The Exhausting Pursuit of Being Cool & Pretending Not to Care

Alternative Title: I've never been a natural, all I do is try try try

Hi friends! This week's episode dove into something that's been on my mind forever- the exhausting pursuit of being "cool" and how it shapes our self-image. Sam and I had an incredibly honest conversation about our own experiences with trying to fit in, the pressures we faced, and how social media has created an entirely new dimension to this struggle.

In the full episode, you'll hear the story of how I dated someone in high school just to try to become popular (spoiler it didn’t work and then I dragged him down in popularity HA!) and pretended to LOVE sports for years (until sobriety forced me to admit I couldn't sit through a baseball game without drinking).

Below are the highlights from the episode, but there's so much more in the full version. If you've ever struggled with feeling "not cool enough", or wondering how its all connected to the patriarchy, you’ll want to listen to the full episode.

The Cool Girl Chronicles: Our Personal Confessions

Here’s a confession… I was OBSESSED with being cool growing up. Embarrassingly, desperately obsessed.

I moved around a lot as a kid, which meant I was constantly trying to fit in with new groups. I'll never forget moving to New York in seventh grade, confidently wearing what I thought was my coolest outfit—jeans with lavender sparkles and a faux fur cuff at the bottom. I walked into school and immediately got hit with "What on God's earth are you wearing?"

I was mortified. From that moment, I became desperate to fit in—to wear the right clothes, know the right people. I would have literally sold my soul to be popular. (Which worked out quite well- there’s nothing that makes you more popular than desperately wanting to right?)

Sam had a completely different experience. She accepted early on that she wasn't going to be part of the cool crowd and found her own way. She shared: "I never touched the cool stratosphere. I never got there, but I had enough friends that I just knew I wasn't and I accepted that."

I unfortunately couldn’t find a photo of this outfit so this photo of limited too will have to suffice

When "Cool" Never Ends: Social Media's Generational Game

Remember when "being cool" was just a high school and college thing? As Sam put it in our conversation,

"There used to be a time and place for popularity in high school. Women older than me would tell me, 'Don't worry, it gets better. You'll get to a point where you don't care.'"

But that grace period of aging out of coolness has maybe disappeared.

Social media has completely transformed how "cool" works. It's extended the high school cafeteria into our thirties, forties, and beyond. Even worse, it's created this bizarre cross-generational pressure where millennials like us are now being called "cheugy" by Gen Z for wearing skinny jeans while simultaneously feeling pressured to keep up with 20-somethings on platforms we helped build.

What's fascinating is how different generations experience this digital coolness race. Sam and I discussed how Gen Z grew up with cameras constantly documenting their lives, making them hyper aware of being "caught" doing something uncool. They've developed a completely different relationship with authenticity as a result.

Kate Kennedy (a previous podcast guest) made an incredible point on her recent podcast that Sam and I discussed: never before in history have different generations been so exposed to what other generations think is cool.

When I was young, my parents only knew about what was “cool” from me or my friends or observation. Now when we scroll on social media, we're all consuming the same content, you’re forced to watch younger generations say how uncool or weird you are and even make fun of you (to your face). It’s almost creating this weird flattening of generational differences while simultaneously heightening the awareness of them.

It's also creating these strange paradoxes: Gen Z claims to value uniqueness and authenticity more than any generation before, yet there's an incredible conformity in how that "authentic uniqueness" is expressed. Meanwhile, millennials who once pioneered social media are now caught in an awkward middle space—too young to age out of trends but old enough to feel constantly behind them.

(Full disclosure- if you are Gen Z we love you, so please take this with a grain of salt. This is simply 2 millenials sharing their frustrations and observations. We could be very wrong).

The Cool Girl Phenomenon: A Patriarchal Trap

One of the most powerful moments in our conversation came when we discussed the iconic "Cool Girl" monologue from Gone Girl. If you haven't heard it, here's the gist:

The "Cool Girl" is hot but not high-maintenance. She drinks beer but stays thin. She likes sports and never complains. She's essentially a male fantasy wrapped in female form—a woman who has erased her own preferences to become what men want.

As we discussed in the episode, this isn't just about women policing other women. The "cool girl" standard ultimately stems from patriarchal expectations. That's why the impossible double standards exist:

• Be casual enough to drink beer and eat pizza, but stay a size two

• Be low-maintenance, but always look perfect

• Have opinions, but only the right ones

• Be sexy, but not for yourself—for the male gaze

It's exhausting. And it's why both Sam and I have found freedom in abandoning that pursuit.

Finding Freedom Beyond "Cool"

The most liberating realization? Cool is an ever-moving target that no one can actually hit.

Sam put it perfectly: "We're just desperately chasing this ability to feel accepted and have a community that accepts us. But then the trends come and go because the trends don't change the root problem."

Every season brings new trends—barrel jeans, then skinny jeans, then back to wide-leg. Get fillers, now dissolve your fillers. Be curvy, now be thin. It's exhausting, and ultimately, it's not sustainable. Read below for our take on SkinnyTok.

I shared how I finally abandoned this pursuit when I got sober. I couldn't pretend to enjoy things I genuinely disliked anymore. I couldn't fake-love sports or force myself to watch sports games sober. Recovery forced me to embrace who I actually was. Not who I thought others wanted me to be.

Is SkinnyTok Just Pro-Ana Content in Wellness Packaging?

Journal Prompts to Explore Your Relationship with "Cool"

If you find yourself still chasing an elusive definition of "cool," here are some questions to consider:

1. When was the first time you remember trying to be "cool"? What triggered it?

2. What authentic parts of yourself have you downplayed to fit in?

3. If you could design your own definition of "cool" based solely on what you value, what would it include?

4. What would change in your life if you stopped trying to meet external standards of coolness?

5. Can you identify one way you're still chasing "cool" today? How might you release that pressure?

What We Didn't Have Time to Cover Here

There's so much more we explored in the full episode that I couldn't fit into this post:

• Our deep dive into the original "Cool Girl" monologue from Gone Girl and how it perfectly captures what many women have experienced in relationships

• The surprising fourth wave of feminism that's emerging as more women reject these impossible standards entirely

• Why Gen Z missed out on "club culture" and how that's shaped their relationship with authenticity and spontaneity

• Our embarrassingly honest confessions about the most cringe-worthy things we did trying to be cool

Listen to the Full Episode!

If any part of this resonated with you, definitely listen to the full convo. Sam and I go MUCH deeper into how these pressures have shaped us, where they come from, and most importantly - how to finally break free from them.

The most liberating part of getting older is that you see how ridiculous the game of being cool is and you can consciously choose to stop playing.

What "cool girl" standards have you abandoned? What parts of yourself have you reclaimed? I'd love to hear your stories in the comments!

With love and zero desire to be cool anymore,

Amanda