Ben and Riley try to transition from friendship to being a couple, which results in a hugely embarrassing moment for Riley. Ben is still angry with Bonnie for bringing Emma's mom Angela back into their lives. Angela tries to show Bonnie she's a capable mother while hoping for a fresh start with Ben. Meanwhile, Tucker tries to help Danny get over Riley and Amy with his five-step "T.U.C.K.E.R". break-up recovery system.
Angela has been crashing in the boys' apartment, trying to spend more time with Emma and get closer to Ben. Her presence puts strain on Ben and Riley's relationship, but Ben doesn't have the heart - or the guts - to ask her to leave. Tucker plots to show Riley that Angela is trying to steal her man and Danny decides that the only way he can heal his broken heart is to get his own apartment. Meanwhile, Bonnie begins dating a younger man.
Ben catches Riley in a compromising position with her ex-boyfriend Fitch, which leads to a massive blow-out between the two. Danny worries that the combination of his low stats and his Rangers jersey not selling in stores means his future with the team is in jeopardy. Tucker gets a job assisting Mary Hart on her new talk show, "The Mary Hart Show", and sets his sights on becoming a producer. Bonnie convinces Tucker to have Danny as a guest on the show to increase his popularity, but when Mary digs a little too deep into Danny's personal life, he has an emotional meltdown.
When Riley's firm is hired to represent the scandalized Reverend Stockdale, she is charged with making sure his daughter, Piper, stays out of trouble - a task that seems relatively easy given Piper's boring personality. But when Riley's away, Piper will play, and Danny and Tucker find themselves tangled up in her wild child ways. Meanwhile, Bonnie's real estate career is off to a sizzling start when Ben unknowingly burns down her first listing.
When Ben's rooftop beach gets shut down by the current apartment Board President, Sondra, the boys campaign to overthrow her and preside over the building themselves. The only problem is they have to decide who has the best chance to win the election, which won't easy given their spotty history with the other tenants. Meanwhile, Bonnie drags Riley on a double date with her boyfriend Brad and his twin Tad, but it doesn't take long until the ladies suspect that Brad has made Tad up in order to escape accusations of infidelity.
Tucker and Ben swap names to win over a woman; Riley uses Danny in an attempt to impress a friendly adversary; Bonnie's new business slogan creates the wrong effect.
Riley bets Ben that he can't get a second date with Heather. He gladly accepts the challenge, but when Heather doesn't jump at the chance to go out with him again, Ben resorts to desperate measures. Bonnie decides to break up with Brad, but when her realtor boyfriend declares his love, she can't bring herself to go through with it and asks Danny to end the relationship instead. Further complicating things as only Bonnie can, her love life takes another twist when she unknowingly falls for Brad's. Meanwhile, Tucker uses Emma to pick up women.
Tucker still hasn't told his dad that he's not a lawyer, which proves to be a problem when Marshall Dobbs unexpectedly arrives for a visit. Tucker and Ben devise a plan to keep the charade going, but it eventually backfires when Marshall learns the truth. Riley falls for a handsome Brit she meets at the bar and tells Bonnie that she finally found "the one"; however, Bonnie mistakenly believes that Riley is talking about Danny and immediately encourages him to go after his true love. Meanwhile, the group's trip to the renaissance faire hits a snag when a sword fight breaks out in the subway.
Ben is less than thrilled when Riley asks him to hang out with her new boyfriend, Philip, but he reluctantly agrees once Riley plays the friendship card. However, the man-date goes horribly wrong when Ben's harmless flirting with a student puts Philip's job at the college - and his visa - in jeopardy. Danny's hockey playing is criticized by a sports reporter, Logan, but that doesn't stop him from hitting on her, prompting a horrified Bonnie to embrace her inner enforcer and take matters into her own hands. Meanwhile, Tucker discovers the power of the British accent.
A horrified Ben realizes that he dated Tucker's new girlfriend, Stephanie, and is convinced she's only with Tucker to get back at Ben for their bad break-up. Riley is delighted when her boss, Ms. Jensen, finally asks her to participate in the firm's spa day, but her joy is short-lived when Bonnie is also included in the outing. Riley knows Bonnie will embarrass her and ruin her chances at making partner, so she tries to disinvite Bonnie and enlists Stephanie to be her plus one instead. But when the boys crash their spa day in a misguided attempt to save Tucker's relationship, it's a case of mistaken identity when the very intimidating masseuse puts them to work.
