. They discreetly try to find out if there’s anything to worry about while the girls pretend to have pregnancy symptoms to get them to confess the truth.
Ben forgets Emma’s birthday and attempts to combine her birthday party with a beer stand at the neighborhood street fair, but doing both at the same time proves rather difficult. Danny and Riley come to a crossroads when they are both offered new career opportunities. Bonnie and Brad must decide how to move forward once Brad returns home from his spiritual quest with a new outlook on life. Tucker cannot seem to get anyone’s attention as he processes through some exciting news of his own.