Skip to main content

Products purchased through this post may earn us a commission.

Coffee Talk

Reflecting on (and laughing at) our most awkward looks, habits, and phases.

coffee talk awkward phases

If you're anything like us, you grew up imagining a version of how middle school and high school was supposed to go—notes from crushes in lockers, prom, the best parts of Breakfast Club—then reality hit, and by that we mean: braces, acne, uniforms, puberty, chaperoned school dances, and unfortunate fashion choices. Below we're sharing our most awkward phases which, to nobody's surprise, peaked at 6th grade: 

Emily: My middle school years still haunt me. To give you some context into where I was emotionally, I'll go back to my first day of 6th grade. I remember going outside for recess, where everyone had divided into groups of guys and girls and begun flirting. I, on the other hand, had already booked it toward the somewhat sad-looking metal jungle gym that was empty. It was only until I was hanging upside-down from the monkey bars by myself did I realize nobody else was coming. Things didn't ever get that much better in middle school, culminating perhaps in my first "fashion-forward" outfit a couple of years later. Even though I still lived in my soccer uniform, I religiously read the dELiA*s catalogue that came in the mail each month. I couldn't afford to buy any of the tomboy-chic apparel that I lusted after (all of my babysitting money went straight to the bulk candy at The Sweet Factory), so I decided to do the next best thing: hit up my local thrift store. Since I truly didn't know what I was doing, I decided to invest in some men's trousers in order to achieve the look I was going for. The stained pair I took home was roughly three sizes too big, but I proudly paired them with a smiley face crop top, some strategically placed butterfly stickers on my cheek, my color-coordinated braces, and frizzy hair. 

Geoffrey: I know I'm not alone when I say junior high was holistically, my most awkward phase. Going through the early/mid stages of puberty is rough on everyone, but I'll point out some highlights: 1) I grew three to four inches over the summer between 6th and 7th grade, so my posture and coordination was similar to those inflatable, waving airdancers you see outside of used card dealerships. 2) Some guys are lucky when they get their first facial hair, in that it grows somewhat evenly around their beard line. Mine decided to solely sprout up between my eyebrows, bridging a gap that didn't need to be bridged. 3) I'm pretty sure I was still playing Dungeons and Dragons, which is now kind of retro-cool thanks to Stranger Things, but that was not the case back then. 4) I had this pair of shorts that I wore almost every day, one leg was green, the other was yellow. I know it sounds benign, but just think if you were wearing a pair of pants with those colors right now. You'd look like a clown school dropout.

Alina: 6th grade was the height of my nerd-dom. I went to an all-girl's Catholic middle school with a uniform. Our uniform was a black-watch plaid kilt—the heavy, wool, pleated piece that bagpipers wear in Scotland. To make it "cooler," all the girls "rolled" their skirts, which meant they rolled the waistband to make it shorter. I saw absolutely no merit in this folly, and for awhile, couldn't even comprehend why anyone would want to make a skirt shorter. Up top, all the girls kept their polo shirts unbuttoned down to the third button, not to show skin as much as to wear a polo shirt like a normal human being. I was apparently intent at this time on looking as nun-like as possible, so I kept my polo shirt buttoned up to the very top button—an exceedingly un-cool look. For footwear, all the girls wore ankle socks or no socks with their loafers, while I, on the other hand, voluntarily wore a tall white church sock. I decided it was cool to take the literal definition of "penny loafer" to heart, so I put actual pennies on the tops of my loafers. I wore my hair slicked down the middle in a harsh middle part, and my ears were kind of big for my head so I had a bit of a monkey-ear situation going. Lastly, I wore a "laptop backpack" that looked like a small house and was, in all honesty, the single nerdiest thing a 12-year-old has ever worn. The "cool" thing at the time was to have a slouchy, colorful, monogrammed L.L.Bean backpack nonchalantly hanging off one shoulder like you were the teen heartthrob in a CW series; and I made my way through the school with a a foot-wide, all-black technical-looking tank on my back that I proudly wore with both straps snug to avoid future back problems. I sang in an ensemble called "The Children's Chorus of Washington," (spoiler alert: it wasn't cool) that required me to wear a wool vest over my polo shirt some days. So picture me, strolling down the halls, with my top button choking my neck, chorus vest, long kilt, and laptop backpack forcing good posture, high-fiving teachers on the way to class. I wasn't even embarrassed or self-conscious, I was like: "mock me all you want, fools, this backpack is hilarious." My friends and I still laugh about 6th grade Alina to this day. 

Leslie: Like Emily, I hit the transition from tom boy to boy-crazy girlie-girl in 6th grade guns a'blazin'. I didn't hold back on either, which made for an interesting combination. I was a dedicated member of my middle school wrestling team (my claim to fame is that I made State, but also had to wear a skull cap at competitions so my long hair didn't get pulled), and wrote diary entries—this is a direct quote—like this, "Oh em gee [ed note: actually wrote "oh em gee"], Alex is totally going to be my first kiss. I'm wearing Juicy Tubes every day just in case." In case you need a reminder, Juicy Tubes are a tacky, ultra-shiny lipgloss that are the consistency and stickiness of honey, so you can't go 10 seconds without a strand of hair getting plastered to your lips. To make matter's worse, I had hot-pink braces (with matching rubber bands, of course) to fix the fact that my two center buck teeth didn't want to hang out with any of my other teeth and a Land's End uniform with a below-the-knee skirt. Also I went to school with the same 16 people (give or take a few) from 6th grade to 12th, which is basically an 8-year sentence to being incredibly awkward. I can't even begin to tell you how painful our prom was.

Products purchased through this post may earn us a commission.