Jim Rutledge and Matt Hamilton roll into the heartbreak hour of their Valentine's Day show. Following Evan Cohen's appearance and with his shared distaste for this "hallmark holiday", Jim makes the case that Valentine's Day isn't even the worst day to be dumped on/before. Jim, Matt, and producers Primetime and Krissy discuss the worst holidays to get dumped before. Prime shares his expertise as the extremely single guy on the show. They continue discussing heartbreak with today's Siding Unlimited poll question -- Which Wisconsin sports team left us the most heartboken after failing to meet expectations: the 2011 Packers, 2011 Badgers Football, 2014-15 Badgers Men's Basketball, or the 2008 Brewers (aka the CC Sabathia team)? Which program/franchise is most unlikely to ever get back to a championship (aka Badgers basketballl..)? They play Molly's Game, and Molly Brown really phones it in with her NBA All-Star weekend props and lines. They go Poll Dancing, answering questions about Valentine's Day traps and the most important piece of good sub sandwiches. Matt wraps up Valentine's Day by describing the dazzling details of the dinner he's gonna make for wife Jen, brought to you by Metcalfe's Market!