Me, Myself and My Inferiority Complex Around Teenagers

Someone please tell me who ran off with the awkward phase.


This morning Harling, our Social Media Editor, told me she received a thank you note from a 15-year-old family friend. It came in the form of a text message and accompanying selfie. So casual-cool, right? It feels like just yesterday that I was printing my thank you notes on the floral paper my mom kept above our rock of a family computer and addressing them in my personal font flavor of Curlz MT.

But actually, that was 2002. And I have a sneaking suspicion that teens today wouldn’t touch that kitschy printer paper with a ten-foot sticky hand. Why would they? Snapchat filters add more spice to the mundane than anyone ever needed.

Think-pieces on Generation Z (or the iPhone Generation or whatever you want to call them) are probably at peak reach right now — it’s almost like no one cares about the narcissism of us millennials anymore — but I’m not here to wax nostalgic about the death of youth or taxes. I just need to get something off my chest: I am in awe of and intimidated by today’s teenagers and, frankly, have spent more time thinking about them in the past month than I did when I actually was one.

It all started when I moved to New York, where every teen-aged person seems to have the drawl, gait and demeanor of a movie star at the apex of their career. When I see them I perform a gollum-esque combination of staring and cowering. What happened to the awkward phase? Mine lasted for about nine years. That’s a phase, right?

I declared this interest a “spiral” last Sunday, when I found myself 72 weeks deep on the Instagram account of Lily Rose Depp, the just-turned-17-year-old daughter of some old dude named Johnny. To be clear: I only stopped because I’d reached the end.

Her bio fascinatingly reads: “this is my only form of social media! all other accounts (twitter, facebook, vine, snapchat, blog, etc.) are FAKE!”

y'all said She'd look good if she were smiling 😂😂😂😂

A photo posted by Lily-Rose Depp (@lilyrose_depp) on

I mean, really: the great outfit, the flawless makeup, the casual expression, the ironic caption? 2003 Hillary Duff would never. Or would she? Maybe we wouldn’t know, because ten years ago our teen idols were just the smiling faces starring in our favorite shows or fronting our favorite bands. We could only describe them in as much detail as Teen Vogue had profiled them. Knowing them further was as unattainable as knowing them personally.

And this is the crux of it: attempting to embody a version of cool that existed outside of our hometowns was like interpreting abstract art. We were left to our own shoddy devices.

Do you think I would have spent three years wearing sparkly powder that was curiously stored in the handle of a makeup brush AS MY FOUNDATION if YouTube makeup tutorials had existed? Do you think I would have wasted time reading US Weekly if Rookie had been a thing? Or dressed as I did had ASOS or Nasty Gal or Topshop been at my 2-day shipping beck and call?

If I’d idolized and followed Lily Rose Depp or Amandla Stenberg or Evita Nuh or Kiernan Shipka or Yara Shahidi or Sofia Wolfson or Kaia Gerber or Jaira Miller, I can’t imagine I would have wasted so much time with a frame of reference so small.

And it’s not like cool is everything — it’s only one thing. An often shallow thing. But teenagers now? They have it. And not just the adolescent version of it, the real it. The cool kids in my high school wouldn’t even register on the richter scale today.

I hate to be so trite as to circle this back to the Internet, but maybe the accessibility it affords — to idols, to fashion, to the very things we arbitrarily define as cool — has enabled the teenagers to, if not find themselves sooner, then at least appear as though they have to the rest of us.

Right? Or was this just a long way of retro-justifying how lame I was ten years ago?

Feature photograph from Getty via The Telegraph; carousel photograph from Getty via Mirror


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  • Dani Heifetz

    As a normal, non-famous teenager, I feel the exact same way! I think it is so much more to do with the ability to present yourself a certain way on social media, along with the fact that all of these teenagers are pretty famous or at least afforded certain opportunities the average teenager in the suburbs doesn’t have. I do read rookie and I do shop at Topshop & Nasty Gal, but I am definitely still in my awkward phase!

  • Harling Ross

    I’m not sure my awkward phase has fully ended, leading me to ask myself, what exactly constitutes a “phase”–and can it be surgically removed, like a mole?

