Complex sentence: In 2013, Rae began working on a comedy series pilot with Larry Wilmore about the awkward experiences of a contemporary African-American woman, in which she will be starring, eventually titled "Insecure".
Split into simpler sentences: In 2013, Rae began working on a comedy series pilot (in which she would star) along with Larry Wilmore. The show was planned to be about the awkward experiences of a contemporary African-American woman; the pair eventually settled on the current title of "Insecure".