First-time guest, Caleb Masters, helps Nathan break down the laughter and heart of the number 21 film on the 50 Best Rom Coms list, ‘The 40-Year-Old Virgin.’ Plus, Whitney drops in to give her quick take on the film and help celebrate a huge milestone—our 100th episode!

Nathan and guest, Andrew Hudson, strive to be better than the Gap as they review number 35 on The 50 Best Rom-Coms list, Crazy, Stupid, Love.