Bonnie sets Ben up with Bailey, a fast-talking, animated spitfire with plenty of attitude. Everything seems to be going well until Ben realizes his new girlfriend is a mini version of his mother and he has to break up with her. However, Bailey refuses to be dismissed so easily, and Ben resorts to desperate measures to get her out of his life once and for all.
Meanwhile, Danny pulls his dad's beloved car out of storage, but it's a bumpy start for "Adele the Chevelle" once Tucker and Riley get a hold of the keys.
Ben is determined to give Emma the perfect first birthday party, especially since his own was less than stellar. When he decides to host it at the ice cream parlor where he and Riley worked as teenagers, Ben runs into an ex-girlfriend with a mother of a secret. Danny accidentally discovers something about Riley's family that turns her world upside down. Meanwhile, Tucker is in charge of entertainment for the birthday party, a responsibility he takes very seriously.
A lovesick Bonnie realizes how much she misses her ex-boyfriend Brad and turns to Tucker for help reuniting with her true love. But when Brad confesses that he still has feelings for Bonnie, Ben's well-intentioned but misguided advice leads Brad to make a rash decision. Riley wants to have the relationship with Margot she never had with her adoptive mom, but first Riley must learn to appreciate Margot for who she is, flaws and all. Meanwhile, Danny must stop Riley from taking the next step with Philip.
Bonnie is tired of not being appreciated for everything she does for the boys and Emma and decides to go on strike. When it's quickly obvious they can't survive without her, Ben realizes the best way back into his mom's good graces is to take her to the Bon Jovi concert. But when Tucker unknowingly buys fake tickets, Bonnie must get through time in Bon Jovi jail, a tough security guard and a little dilemma in the green room if she hopes to meet her idol. Meanwhile, Riley and Danny return to their high school to chaperone prom and run into Vice Principal Peters, who's still inappropriately enamored with Danny.
Now that Riley knows the truth about Margot, she decides to find her biological father and uses her parents' high school yearbook as a guide. With a little help from Ben, Riley narrows down the possible candidates to David, the easygoing pastry chef, and Mark, the high-powered attorney. But despite some initial deception and old teenage rivalries resurfacing, Riley finally learns her father's identity. Meanwhile, Tucker is not happy about his parents' divorce and realizes the source of their problems is that Marshall is too uptight. But when Danny asks his mom to help Mr. Dobbs loosen up, Bonnie takes the challenge to a whole new level.
Riley is looking forward to meeting Philip's sister from England, but her excitement soon vanishes when it becomes obvious that Georgie is less than impressed by her brother's taste in girlfriends. When Ben makes a huge mistake and accidentally lets it slip that he and Riley once dated, she tries to convince Philip that he's the one she wants to be with. But will Philip's doubts about her feelings for Ben put an end to their relationship? Meanwhile, Danny's contract negotiations are in jeopardy when Bonnie tangles with the Rangers' new general manager, Valerie. Once Valerie sets her sights on Tucker, Bonnie believes she's found the perfect way to seal Danny's future with the team.
Ben, Danny, and Riley take stock of their lives when they review their fifth-grade time capsules.
Ben wants to see Emma walk and tries bribing her with food, but it doesn't work. Instead, she toddles after he leaves for work, so the gang devise a scheme for him not to miss out on this milestone. Meanwhile, everyone reflects on Emma's infancy.
Bonnie decides to baby-proof the apartment and sells the foosball table to struggling fraternity Sigma Beta Kappa, unaware that Ben had been hiding money in the table for Emma's college fund. Ben and Tucker pose as pledges in order to get the money back, but their fake identities cause more trouble than they're worth. Meanwhile, Riley is not happy that Danny is dating Georgie, especially because she blames the Brit for ending her relationship with Philip. But when Georgie secures Riley an interview for the in-house counsel job at Vogue, Riley begins to look at her rival in a new light - at least until she overhears Georgie admitting the interview was bogus. Riley can't wait to tell Danny the truth about his deceptive girlfriend, but can she really break her best friend's heart?
Riley plans to attend her family reunion in Orlando, but since she hates to fly, she decides to take the train instead. Ben realizes this trip is the perfect opportunity to rekindle their romance and volunteers to tag along. However, when Riley thinks he's only after one thing, Ben manages to convince her that his feelings are genuine. Can she bring herself to trust him with her heart once again? Meanwhile, Tucker has the chance to be Mary Hart's co-host and asks Bonnie for help with his audition tape. But when Mary decides to give Bonnie the job instead, Tucker is forced to play dirty in order to eliminate the competition.
Bonnie enlists the gang to crash a sports competition in her old neighborhood; Riley and Ben learn the truth about Danny's feeling for Riley; Danny considers moving to Paris with Georgie.