Reed Fish (Jay Baruchel) is living the life he was meant to. He's a small-town, radio talk-back host and he's engaged to the gorgeous Kate (Alexis Bledel), but everything gets a little topsy-turvy when his high school crush comes back to town. Everyone thought Jill was at law school, but it turns out she's been waitressing and trying to get a music career off the ground - without much success. Reed encourages her to pursue that dream, but the attention he's paying Jill begins to interfere with his relationship with Kate. A quirked up rom-com that also features fine support from Katey Sagal and Chris Parnell. Writer Reed Fish (no it isn't autobiographical) has a cameo as a character named John Penner.
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