Retired at 35 S02 E04 The Grifters

David meets a nice girl named Jenn (Danneel Ackles) at the grocery store, and lies to her about his career and financial situations. Alan and Elaine become convinced that Jenn is hiding ulterior motives with regards to David. Amy and Jared agree to move in together, but after Amy gets advice from Alan about the decision, Amy scares Jared about possible marital commitments.