In her opening monologue, host Chelsea Handler talks about how she celebrated Valentine's Day. Chelsea and her round table panelists Chris Franjola, Emily Heller and Ian Karmel discuss Charlie Sheen getting engaged to a porn star and wanting to have more children with her, and the decline in the number of clowns worldwide. Jen talks about what has now become her new Valentine's Day tradition based on what happened on the day this year. The latest episode of "Judge Lately" is presented featuring a case between mother and daughter, defendant Kris Jenner vs. plaintiff Khloé Kardashian. And Chelsea chats with guest Alex Pettyfer about his latest movie Endless Love (2014), his and Chelsea's encounters during parties, his British background, why he doesn't drink, clearing up misconceptions about a hit and run story involving him, and a proposition that Chelsea makes to him.