  • Marie-Eve

    Think-pieces on Generation X – I think you mean Generation Z
    but I’m not hear to… – you probably mean “here’?

    • Haley Nahman

      Bless you, sorry and thank you!

  • Yvonne Dunlevie

    Props to Lily Rose for keeping it real with only 1 form of social media!!

    • Yvonne Dunlevie

      But also, I made my Dad take me to see the Lizzie McGuire movie in theaters during a basketball tournament in Reno, Nevada. She was my idol. Not sure I could keep up with Lily Rose Depp today.

    • Haley Nahman

      I want to steal her bio even thought it’s not true!!

  • Beatrice

    I wore an orange T-shirt and track suit every day for most of 2001. That was followed by nearly 5 years of Laguna Beach-inspired loungewear. Decidedly uncool, but I’m hopeful that it made me a better person????

    • Haley Nahman

      It definitely did!

  • Maybe we absorbed all of the awkward for so long that there was no awkward left over??? Idk I’ll always be in awkward phase.

    • Krista Anna Lewis

      Or maybe everyone’s now on the same level of awkward bc of phones and IRL convos being rare so awkward is the new normal?!?! (or is it just me???)

      • Ooooo that’s a good observation. I always thought that if someone responds verbally with “that was awkward,” they’re not being funny and whatever happened was probably not that awkward. Is awkward a state of mind? Or being? I always associated awkwardness in person with lack of confidence or self ownership. the Internet definitely makes more awkward situations, especially when an email or text is ignored/forgotten even though we’re always connected to our phones. Right? Now I am thinking that talking in person is actually LESS awkward because it is refreshing to have a good conversation in person and, generally, if you get over being shy, no in person conversation can be awkward because in this case it’s more of a state of mino. Going thru puberty on the other hand…ALWAYS an awkward state of being. I’m cringing as I type this, my own embarrassing moments flash before my eyes. ?

  • Julie Meowmeows

    The Delia*s catalog and Seventeen magazine were my only frame of references to what was cool. Hell, I didn’t even have cable until high school. Dork dork dorky dork!

    • Haley Nahman

      Wait…should we start using asterisks as apostrophes? I*m down!

  • Trina

    I think I have a bit of inferiority complex when it comes to teenagers and social media and how “together” everyone seems… Then I get caught feeling insecure about feeling inferior to 15 year olds (talk about a vicious cycle) and remember that although I’m still caught in a perpetual awkward phase, I’ve gotten rid of the braces and am pretty okay with the weirdo I’ve turned out to be. They can have their finesse and perfect selfies, I’ll keep my grandma heels and clashing colors.

    • Krista Anna Lewis

      Grandma heels and clashing colors 4eva. TBH tho weirdos are way cooler than the cool kids.

      • Haley Nahman

        I wished I’d understood that more as a teen. Perks of Being a Wallflower made me regret all of high school.

  • olivia george

    As a fellow teenager said, a lot of us are in our awkward phases despite the public image that is presented on various social platforms. But! I think there are distinctions to be made within teenagers themselves. Me and my friends are seventeen and we’ve noted girls and boys younger than us, like 14 year olds, for example, are crazily “cool”. I still can’t apply makeup well, and it seems to us that they enter high school in the uk with makeup diplomas and makeup collections that are seriously expen$ive. Not as if that’s a bad thing, it’s just often envy of the essence of cool we find in people circulated within the teenage community very prominently, even by said cool people!!

    • Haley Nahman

      That’s so interesting — would love to learn more about how teens today feel about all this!

  • Isabel

    Just this weekend, I was Instalking my uber cool 17 year old cousin. I am 23 right now, but we are different because I am a run-of-the-mill Gen X’er, and she is the epitome of Gen Z. She is about to embark on her college career this fall, and I couldn’t help but think to myself: her college experience is going to be documented in this beautiful package that will outshine my outdated Facebook photos. Why do I care? I know I shouldn’t. But I am just so intimidated by her! Her Instagram has a perfect on-brand aesthetic that mine lacks. Her selfies hit three-digit likes in minutes. She’s had social media wrapped around her finger singe the beginning.

