The guy on the phone today is willing to tell us the MOST EMBARRASSING date night of his life… in hopes it will get him another shot with the woman he loves. Will it be worth the humiliation? Find out in the Second Date Update!

Second Date Update UPDATE: A Whole New Girlfriend
18:20

Second Date Update: The Sobfather
18:43

Awkward Tuesday: A Rabbi Walks Into A Bar
18:25