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.