    So here’s my take: I think us Gen X’ers not only had an awkward phase IRL, but also on social. If I go back to some of my first pictures, I ask myself: Why did you post this close up shot of your PB Teen leopard print bed sheets? And THEN add a filter to the image? Why? Generation Z, however, waited by the sidelines as us babysitters and older cousins alike, screwed up. Gen Z’s secretly created a best practices and then began looking up to the super cool celebrities of their generation. They didn’t have to figure it out though, we did it for them.

    • marissa

      I think you might be confused about generations! If you’re a Gen X’er, you were born sometime around the 1960s-1970s. Millenials are roughly 1980-2000 (though I would personally cut it off a few years earlier), and then Gen Z is after that. So if you’re 23 then you are definitely a Millenial!

      But i completely agree about the pbteen sheets… *quickly purges old instagram posts from pre-2013*

      • Isabel

        Thanks for the correction! I totally mistyped gen x! But actually generation z has recently been changed and it now starts with those born after 1995. My cool cousin is the one that informed me haha

  • Hannah Cole

    I feel the same even about toddlers today – dressed so wisely and cool. I just went around in my matching leggings and sweater (which, to be honest, isd equally cool and wish I could pull off today)

  • Andrea Raymer

    This weekend I experienced a very exciting moment: my cool 17 year old cousin texted ME asking for instagram advice. Apparently she wants it to become an instagram model so she needed my help on branding herself.

    • Andrea Raymer

      Also, it is hard not to be intimidated when a cousin WHOSE DIAPERS YOU CHANGED has a boyfriend before you.

      • Haley Nahman

        I dont even know where I’d begin if a 17-year-old asked me for help on how to become an instagram model

  • Kelly

    When these kids are our age they’re going to be feeling the same about the new teenagers. It’s all cyclical.
    And to be honest, I am so happy that I didn’t spend my formative years with so much social media. I feel like it puts a lot of pressure on these kids to look or portray a certain image. When I was 15 I wasn’t worried about how many likes I got on a photo I was actually interacting with people face-to-face. I didn’t need to think about what kids in LA or NY were doing because everything didn’t move as fast and I could just think about what my friends and I were doing. We were our own definition of cool, before everything got so worldly and we realised we were just some kids in Australia.

    • Haley Nahman

      It’s a great point. I shudder to think of what my IG would look like if we’d had it back then. Haunting.

  • Olivia

    Honestly, even celebrities were super awkward in the early 2000s!! It wasn’t just us millennial teens! This slideshow is confirmation of their supreme uncoolness and is always excellent to bring up at parties:

  • Not Constantinople

    I teach high school. Trust me, the Awkward Phase still exists. They are just good at curating an image of themselves on social media. Outside social media, or, as I like to call it, Real Life, there are plenty of zits, greasy hair, questionable tastes in music, squeaky voices, insecurity, inexplicable mood swings, and awkward social encounters. I really feel for them, poor things!

    • kimithy

      THIS. Even on big, urban Uni campuses (I work at one), the level of teen awkward is so high. Their social media may look put-together, but in real life, they’re as bad as we were – over-the-top attempts at blase, overwrought emotional outbursts, supertrendy/unflattering fashion/beauty, earnest attempts at looking sexy and/or older, and all the other age-old trappings of puberty and immaturity.

      To me, some of the kids mentioned in this article as representing “cool” (e.g. Depp kidd) actually read suuuuper “trying too hard” (the antithesis of cool, and a hallmark of awkward adolescence). For every effortless-looking, stylish, “cool” teen I see out in the world, I see 20 normal, awkward ones squeaking and squealing and flailing just like we did 🙂

  • Aggie

    I take the bus to work in London and always end up seated next to the teenagers and I always ask myself where are the braces? The acne? The awkward outfits? But no they all look gorgeous and know how to dress, it may be a particular demographic but there must be some serious social pressure for all of them to look like that. I also wonder if because of the health and fitness trends going on right now, they’re already informed and will never be as unfit as us?

