Lena Dunham

Premiere Of Universal Pictures' "This Is 40" - ArrivalsSOURCE

Actress and author Lena Dunham lost her virginity when she was fairly young. But the worst part wasn’t how awkward the experience was- she claimed it was very awkward for both her and her male partner. But she was walked in on by her friend, who shouted “Mazel Tov” when she realized what the two of them were doing.