An expert on the dynamics between men and women, Damon Salvatore knows his uptight new publicist could use his help getting a date. The only problem is, the more time he spends with her, the more he realizes he doesn't want her dating anyone but him!

When a new teacher starts at Mystic Falls High Elena finds herself attracted to him. As this attraction grows Elena finds it harder to keep her mind away from the teacher, who just happens to be her boyfriends brother.