Not So Chic with Elli Freeman

Apparently, the reason I need 47 verbal affirmations that someone still likes me isn't because I'm a hopeless romantic. It's my attachment style. How chic!

This week, we're unpacking the four attachment styles, why some of us chase people who pull away, why emotional availability can feel suspiciously boring, and the deeply humbling realization that sometimes we're the ones making dating complicated.

I'm also putting my own attachment issues under a microscope, because nothing says personal growth quite like realizing you've been conducting psychological experiments on men who didn't consent to participate.

Consider this your introduction to attachment theory, with a side of self-awareness, questionable dating habits, and a few uncomfortable truths.

Xoxo, Elli

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I have trust issues. With men, friendships, my own decisions, and quite frankly, the universe's ability to follow a schedule.

This week on Not So Chic, we're discussing the deeply inconvenient reality that life does not come with a detailed itinerary, a return policy, or a customer service representative.

From being the girl who was never quite in the group chat to convincing myself a man was my future husband when he couldn't even commit to dinner plans, I'm unpacking how disappointment, rejection, and a few questionable characters have turned me into someone who is constantly waiting for the other shoe to drop.

We're talking about the difference between anxiety and intuition, why we confuse control with security, how past friendships affect new ones, and why trusting yourself doesn't actually mean making the right decision every time. Oh, and the rather devastating realization that sometimes the lesson isn't learning how to make someone love you. It's learning when to leave.

Plus, in Guest Therapy, we're discussing the emotional hostage situation that is waiting to see if your ex texts you happy birthday.

Because maybe trusting the process isn't about believing everything will work out. Maybe it's about knowing you'll be okay even when it doesn't.

Love you, mean it. xx

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I have spent an embarrassing amount of my life trying to become the kind of woman who walks into a room and commands attention. Meanwhile, I’m 23 years old, still occasionally forget how to operate my limbs in public, and somehow had more confidence at 13 with a mouth full of braces. Explain that one.

This week, we're talking confidence. Not the kind that requires perfect hair, a fabulous body, or the approval of every man within a five-mile radius. The kind that comes from actually liking yourself, even when nobody else is around to validate it.

We're discussing why 13-year-old me was absolutely convinced she was the cat's meow at her barn mitzvah, how to stop treating other people's opinions like performance reviews, and why putting on a sexy thong and dancing to Beyoncé alone in your kitchen might be a legitimate form of personal development.

Plus, an Uber driver with questionable intentions, the art of being particular without being an asshole, and some big-sister advice on finding a therapist when you don't know where to start.

Confidence may be an inside job, but fabulous underwear certainly helps.

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Have you ever seen an Instagram Story of people hanging out without you and suddenly decided you have no friends, everyone secretly hates you, and you should probably move to a new city? Same!

This week, we’re talking about being left out: the group chats you’re not in, the dinners you weren’t invited to, and the deeply humbling experience of zooming into the reflection of a martini glass to figure out who else was there. I’m also telling the story of the time my friends made an entirely new version of our group chat without me—and I was so delusional I searched my phone because I thought I had accidentally muted it. Spoiler: I had not.

We’re getting into why being left out hurts so fucking badly, the difference between actually being excluded and your friends simply having lives that unfortunately do not revolve around you, and why sometimes you don’t even want to go—you just want the ceremonial invitation. LET ME reject YOU.

Plus, in Guest Therapy: Hinge pen pals, men who will happily plan your hypothetical wedding but cannot plan drinks for Thursday, and why 72 hours of nonstop texting does not, in fact, make him your future husband.

If you’ve ever conducted a psychological autopsy over an Instagram Story, this one’s for you.

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I've spent approximately 23 years being my own biggest hater, and I fear it's time for a rebrand.

This week, we're talking about self-compassion, otherwise known as treating yourself with the same kindness you extend to literally everyone else. From accidentally dropping my baby cousin at nine years old to waking up half-naked with McDonald's chicken nuggets in my cleavage, we're unpacking the difference between holding yourself accountable and putting yourself on trial for every mistake you've ever made.

I'm also reading a letter I wrote to myself at 19 during one of the hardest periods of my life, revisiting the little girl who desperately wanted to fit in, and discussing why you don't have to hate yourself into becoming a better person.

Because you can regret your decisions without regretting who you are. And frankly, life is hard enough without living with a bully who knows all your insecurities.

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Apparently, you don't need a boyfriend to go through a breakup. Who knew?

