When Will and Ashley are in her room, Ashley comments that she's old enough to marry Jerry Lee Lewis. This is in reference to Lewis's controversial 1957 marriage to Myra Lewis (nee Myra Gale Brown), who was just 13 years old when they married while Lewis was 22.
Ashley's room has a poster of Tevin Campbell on the wall. Campbell appeared previously as Ashley's first date, a popular young music artist named 'Little T' in season 1, Just Infatuation (1991).