8. Shia LaBeouf

In an interview with Playboy Magazine, Shia LaBeouf retailed his first time having sex. At age 18, LaBeouf sealed the deal with a close friend of his. In his own words, LaBeouf stated that, “For some reason, I was trying to portray myself as a man who had done it many times in the past. I didn’t tell the girl I was a virgin.” In an effort to prove his manliness, LaBeouf attempted to mimic moves he had seen in pornos. He recalled putting a pillow underneath her which “put her at a weird angle, where I couldn’t get in correctly. I’m not extremely well-endowed.” Although LaBeouf’s recollection may sound awkward and self-deprecating, the actor assured readers that he went on to date the same girl and had a lot more practice with her in the future.