This week, we're discussing the seven stages of heartbreak, the particular psychological warfare of ending a situationship, and the deeply humbling experience of grieving a future that existed entirely in your head. From convincing yourself that an Instagram story view means he's coming back to drafting your seventeenth final text, we're getting into all of it.

I'm sharing what I've learned about choosing yourself when it's the last thing you want to do, why closure might be a scam, and how to move forward when you're not quite ready to move on.

Because sometimes the hardest person to get over is the one you never actually dated.

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For most of my life, I thought everyone was counting their shampoo pumps, strategically positioning their bedroom door, Googling every bodily sensation and occasionally convincing themselves that if something wasn’t just right, they might die in their sleep.

Apparently, we were not all doing that.

This week, we’re talking about OCD: the intrusive thoughts, compulsions, reassurance seeking, rumination and desperate pursuit of certainty that I didn’t even realize were running my life until I was 19. I’m sharing some of my strangest childhood rituals, the moment I finally understood my own brain, what ERP taught me, and the deeply annoying phrase that changed everything: maybe, maybe not.

Because recovery isn’t learning how to guarantee that nothing bad will happen. It’s learning that you don’t need the guarantee.

Plus, Guest Therapy tackles the post-grad panic of not knowing what the hell you’re doing with your life—and why maybe you don’t need all your ducks in a row. You just need to know which duck you’re dealing with today.

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Being single is not a problem I’m currently trying to solve.

This week, we’re talking about how to actually enjoy being single without swearing off love, pretending you never get lonely, or treating every man you meet like a potential husband. From awful Hinge dates and imaginary perfect boyfriends to protecting your friendships, romanticizing your own life, and realizing that being chosen was never really the goal.

Maybe I’ll fall madly in love one day. I hope I do. But I’m not spending the years before that happens waiting for my life to start.

He can join when he gets here. We’ll get him a wine glass too.

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Shame is the voice that turns “I embarrassed myself” into “I’m embarrassing,” “they didn’t text me back” into “I’m unlovable,” and one slightly questionable social interaction into a seven-year recurring thought before bed.

This week, we’re talking about shame: where it comes from, why it thrives in secrecy, the difference between shame and guilt, perfectionism as shame management, vulnerability hangovers, people-pleasing, body image, and the exhausting experience of constantly imagining yourself through everyone else’s eyes.

I’m also sharing some of my own greatest hits in shame—including accidentally lying to my dentist about my entire life, my complicated relationship with calling myself an influencer, and the occasional decision to say fuck it and choose fun over being perceived perfectly.

Because the goal isn’t to become completely shameless. It’s to stop letting shame decide who you’re allowed to be.

And maybe the things you’ve spent your entire life trying to hide aren’t the things making you unlovable. Maybe they’re just the things making you human.

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I’ve spent most of my life romanticizing everything—relationships, friendships, college, moving to a new city, rainy days, heartbreak… you name it. And while I don’t ever want to stop finding magic in ordinary life, I’m starting to realize there’s a difference between romanticizing your life and becoming attached to a version of it that only exists in your head.

This week, we’re talking about the stories we write for ourselves, why situationships can sometimes hurt more than actual relationships, grieving potential instead of people, and what happens when reality doesn’t follow the script we imagined.

Maybe growing up isn’t about becoming less romantic. Maybe it’s about realizing the best parts of your life might be the ones you never saw coming.

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I’ve referenced the fact that I didn’t go to my high school graduation before, but I’ve never actually told you the full story of why.

My senior year ended with an anonymous Instagram account, a “worst friend” superlative, hundreds of my classmates watching the whole thing unfold, a meeting with my principal, my parents pulling me out of school, and ultimately, me not walking at graduation.

And somehow, six baby bunnies also almost get burned alive in the middle of all of this. You genuinely cannot make this shit up.

But underneath the absolutely unhinged high school story is something I still think about years later: how easy it is to forget there’s an actual human being on the other side of a screen. We’re talking cyberbullying, teenage cruelty, mental health, the way schools handle—or don’t handle—these situations, and why you will never regret being kinder than necessary.

Grab your blanket and sweet treat. This one is a STORY.

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Grief is one of those things I’ve always been scared to talk about because there’s no perfect way to put it into words. But after losing my grandfather almost two years ago, I’ve realized just how little we actually talk about what it feels like to lose someone you love.

In this episode, I’m opening up about my own experiences with loss, being with my Papa during his final moments, and everything grief has taught me since. I talk about the guilt, loneliness, and strange little moments no one prepares you for—like watching the rest of the world keep moving when yours feels like it has completely stopped.

