After Hef lands another major milestone at "Playboy," the Girls are inspired to pursue their own careers. Bridget decides it's time to put together her demo reel to help her get some hosting gigs, but is she seasoned enough to snag a permanent on-air spot? Meanwhile, Kendra heads to San Diego with her agent to scout out real estate for a long-term investment. Will she be able to find the condo of her dreams? And the pressure's on Holly when she apprentices with a "Playboy" editor for a centerfold pictorial. Can she step up to the plate--or will she find herself in over her head? And more importantly, will Hef like her final product?