10. Nick Cannon
The singer, host, rapper, comedian and whatever else he is, says that his first time was unintentionally funny (not to him but to the girl he was with and her friends after she told them about his horrible skills). Cannon says that he tried to get down in a sleeping bag but he failed. Afterwards, “she ran into the bathroom with all of her friends and they were in there laughing. I vowed from that day forward no woman would ever laugh at me in the sack again. I actually ended up crying at the end of the whole ordeal.” Yikes, that is both sad and awkward.
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