5. Sarah Silverman

In a personal essay, Sarah Silverman described in great detail about the time she lost her virginity. After going home with the emcee of an open night mic she worked at, Silverman allowed “Kevin” to walk her through her first time. Initially nervous, Silverman felt proud after making it unscathed through her first sexual encounter. However, when her new lover pulled back the sheets, it revealed “a Rorschach-like pattern of blood. Like a red butterfly stamp, getting lighter and lighter with each imprint.” Following an incredibly long, awkward silence, Silverman hilariously remarked: “That came out of you.” Silverman claims his only response was “Um. No it didn’t. It’s OK. Just buy me new sheets.” At least he was understanding…

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