  • Curlz MT was indeed the best font ever.

  • Jane Dempsey

    I think we’re only seeing a crop of teen actors and fashionistas on social media. I am 25 and through my job, I witnessed 2 hours of teen improv a month ago. Trust me, lots of teens are still awkward.

    • Haley Nahman

      HAHA. Would love to see that

    • pamb

      Was it like the SNL sketch? (I love that sketch).

  • Ingrid Hanna

    Lizzie McGuire, butterfly clips and crimped hair 4EVER!!! I’m pretty grateful for my insanely long awkward phase. These cool kids can wear their chokers and dress like they were born in the 90s, but they will never know the pure bliss of jumping around to B*Witched and sitting in an inflatable chair full of neon colored feathers.

  • kduck

    I’m 25, my niece is 14, and all of her friends intimidate me. I think it’s just a new skill this generation has developed. They’re chameleons, always adapting because of their constant access to what’s cool at this very moment. It’s just part of their environment, they grew up with it, not needing to dissect the process to implement it. It’s just fluid for them.

    Also, body glitter. I used to wear that ish on my FACE.

    • Haley Nahman

      omg glitter on the face!!!

    • Sam

      Ngl part of me misses body glitter so thank goodness Topshop sells it ?

  • Christine Russo

    I went to a Porches concert alone, and found myself gawking at all of the unbelievably cool teenagers around me. The coolest part was that they RARELY touched their phones and were completely lost in the concert, which is ironic because shouldn’t THEY be the ones who are addicted to their phones and feel the need to snap every moment? If I go to a concert with a mostly millennial audience, everyone is snapping, or not even paying attention because they’re texting/scrolling (I even saw a guy on a fantasy football app once). I NEED ANSWERS!!!!! THEY ARE SOOOO COOOL!!!!

  • Brittany

    They are probably peaking. Which I do not envy.

  • kevynryan

    Girl. Preach. As a 29 year old trying to express myself on the vast sea of narcissism that is YouTube, I am quickly humbled by the success, coolness, and non-awkwardness of teenagers online. Like, me at 17? My eyebrows don’t remember that time period because I cruelly all but removed them from my face at that time in some obsessive effort to FIX them. My young fashion icons were the Olsen twins, who seemingly in a matter of a week went from wearing their hair in crisp points secured by butterfly clips and kimono tops to literally being the same age as DVF. I still wonder where these kids’ Cher Horowitz-worshipping stage went. How do they know so much? What the EFF is an Instagram theme? I’m lost.

  • Dymond Moore

    God ,I remember my awkward days. Suspenders, blonde highlights and what felt like the most awkward coming out of all times. To be honest, I still get irrationally jealous of some of the 8th and 9th graders around my town. I mean I’m a senior now, I should’ve made it good by now, right? It’s frustrating especially because I know sometimes (at least in my town) money factors into it, which I don’t necessarily have a lot of. So it’s a lot to chew on some days.

  • Olivia La Roche

    I was terrified of teenagers before I was one, when I was one, and I’m still waiting to shake the phobia…

  • Dawn Davenport

    Having grown up in New York in the early Eighties, this particular breed of teenager existed then and was already well established. They were everywhere, but particularly the Upper East Side. You can see it reflected in many films set there: Manhattan, Rich Kids, The World of Henry Orient,… I could go on. It is not a new phenomenon. They have always existed.

    • Haley Nahman

      I need to see all films about cool new york teens ASAP

  • Hannah

    If I can make a quick analogy…Body/face glitter is to contouring as Lizzie Mcguire is to Kylie Jenner. Amiright ladies?

    • Haley Nahman

      You may and you did and I liked it

      • Hannah

        : )

  • I feel like the older woman in All About Eve when I stalk Gigi and Bella Hadid …except that I was never the starlet

    • pamb

      Except Bette Davis never stalked Anne Baxter. It was Baxter (the younger woman) trying to supplant Davis (the older, more sophisticated one). Not sure that was the movie you were thinking of…

      • I guess I was talking about the first part of movie about feeling like an old hag has-been…there are other movies that use this trope of course but they escape me…any suggestions? Clouds of Sils Maria also popped into my head

  • pamb

    I have a 14 year old daughter. She is nothing like the teen celebs you’ve named, because she is not a celeb. For the most part, their FB/Insta/Snapchats are curated. Was that picture of Lily-Rose Depp taken at home, just hanging out? No. It was at a fashion show or other media event. I think you are giving them too much credit.

