236 The Big Bang Theory The Tangerine Factor 01 17 2008-05-19 Comedy / Romance Jim Parsons - Sheldon Cooper / Johnny Galecki - Leonard Hofstadter / Kaley Cuoco - Penny / Kunal Nayyar - Rajesh Koothrappali / Simon Helberg - Howard Wolowitz / Melissa Rauch - Bernadette Rostenkowski / Mayim Bialik - Amy Farrah Fowler / Laura Spencer - Emily Sweeney / Sara Gilbert - Leslie Winkle / Kevin Sussman - Stuart Bloom / John Ross Bowie - Barry Kripke / Carol Ann Susi - Debbie Wolowitz Penny's break-up spurs Leonard to summon up the courage to ask her out, and each head to Sheldon for advice on their upcoming date.