Rob was Natasha's boyfriend in high school; they dated for eight months and four days. They began dating after Natasha helped him in their AP Physics class, and Natasha generally liked dating him. He cheated on her with a blonde girl named Kelly. In the present, Natasha finds that his qualities she once found charming—specifically, his smile and his ability to convince his partner of his virtues—now seem stupid and shallow, and she can't fathom why she ever liked him.