While looking for a new bar manager, Ben interviews his old crush Sam, and decides to get revenge on her for never noticing him in high school. But things don’t turn out as planned.

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 Ben learns that Sam’s living arrangements have fallen through, he schemes to push Danny and Riley to move in together so Sam can take his room.

Riley is frustrated that Ben only has eyes for Sam and not for Zoey, who she thinks is perfect for him.

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 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.

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.