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.

Casey, Chuck and Sarah are sent to Morocco to rescue Roan Montgomery. Morgan plans to meet Alex's mother and Mary spends some time with her family.