9. Taylor Swift
It’s amazing to think that singing sensation Taylor Swift is only 27. She’s seemingly been around for ever, and her hit songs have resonated with audiences worldwide. Aside from her superstar status and the vast amount of wealth she’s accumulated, she’s also put together quite a dating list. For a 27-year-old, she’s dated an awful lot. Jake Gyllenhaal, Taylor Lautner, Joe Jonas, Harry Styles and Conor Kennedy make up just a snippet of that list. But she’s young, is rich, and is enjoying herself – who can blame her!