TYRA BANKS

Tyra Banks was the supermodel in the 1990s and early 2000s. From iconic magazine covers, to unforgettable runway performances and even her own television ventures, Tyra has pretty much conquered it all by 38. But, for the most part her romantic life has been kept private. Which means unless paparazzi catch her out on a date, you're not going to hear about very many details. Although she has been romantically linked to dozens of rich and famous suitors, only a handful of those connections have any validity. Most recently, it has been reported that Tyra has been dating Drake, 25. The two were spotted enjoying each other's company at Disneyland in California a few weeks ago, but nothing has been officially confirmed.