Bobby is Jackson's best friend, or as he likes to put it, his 'Kimmy Gibbler'. Bobby likes to live life on the extreme side, urging his friends to do dangerous and extreme activities including skateboarding off roofs and wrestling while he records and ultimately uploads the videos to YouTube. According to Max, Bobby's parents are very rarely at home, leaving Bobby by himself most of the time.
Bobby, Jackson and Ramona text each other while sitting in the same room together. After Jackson leaves Bobby suggests Ramona get her first kiss out of the way with someone she doesn't even like. Ramona and Bobby kiss twice, the second time Max and Cosmo walk in on them.
Bobby texts Jackson to see if he and Ramona would like to join him and some friends to the movies. When he arrives Ramona finds out he already has a girlfriend, Bethany.
Bobby tells Jackson he dumped Bethany because she didn't blink enough, and now wants to go out with Ramona. When he asks Ramona to hit the mall and share a Cinnabon she says no and embarrasses him in front of his friends.
Bobby uploads a video of "Ramona Gibbler - The Dancing Hippo". When Jackson finds out he uploads a video of Bobby skateboarding and farting called "Bobby POOP-ko", Bobby blames Ramona for posting it. Jackson admits it was him and Bobby apologises for the video he posted of Ramona.
Bobby, Jackson, Ramona and Lola get together for a New Years eve party and Max wants to celebrate with them. Ramona makes no promises to kiss Bobby at midnight. Jackson and and his friends trick Max with the Netflix fake countdown to midnight, and send him to bed in Tommy's room.
Bobby and Jackson apply cologne in Jackson's room to get ready for midnight. Max and Rose work to get revenge on Jackson, Ramona, Lola, and Bobby by tying a rope to the door knobs of both Jackson and Ramona's rooms. Locking Jackson and Bobby in one room and Ramona and Lola in the other. D.J. realises what is going on and lets everyone out.
Bobby and Ramona give each other a high five to ring in the New Year. When Bobby tells Ramona he didn't need a kiss from her, Ramona gives him a big kiss.
Bobby apologises to Ramona for giving her a hickey and that he couldn't help it. Ramona and Bobby attend Laser Tag together. When Kimmy arrives Bobby's zit cream is illuminated under the lights, and so is Ramona's make up covering her hickey. When Kimmy finds out Bobby gave Ramona a hickey she glares at him.
Bobby gives Ramona a card with a poem inside saying he wants to see other girls while she is in Japan for the following 5 days. Ramona responds by dumping him.
Not only is Sienna wearing the same dress as Ramona but her prom date is Ramona's ex-boyfriend Bobby Popko. Sienna commands Bobby to stand up straight. When Sienna ditches Bobby, he goes looking for Ramona. He only came with Sienna because the girl he wanted to go with hates him. Bobby apologises for messing up their relationship, he can't believe he let go of someone so amazing. Bobby misses Ramona and hopes they can be friends. He and Ramona dance together.
With only two hours until the wedding, Rocki Mahan and Ethan help Jackson and Ramona set up. When she received Ramona's invitation to a triple wedding, Lola thought you can miss one wedding but not three. Jackson stairs at Lola. Ramona introduces Lola to Ethan. Rocki introduces herself to Lola. Ethan escorts Lola to where the guests will be sitting. Rocki is upset with Jackson for not introducing her to Lola as his girlfriend. Ramona chews out Jackson for knowing nothing about relationships, then Bobby arrives. He already knows Ethan, as his Postmates guy. When Bobby inquires as to how Ramona knows Ethan, she can't tell Bobby that Ethan is her boyfriend.
He sits towards the back, next to Vicki Larson and Lola. Everyone stands as the wedding ceremony begins. Jackson, Ramona, Max, and Tommy wait along side Fernando, Steve, and Jimmy for the brides-to-be. First Joey walks Kimmy, then Jesse walks Stephanie, and last Danny walks D.J. down the aisle. Danny kisses his daughters before sitting with Joey Jesse, and Pamela. Jesse asks Danny for his name to go on his gift. Danny's gift was paying for the wedding. Joey inquires as to if Danny found a minister. Girls are thrilled to discover Joey McIntyre will be officiating their wedding. Joey McIntyre announces he is there to marry three New Kids superfans to their grooms. The couples wrote their own vows. Kimmy and Fernando go first, followed by Stephanie and Jimmy, and last D.J. and Steve. Joey McIntyre cries over the vows, he thought Please Don't Go Girl was romantic. D.J. Stephanie, and Kimmy say "I do" as they place rings on their respective grooms fingers. Fernando, Steve, and Jimmy say "I do" as they place rings on their respective brides fingers. Joey McIntyre pronounces the couples "husbands and wives". All guests stand up, clap, and cheer the newlyweds. Lisa Loeb plays guitar and sings First Day of my Life. The newlyweds share the first dance together as guests watch. Joey gives the first toast. Jesse gives the next toast. D.J. Stephanie, and Kimmy throw their bouquets. Ramona, Lola, and CJ catch them. Danny gives his toast.
- Often seen wearing a hat