Drake Sits Front Row at Serena Williams's Fashion Show, Manages to Charm Anna Wintour

Drake can work his charm on just about anyone, including the notoriously formal Anna Wintour. The rapper sat front row at rumored girlfriend Serena Williams's fashion show at New York Fashion Week on Tuesday, and things took a surprisingly giddy turn. Drake sat next to Vogue's editor in chief, and while he respectfully stayed quiet during most of the show, he couldn't help but entertain Anna at numerous points. The two were spotted cracking up with laughter and whispering funny things into each other's ears.

The rapper's cute outing comes on the heels of Serena's US Open loss against unseeded Italian player Roberta Vinci. Drake was on hand to watch the tennis player in action, but the Internet was quick to blame him for the heartbreaking defeat. Keep reading to see more of Drake and Anna's antics, and then check out his failed attempt at playing backyard soccer.