The Moment I Knew I’d Never Be Cool

The Moment I Knew I’d Never Be Cool

From Chicken Soup for the Preteen Soul

The Moment I Knew I’d Never Be Cool

From their errors and mistakes, the wise and good learn wisdom for the future.


My older sister was born to be liked. She came out of the womb with a cute face, blonde hair, a sense of humor, athletic ability, and what my mom called the “gift of gab.” She went through her childhood with lots of friends, lots of parties and lots of attention. I wanted what my sister had: popularity.

I studied her for years and never came close, so I turned to kids my own age for role models. Jen, the girl I always sat next to in school, threw her blonde hair around, showed off her dimples, put her head to one side when she asked for favors and was easily voted most popular in class. Okay, I thought, I’ll try her tactics. I threw my brown hair around, smiled without dimples, put my head to one side and asked my teacher for a pass to the bathroom. She looked at me and said, “Why are you doing that with your head? Don’t you feel well?”

That was my cue to try for cool instead of popular. I’d do anything to escape my lack of social status. Cool kids always acted as though they had the world under control, maneuvering around obstacles and adults with ease, and never cracking under pressure. My big chance came when a new girl moved to town and into my class. Nothing seemed to ruffle Tiffany. She was cute, trendy, and best of all, she liked me.

Our friendship lasted four weeks—just long enough for me to learn that Tiffany took European vacations, went skiing in Aspen and bought clothes at Nieman-Marcus. I’d never been outside of Illinois, on skis or anywhere but the Sears preteen department. We were only eleven and she’d already picked out the car she’d get for her sixteenth birthday. Tiffany was way too much for me. I crawled back into my familiar invisibility. . . .

Until I met Mandy. Mandy’s middle name was “rebel.” She and her brother, Kevin, smoked cigarettes and stole money out of their mom’s purse. If popularity and cool are out of reach, I thought, I’ll take rebellion over facelessness. I was soon hanging out at Mandy’s house, where no adults were ever around to notice what we were doing. I puffed cigarettes, pretended to shoplift and felt powerful for the first time in my life. I did crazy things my parents never suspected, and had a great time bragging about it to other kids. I could feel my status rising. Then Kevin was arrested and sent to a detention center. Never wanting to end up like him, I pitched my cigarettes and headed back into obscurity.

By eighth grade, I was desperate. I tried out for cheer-leading at my small school, and by some miracle, made it onto the squad. My head swelled like a melon. I must have absorbed popularity and coolness without realizing it, I thought. I took this tiny piece of status and ran with it.

At first, being popular and cool seemed to be easy. I tolerated, agreed with or laughed at the nasty comments of the cool girls who stayed that way by pointing out the uncoolness of others. Things like, “Look at Dana’s hair. Think she used a hedge trimmer?” or, “Can you believe those shoes Lauren wore last night? She must have borrowed them from her grandmother.” Guys weren’t spared. “Oh, Tyler. What a crater face!” and, “Yeewww. Bryce actually thought I’d be seen with him in public!”

The better they were at cutting people to shreds, the faster those girls seemed to rise above the masses. Like stand-up comics, they pointed out other people’s flaws and made the crowds roar. Why, I wondered, were put downs cool? They made my stomach cramp. Was it who said them? The way they were said?

Okay, I decided, I can say nasty things about other people for the sake of personal success. I picked a time and place for my initiation. A budding friendship with the Faris twins gave me a stage. Sara and Shauna were way cooler than I’d ever be. They’d been hanging with guys since seventh grade.

My debut came after church. The three of us were standing around waiting for rides home. I listened to them rip first on girls and then on guys. One guy in particular took the brunt of their hits: first his clothes, then his voice, then his brain, then his looks.

“I know what you mean,” I volunteered, as Shauna turned up her nose at the mention of the poor guy’s hairy arms. “Some guys are real apes. . . .”

As the words left my mouth, a not-so-good-looking guy drove past in a blue convertible. Perfect opportunity, I thought. I pointed to the driver, “. . . like that guy—red-haired and u-g-l-y.” I made chimp sounds as I watched the car turn into a nearby driveway. Instead of agreement, I heard nothing from the twins. It was like I was standing on the ocean bottom with my ears plugged. I turned slowly to see Sara and Shauna with necks stiff and eyes impaling me on an invisible stake.

What? What? my confused brain was pleading. What’d I say?

The answer slithered out of Sara’s mouth as the twins turned their backs and walked toward the blue convertible. “That red-haired and u-g-l-y ape is our brother.”

The rest, as they say, is history. My journey to cool stalled right there in front of church. With face burning and ears ringing, I’m sure I heard an otherworldly voice whisper, You’ll never be popular, cool, or anything else your heart won’t let you be. Start looking inside, instead of out.

It took me a while to get what those words meant. But once I stopped trying to be like other people, life got a whole lot easier. I’m even growing up to be someone I really like.

D. Marie O’Keefe

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