Grayson family employee and one of Emily's closest friends. Ashley betrays Emily to attempt to gain the trust of Victoria Grayson, but is unsuccessful. Initially working as Victoria's party planner and assistant, Ashley becomes the Grayson family spokesperson during Daniel's murder trial. After Daniel's exoneration, Ashley is employed by Conrad to work at Grayson Global and also serves as Emily and Daniel's wedding planner. After a failed relationship with Tyler Barrol and his murder, Ashley becomes romantically involved with Daniel. During the course of Season 2, Ashley was revealed as a sex slave for money in 2006, only to be saved by Emily Thorne. After Emily sends a scandalous video to Victoria of her tryst with Conrad, Victoria forces Ashley to seduce Salvador Grobet for his vote to Conrad, which leads to Daniel learning of Ashley's double-crossing, and ending their relationship. She has since forced herself back into the Grayson family by blackmailing Conrad in order to work for him during his governor campaign. Ashley later takes part in helping Jack with his revenge plan against Conrad near the end of the season.

In the season premier of season 3, Ashley tries to blackmail Emily into helping her stay in the Hamptons by introducing her to rich men. Emily, seeing Ashley as a threat, frames her for reporting falsely claims against Victoria and is forced to leave the Hamptons by the end of the premier.