Riley faints after Danny asks her to marry him; and when she wakes up, she has no memory of his proposal. Trying to move on from Riley, Ben decides to find "his Riley" and immediately hits it off with new neighbor Zoey. However, Ben is shocked when their first date reveals he and Zoey have more in common than he thought. Bonnie is determined to finally marry Brad after many aborted attempts, and believing Ben and Danny are to blame, enlists Tucker to help her tie the knot without her sons' knowledge.
When Emma starts calling every woman she sees "Mommy", Ben decides it's time to find someone with whom to be serious. He turns to Riley to find him a date, but she thinks Ben is not ready to settle down and sets out to "build a better Ben". Meanwhile, Danny asks Bonnie for help when his sleeping troubles affect his hockey performance. But her help could get Danny into even bigger trouble with his team.
While looking for a new bar manager, Ben interviews his old crush Sam, and decides to exact "Ben-geance" on her for never noticing him in high school. However, once Ben sees Sam again, his plan to make her believe she got the job and then take it from her unravels. Bonnie decides marrying Brad means he's always going to be around causing her to reconsider their union. And Danny can't stomach Riley's cooking, but doesn't have the heart to tell her.
Thinking Tucker needs to stand up for himself with his boss Mary Hart, Ben films Mary berating Tucker to show how badly he's being treated. But when Emma accidentally uploads the video online, Mary and Tucker become a viral sensation, leaving Tucker in an even worse spot. And Riley asks Danny to stand up to Bonnie and tell her she can't always hang out with them, but Bonnie has a trick up her sleeve to outwit Riley.
Tucker finds Zoey snooping around his apartment and assumes she is there for him, so he takes it upon himself to ask her out. However, Zoey believes Tucker is setting her up with Ben. Danny finds himself in a similar situation when he tries subtly asking Sam how he feels about Ben, but she thinks Danny is asking her out. And Riley finds herself in an uncomfortable situation when her client tries to take things to the next level with Bonnie. Are there any perfect matches?.
When Danny finds out that Ben is still Riley's emergency contact, he acts as if Ben and Riley's relationship didn't count. So, when Ben attempts to prove that his and Riley's relationship meant something, things become awkward for Riley and Danny. Meanwhile, Bonnie flirts with someone who's in power to further her own agenda, and Tucker rekindles an old flame.
Now starring on a hit television series, Emma's mom, Angela, unexpectedly returns and wants to see Emma. Ben is reluctant to comply, but when Angela claims she can help get Emma into a good preschool, Ben relents and asks Riley to keep an eye on them. Bonnie is temporarily managing the bar and takes the opportunity to try out some new ideas. And Tucker is living in fear, since he's convinced that Mary Hart is now out to get him.
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, which involves Danny vacating his room. However, Ben's master plan doesn't work out too well when Sam brings home her boyfriend. And when Bonnie recruits Tucker as an assistant for her new job, she finds herself actually working for Tucker.
Riley is determined to set Ben up with Zoey, believing they would be perfect together. But both resist her attempts, insisting they don't have feelings for each other. Meanwhile, Tucker auditions to be a local weatherman, but Bonnie inadvertently ruins his chances when she tries to get Danny a job as a sportscaster.
Sam invites Ben, Riley and Danny to the Hamptons for the weekend, leaving Ben confused as to whether he wants to be with Sam or Zoey. Riley finds some old home movies of everyone in high school, but she discovers more than a trip down memory lane. Meanwhile, Bonnie is convinced that Brad has moved on, so she also moves on with another guy, however their evening does not turn out as planned. And Tucker is excited to finally have the apartment to himself.
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 decides to try and set a good example for Emma by returning to high school and get his diploma.
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.