8. TAYLOR SWIFT Why should Hef date T-Swift? Well, why does any guy date her? Immortality. Even though he has the entire Playboy empire as his legacy, the most enviable guy on Earth is still missing one thing: a Top 40 Billboard hit entirely dedicated to him. Plus, with her height, blonde hair, and the fact that her name is Taylor, she seems like a Playmate-in-the-making to us already.