Most of all, I’ve learned that grief isn’t something we simply “get over.” It changes shape. Everyone can lose the same person and still be grieving an entirely different relationship, and no one else gets to decide how big of a piece that person occupied in your heart.

This is an episode about loss, but more than anything, it’s about love—and how lucky we are to have people worth missing forever.

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The internet has never been more powerful—or more confusing. Every day we're bombarded with advice, opinions, AI-generated content, perfectly curated lives, and an endless stream of people telling us how to think, look, work, eat, and live.

In this episode, I'm unpacking my complicated relationship with social media, why comparison has become an impossible game to win, why I believe digital literacy is just as important as financial literacy, and why the thing that scares me most isn't artificial intelligence—it's losing our ability to think for ourselves.

Because the question isn't whether technology is good or bad.

It's whether we can stay human while living alongside it.

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I spent years thinking I was behind. Behind on dating, behind on sex, behind on experience. So I tried to become the kind of girl who could do casual hookups without catching feelings… and completely lost myself in the process. Today we're talking about hookup culture, why so many of us confuse validation with intimacy, and the biggest lesson I've learned: there is nothing chic about abandoning yourself just to fit in. Plus, one of the most humiliating hookup stories of my life, Chic of the Week, Not So Chic, and Guest Therapy.

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This week we're talking about one of the most unserious—and strangely revealing—parts of modern dating: the ick.

From men chasing ping pong balls to wearing Band-Aids, we've all experienced those completely irrational moments where attraction disappears in an instant. But what if the ick isn't always about them? What if sometimes it's about what closeness, kindness, or emotional availability brings up in us?

In this episode, I'm unpacking the difference between an ick and a red flag, why I seem to get the ick from genuinely nice guys, how chasing can feel safer than receiving love, and why we so often mistake anxiety for chemistry. We talk about attachment, self-sabotage, wanting vs. needing in relationships, and how to tell the difference between intuition, discernment, and fear.

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Comparison has a way of making us feel like everyone else is ahead. In today's episode, we're talking about why we compare ourselves, the difference between comparison and jealousy, how to genuinely celebrate other people's success, and why your timeline was never meant to look like anyone else's.

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Apparently being a big sister became my entire personality. This week we're talking about siblings, the people who become siblings, why I spent 23 years trying to save my little sister, and what happens when the caretaker finally learns to let go. Plus, Guest Therapy for anyone convinced they're behind in life.

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For years I thought confidence came from fitting in. Dressing like everyone else. Dating the "right" people. Chasing validation from strangers, boys, and anyone willing to tell me I was enough.

Turns out I couldn't have been more wrong.

In this episode, I'm talking about the biggest shift I've made over the last few years: learning how to live a life that's actually aligned with my values instead of everyone else's expectations. From outpatient therapy and value sorting to dressing for myself, dating authentically, and finally letting my inner child have a seat at the table, this is a conversation about what happens when you stop shrinking yourself just to belong.

If you've ever felt like you're constantly performing a version of yourself that everyone else seems to like more than the real you, I hope this episode reminds you that the people who are meant for you will never require you to abandon yourself.

Because the goal was never to fit in.

It was to finally feel like yourself.

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I've been called an "old soul" for as long as I can remember, but for years it felt less like a compliment and more like a reminder that I never quite fit in.

In this episode, I'm talking about what it was like growing up feeling different—being the kid who wanted tea at The Peninsula, spent recess in knitting club, obsessed over interior design before most people cared about decorating their bedrooms, and always seemed a few steps ahead emotionally. I share how being deeply observant shaped my friendships, dating life, career, and mental health, and why I spent so many years wishing I could just be like everyone else.

We talk about loneliness, sensitivity, overthinking, finding your people, and the moment I finally stopped trying to outrun the parts of myself that made me different. Because while being an old soul can feel isolating, it can also be one of the greatest gifts you'll ever receive.

If you've ever felt out of sync with the people around you, this one's for you.

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Body image isn't always self-hatred. Sometimes it's just constantly being aware of your body.

In this episode, I share my experience with body image from ballet classes and dieting in middle school to gaining weight in college, losing it after graduation, and learning how to stop fighting myself every day. We talk about comparison, food noise, body neutrality, and why taking care of your body feels very different than trying to punish it.

This isn't an episode about weight loss. It's an episode about making peace with yourself.

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