    Real teens are just as awkward as they always were, you just don’t see those pics on their feed.

  • Samantha s

    As a 27 year old in the thick of adult puberty I have looked at said teen Instagram perfection in an intrigued but also exhausted way….like, this is fascinating and I want to have some enlightened deep thoughts about them but I’m too busy going to work, meal prepping, folding laundry, drinking beer and listening to podcasts to go there and “give them ten years” and they’ll be doing the same hard, boring stuff I am! (Wednesday night ramble)

  • Beatrice

    Just watched the sex and the city episode “hot child in the city” and I thought of this post the ENTIRE episode. Teenage Kat Dennings vs. Samantha Jones!!!

  • Sam


    • Sam

      All caps for emphasis. My awkward phase lasted well into my twenties. I’m 29 now (for two weeks already eek) and I feel like I’m beginning to get it together

  • now I know I’m not the only adult who idolizes teenagers for their cool confidence. Basically the moment Lorde a.k.a. Ella came on the scene and brought her modern rocker gothic style A game I was in awe. She is the teenager I have always dreamt of becoming!

  • Charlotte Fassler

    1. HI GUYS!
    2. This article sums up all my insecurities
    3. So does this meme:

  • kellymcd

    John Mulaney has this wonderful bit in his New In Town standup special (on Netflix, if your interested) on teenagers and their ability to make him feel insecure and intimidated. I remember watching that and thinking THANK THE LORD I AM NOT ALONE. It may have been for comedy’s sake, but what on earth is going on with these teenagers nowadays that they are so incredibly confident???!!! I couldn’t make legit eye contact with anyone without going red in the face when I was 17. Why is life so cruel?

  • Alyssa G

    Such an interesting piece! As a current 17-year-old, I can definitely attest to the fact that my awkward phase was shortened by my exposure to the Internet.

    xx Alyssa

  • Jenna

    Each generation of teenagers is always more sophisticated, in some way, than the next. My generation might not have been “cool” in the way in which today’s teenagers are but by the time we were out of school, even just high school, we were raring to go. No being “friends” with our parents and hanging with them. Most of our parents couldn’t afford anything we wanted. So we were more independent – we couldn’t wait to get out into the world and be adults, going to school, paying for our apartments and living with multiple roommates if we had to.

    It’s one thing to act mature, but it’s a whole different thing to really be an adult completely on your own, doing your own thing. I actually feel bad for kids today. They don’t have the freedom kids had in the ”90s and before. Being yourself without some (anti)social media to nag you with bullying and criticism.

    Just my opinion, of course.

  • Kimberly Szekely

    Nah, teenagers are definitely cooler now. They are well versed, cultured, and put together. Mind you we aren’t all like that… i think it could possibly be the internet. We are all connected and they seem to just become really awesome. I went to high school with two such people. One is an entrepreneur and the other is a high fashion model. They are younger than me (I’m 19) and completely put together.

  • Kate

    I feel really sorry for younger millennials and Gen z-ers because they didn’t get the chance to grow up without social media. Instead it runs through their lives and sometimes confusingly even seems like it IS their lives, and they will never feel external to it, not completely. I’m Gen Y but Facebook wasn’t a thing until after I had graduated from college. Thank GOD. The other sad thing about the internet is that there’s no sense of specialness. The internet killed cool. I feel the loss of cool’s secrets. Now cool is just branding and product placement and sponsored content. Well I’m being a bit dramatic. Man Repeller is pretty cool. But there is a palpable loss! Does anyone know what I mean?

  • Katerina Bal

    Ok, who remembers “As Told By Ginger” on Nickelodeon? Used to love that show! Ginger with her friends was the ultimate awkward cool I would take any day of the week.