Thirty-year-old infamous New York socialite Justin Ross Lee owns a line of fancy suit pocket squares called Pretentious Pocket. Justin, who became a minor internet celebrity for being a narcissistic troublemaker, is looking for his own Kate Upton to join him in his life of travel and adventures. Patti’s second millionaire is thirty five-year-old Michael Sartain, a “geek-at-heart” and a former Captain in the Air Force who now owns a PR firm in Las Vegas. Will Patti get Michael to lout out his “inner geek” so he can find his true soul mate?