Jennifer Love Hewitt

Jennifer Love Hewitt's worst date included some awkward gifting. “I went out with a guy who's a little bit older. I was 25 at the time, and he brought me an ‘N Sync T-shirt,” she said. “Am I, like, 12? Most guys would bring flowers or chocolates. He also gave me Altoids for our kiss at the end of the night, and we'd barely said hello. I found that so grody.” Amen, sister. [Music Rooms]