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 was Ramona's first kiss.
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.