Who Here Is Embarrassed by the Person They Lost Their Virginity To?


Breaking: Brooke Shields lost her virginity to Dean Cain. With this as our emotional mooring, let’s all take a minute and now think about who we lost our virginity to. How mortifying is the memory, on a scale of 1 to 10 billion?

Dean Cain is not my type, not even sort of. I’m trying to imagine if I’d have wanted to get with him if he’d gone to my school, and I’m thinking that his symmetry and buffness would have been unbearable when my idol was a pasty, lipstick-smeared Robert Smith from the Cure—who was, and is, as far as I still know from the fan club newsletter, still married :/

That said, Dean Cain is not an embarrassing admission by most standards! But people regret their virginity loss for a variety of reasons, and it appears that Brooke Shields is no exception. From an E! Online report:

Have you heard Brooke Shields‘ confession yet? She lost her virginity when she was 22 to the one and only Superman aka Dean Cain!
It’s a personal story you’ll read all about in her new memoir There Was a Little Girl: The Real Story of My Mother and Me. But before you expect plenty of friction and animosity between the former couple today, it turns out the pair still has deep love and respect for each other.
“We are still great friends…I was in love with her certainly, we were in college, sweethearts,” Cain shared on Monday’s all-new Meredith Vieira Show. “There was nothing I did to her that I’m ashamed of in any shape or form. So I said [to her] write away and hopefully it will be cathartic for her and she can sort of deal with that huge portion of her life.”
Huge portion may be putting it lightly.

When I first read that last line I thought it was a Dean Cain dick joke. But no, it was a nod to how Brooke Shields had taken a public vow of chastity and felt like “America was watching,” and also her mom was super religious, and so she naturally felt guilty after giving it up to Buff McSymmetry.

But Brooke Shields can say something I can’t: That she became a woman with a guy who would go on to play Superman, whereas the dude I lost my virginity to was fond of doing 360s in his Camaro in half-empty parking lots, then coming up to me afterwards to laugh dumbly and say, “Huh huh, I done a donut.”

I done a donut.

I done a donut.





I bet at no time under any circumstances has Dean Cain ever uttered I done a donut. Dean Cain comforted Brooke Shields after they had sex because she felt super guilty about doing it, and ran off buck naked, but he followed her and they talked and then they chilled out and it was fine and he would like everyone to know that he thinks she’s still great and everything, even now, and just a wonderful person and stuff.

Very nice for them. Hey, just wondering, has your boyfriend ever done a donut?

I asked some friends if they’d lost their virginity to any equivalent of a donut-doer (pun intended), and although none of them had ever even had to know anyone who ever done a donut, some of them were indeed embarrassed by their partners in first-time sex-having.

One woman explained that, hey, listen, she did the best she could with the 50 eligible people at her tiny high school (none of whom told her about any donuts they did). But still, she was mortified because:

just his basic personality and everything. this was the high school boyfriend who i tricked into the army and was a drug addict and in a mental institution and carved my name in his chest. He had plugs in his ears and dyed his hair cherry red.

Another lady said she was embarrassed because it was a guy two years younger on the debate team and even dorkier than she was. Another said her virginity taker “didn’t amount to much.”

he was not smart but he was cool and funny and cute. he also had this beautiful vintage baby blue F-150 with a bench seat, given to him by his grandfather, so I was like “put it in me”.

Another woman who had lost her virginity twice—to a man and a woman—said that the former was sweet and the latter was annoying, but neither was embarrassing.

A man said he lost his virginity and was “‪was just excited to be wanted.”

Obviously, losing one’s virginity can go any number of ways. It was nice to hear from this random unscientific poll that these first times were not necessarily embarrassing, and not even that bad per se. I, however, still feel a sheer and unforgettable donut-doing mortification about the person to whom I lost my virginity. What say you?

Image is Hans Holbein the Younger. c. 1517

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