Name: Dean (last name unknown)
Age: 3 or 4
Voiced By: Pamela Segall Adlon
Dean is an older boy, who's mother is an acquaintance of Didi Pickles, whom she leaves him with to play with Tommy and the babies. He rides a kid's bicycle around the neighborhood. Angelica once fell for him, as he was "a 3-year-old's dream on a 4-year-old's bike". Dean is very friendly, dressing almost like a biker boy or similar to Elvis does with his hair. Dean seems to be oblvious to Angelica's cruelty to the other babies, it could be said that with Dean around it was the first time Angelica stopped trying to bullying the babies and tried to be nice. However once he was gone, she went back to being mean. Dean makes his first appearance in "Angelica In Love", as he becomes her first crush. Although for the most part, Dean was oblvious to Angelica's crush and was mostly spending time with Tommy and the others. It is possible that he may had felt an attraction to her, as seen in one attempt Angelica does to get him to like her, she jumps out and smiles approaching him. He gasps and nervously replies but tries to get away from her, its possible that he may have been too shy to really talk to her, he may had already liked her and was afraid to show it, or she just startled him by her direct approach.
Angelica is finally able to get his attention after she and the babies stage Spike to go wild(although truthfully, they weren't able to and the only reason he got wild was because a bee stung him), to which Dean rode on his bike and was able to save Angelica. Afterwhich, Dean slowly falls in love with her, saying "Hey Angelica, you're kinda nice. For, a girl I mean." Dean spends a good time then wooing Angelica by singing his "ABCs" and reading her a poem. He admits to Angelica that he feels an intense feeling around her, and both lean in to kiss. But before they do, Dean hears a woman calling him. As he tells Angelica bye, she asks "Is it another woman?" to which he answers "Yeah. My Mom" and rides away home with his mom. Angelica is left heartbroken but goes back to her old ways and even finds a new interest in Jean-Claude, her new neighbor.
Dean is a friendly, and willing to learn a lot of things. He is also in a way philosophical in his own way, which he credits to the book "The Cat In The Hat" for changing his life. Dean is seen later at Angelica's birthday party. Dean's name and manerisms may be a parody of James Dean who was the star of the film "Rebel without a Cause"