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.

Grey’s Anatomy Season 6 Episode 19 “Sympathy for the Parents”: Promotional Photos!
Gossip Girl Season 3 Episode 16 “The Empire Strikes Jack”: Promotional Photos!

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His little love fests are getting really boring