The Evolution of Sideboob

By Catherine O’Sullivan

On a tier above and adjacent to us, a group of noisy USC students are celebrating something. I have no idea what. A twenty-something blond with a broad back pivots in her chair, flashing serious sideboob. I point this out to my dining companion.

His head pivots 180 degrees and when it comes back around his mouth is hanging open. “Don’t be so obvious. At least pretend like you’re looking at the wine list.” Said list is chalked up on the board behind the revelers. They have Verdugo and Andalusio, Toro and Spaino and loads of other vintages all from the sun-soaked plains of that land overseas that just missed inventing tortillas. It could have become a great civilization but for that.

He gives it another go, turning his head more subtly this time. The Catalonia Picado is a very spicy vintage, no doubt… and man holy shit, you can almost see nipple. Blond locks flowing, hiding the knot at the neck of the flimsy black halter dress with a back so low it’s possible there’s no dress at all.

Something happens. The students roar. Their conversation is mostly roars. In the high ceilinged, quaint-in-a-rustic-sort-of-way-restaurant, the decibel level soars. “The scallops are really good,” hollers my companion. Finished with gawking, he is back to thinking with his second favorite organ. I can barely hear what he says, cupping both ears like radio dishes trying to receive faint signals from outer space. My efforts are futile, though, and I am forced to read the menu. The scallops are grilled in a number of things, most of which I’ve never heard of—including carrot goo.  I order them.

Sideboob sips her drink, moves closer in and cuddles her boyfriend, flesh barely teasing his upper arm. She whoops about something as he whispers in her ear. I don’t blame her, really. Young, well-fed, and cultivated as if raised on a cage-free farm for beautiful girls: she should be whooping about everything. The world that unfolds for her is not the same one the rest of us muck around in. It welcomes and embraces her gently and lovingly. Everybody in it is “nice.” It puts its coat over puddles in the road lest she dirty her Italian slave sandals.

Sideboob is only just emerging, almost certainly a twenty-first century invention. Thousands of generations of women all over the world have launched endless assaults with cleavage, but millennials have come up with sideboob all on their own.

I imagine the dilemma—how to both show and not show off a pair of magnificent breasts—first presented itself back in the prehistoric era. Some woman (probably a blonde) used her big, well-formed breasts to land the best caveman of them all. He really liked those breasts, but he didn’t necessarily want any of the other guys to get a look at them—even though most of them already had. (The best caveman wasn’t necessarily the smartest. He was just the best at hunting and running and grunting.)

Perhaps the conversation went something like this: “Now that you’re going to live in my cave,” said the Best Caveman, “you’ve gotta cover those things up.”

The Best Caveman’s woman was not thrilled by this pronouncement. She had a baby who ate ten times a day and constantly taking a yak pelt on and off seemed like a pain. “What if,” said the Cavewoman, thinking on her feet, “I cut a ‘V’ in the top of the yak pelt. That way when the baby needs to eat, I can just whip out a breast.”

This idea caused the Best Caveman some degree of consternation. A full time crew-neck yak shirt was a heavy burden to bear, but it would still allow all the other cavemen to see the smooth, creamy swell of her breasts. Of course, it occurred to the Best Caveman that maybe, just maybe, the only parts that really mattered were the nipples—he and the baby were both fascinated with them, after all.

“Okay, fair enough,” said the Best Caveman. “But if you pull those things out when the second best caveman is around, I’ll club you insensible.”

“Grunt,” said the Best Caveman’s woman.

Ever since, women have found hundreds, perhaps thousands, of ways to exploit this initial, and for reasons unknown, definitive masculine decree as to the permissibility of cleavage. By the time the 20th century rolled around, women were well aware of the fact that cleavage can be an enormously powerful tool in making men act the way you want them to. Displayed correctly, cleavage could poleaxe almost anything with a Y chromosome, leading to free drinks and eventually even new furniture for the living room.

But then something happened that no one could possibly have anticipated: breast implants. Breast implants made cleavage so common it got boring. Everybody had massive cleavage: children, fat boys, young girls, old girls. There were fifty- and sixty-year-old women walking around with the tits of twenty-five-year-olds. The entire competition had to be tossed out. And that’s where the genius of this latest generation comes in.

While breast implants look great from the top—round, boisterous, symmetrical—the sides are just, well, a bit of a let-down. Fact is, you can’t fake awesome side boob. One glimpse, and you know you’re looking at blobs of manufactured plastic. The girl at the restaurant knows this; that’s why she’s flashing what she’s got. It’s the real stuff.

The students roars again. Someone’s ordered a round of drinks, something trendy and strong and terribly, terribly pink. It’s either watered down Nyquil or something obscurely Spanish. My dinner arrives. The scallops are decoratively arranged on a bed of carrot goo and grilled to perfection.They are delicious.

Catherine is a writer, former journalist with the Tucson Weekly, and last year’s Annenberg Scholar at the University of Southern California.  She’s got 2 grown kids, a dog called Sadie, and is currently working on a non-fiction narrative about women and horses.  She lives in Tucson, Arizona.  More of her work can be found at


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