J and J start the show with a preview of tonight’s live show from Chicago. At 9:10 they discuss an argument that was set off by a dangerous hypothetical question. At 25:20 the Awkward Sexual Encounter involves a lost condom and a ruined set of sheets. Should you come clean when the condom gets lost in the most embarrassing place possible? At 35:15 a listener writes in to ask if it’s normal that her boyfriend has paid strangers for nudes on Snapchat. Does it count as cheating if he’s getting pictures from amateur porn stars? At 50:20 another emailer asks if she should be alarmed that her fiancé asked if the deposits for their wedding are refundable. Does this mean he’s having second thoughts about marriage or just asking an honest question? At 1:14:20 they rank the best and worst months of the year to be single, then close out the show with a round of Red Flag or Deal Breaker. U Up? LIVE is coming to the New York Comedy Festival on Friday, November 8th! Get your tickets by visiting betches.co/nycf