Rick Rosner opens with a cheeky challenge: in a bar of sixty-year-old women, he claims he would leave with a date faster than Grigori Perelman. Scott Douglas Jacobsen grounds the banter with facts—Perelman proved the Poincaré conjecture, declined the Fields Medal and Clay prize, and lives reclusively. The duo calibrate odds, debating five-eighths versus nine-sixteenths while teasing variables—American versus Russian patrons, shared Jewish background, flirtation strategies, and Rosner’s past as a stripper. The exchange is a playful thought experiment about charm, fame, and probability, not a moral treatise, balancing irreverent humor with precise references to mathematics, awards, and cultural nuance.