Chuck needs to go undercover to seduce a woman named Sasha Banachek, so an old school spy named Roan Montgomery is assigned as his mentor. Meanwhile, Captain Awesome finds himself in need of some relationship advice, and and turns to Morgan, and Lester faces his first problems as assistant manager.
Quest roles:
Bonita Friedericy(Diane Beckman), John Larroquette(Roan Montgomery), Matt Bomer(Bryce Larkin), Melinda Clarke(Sasha Banacheck), Matthew Jayson Cwern(Handsome Cool Guy), Manny Hernandez(Messenger), Sarah Poynter(Stewardess), Nathan Sutton(Agent Epstein), Mark Kubr(Thug #1), Adam Sauter(Employee), Tammy Dugen(Applicable female in electronics), Jason Collett(Buy More Employee)