Soon. TV Guide says that once Jen and Ryan hit the skids, he’ll rebound with a very interesting woman. She’ll entertain him with her colorful stories of the good old days; he’ll totally freak out once he realizes that he’s sleeping with the mother of one of his students.

Guest Star Spoilers: Grayson’s Getting a Girlfriend…Guess Who?
Spoiler Scoop: Going To Love The Third Episode Back
Vampires Diaries: To Be Renewed
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His little love fests are getting really boring