S1, E3: Jason, a 33-year-old film director from Sandusky, Ohio, has dreams of a true Hollywood romance, complete with a Pam Anderson-type for his leading lady. After a string of failed dates with the typical California blonde bombshell, will he follow his friends' advice and open his heart to a down-to-earth girl from the Midwest? Matt, a 27-year-old millionaire, uses online dating to find companionship while on the road for work. This self-proclaimed player uses a mass-marketing approach, sending dozens of women identical messages to make sure he doesn't spend the night alone in his hotel room. Will his strategy pay off or will he crash and burn when he books three back-to-back dates in one night?