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Why Your Late 20s Feel Like Adolescence All Over Again

May 30, 2017

When I was a young teenage kitten, I fantasized about entering the seemingly illustrious decade of my 20s — the decade that would be the great escape from the endless pangs of teenage angst that consumed my teen-girl soul.

Like most naive teenage girls who grew up drugged by an excess of “Sex And The City,” I believed that by the time I reached my late 20s, I would have my sh*t gorgeously together.

I was going to be a thriving Carrie Bradshaw, only younger and even fiercer.

I visualized myself living in the West Village of Manhattan in a fabulous apartment with exposed brick and white walls smattered with impossibly cool modern art.

My future would have an endless stream of adoring, doting lovers, all of whom were obsessed with me. Id consume petal pink cocktails in sophisticated martini glasses in the chic company of fashion editors and artists. Id sign a book deal, in Manolo Blahnik shoes, with perfectly blow-dried hair.

I was confident that by 27, I would have found the person I was going to spend the rest of my life with, have an exciting career in the arts and feel secure and confident in my physical appearance.

But here I am, kittens — 29-years-old, and I couldn’t feel further away from my 16-year-old girl fantasy. I feel more lost than I ever have. Most days, I feel like a shy, confused 13-year-old girl dressed up in adult clothes.

I’m self-aware enough to know I have a lot to be grateful for: I’m healthy (unless I’ve fallen ill with a cheap champagne hangover). I have a vast array of fascinating, crazy, magnificent friends that I adore with every fiber of my 29-year-old being. I might not be making a Manolo Blahnik worthy paycheck, but I do get to wake up every morning and march into a job that I love.

But this article isn’t about the material possessions. Because let’s face it, some people in their late 20s are making bank, and some of us are still praying our credit cards don’t decline every time we swipe them at the corner deli.

I’m talking about something that cuts deeper than money, a feeling that no living, breathing entity in their late 20s is immune from: restlessness.

If you were to scratch beneath the surface of career success and money, you’d discover that every 26- to- 29-year-old youknow feels restless. This was supposed to be the time we had life figured out, yet we feel more lost and confused than we did in our teens and early 20s.

The best way I can describe it is, well, exactly like adolescence (only more intense, because you have bills to pay).

It’s the awkward in-between phase.

In your early 20s, you’re a no-holds-barred wild child.

It’s cute to be the party girl. There is no shame in vomiting out the window of a taxi at 4 am. It’s funny, not embarrassing, to be holding your stilettos in your hand as you stumble home from the club, barefoot at an ungodly hour. Sleeping in your makeup has little consequence.

Sometime around the age of 26 to 27, though, being a hot mess is no longer hot. Sh*t just isn’t cute anymore.

But most of us in our late 20s are hardly ready for full blast adulthood, either. We aren’t quite ready for children, marriage or all of that “real grown-up” stuff.

Being in your late 20s is like being in a bizarre purgatory; you’re no longer comfortable being the 21-year-old blacking out at the party, but you’re also not totally comfortable in a power suit and sensible shoes.

It’s just like being 12 all over again, when you feel too old to be deemed a kid but not yet ready to do teenage things.


Sh*t gets real.

The great expanse of your future lies beautifully ahead of you, so in your early 20s, you have nothing to lose.

Marriage is a million miles away, so it’s totally okay to have a wildly liberating one-night stand or date the toxic musician you would never dream of building a life with.

The moment I hit 27, though, sh*t just started to feel frighteningly REAL. Because the closer you creep to 30, the more you begin to realize real life is actually starting to happen.

You watch your friends get engaged, one-by-one. And then another one gets pregnant. And then another one becomes CEO of a major company.

All of a sudden, you realize the person you’ve been hooking up is nothing more than a warm body, and you start to crave depth. You start to realize the choices you’re making are going to directly affect your future.

Its scary.


You worry you’re not where you should be.

I remember being 11-years-old and terrified to go to summer camp because I was convinced I was the only girl who had gotten her period. I felt like I was an overdeveloped freak of nature and spent the summer hiding tampons in my pillowcase, praying for a miracle. Maybe it just wouldn’t come ever again.

On the other hand, my best friend, Pippa, had daily panic attacks about getting changed in the locker room for the gym class. She was as flat as a board and was terrified to change in front of the full-chested popular girls. She stuffed her bra with tissue and dreamt of having boobs every single night (now she’s a 34 DDD).

The aforementioned scenarios are the perfect metaphor for the end of your 20s.

If you’re single, you fear you’re going to be a crumbling spinster with 30 adult cats for the rest of your life. If you’re engaged, you fear that youre missing out on the party, that maybe you’re tying the knot too soon.

You constantly compare yourself to peers and freak the f*ck out over living too young or too old of a life.

Its a specific kind of hell, reminiscent of seventh grade.


You question your identity.

When I was a kid, I was a free bird who ran around the backyard climbing trees and collecting bugs. I was a wild-haired, free spirit who never questioned myself.

Until I turned 13 — and suddenly, being scrappy and muddy wasn’t cool anymore. Being a tomboy put me in an unattractive category.

So I changed myself to fit in. I started wearing tight jeans and Steve Madden platforms. But I wasnt comfortable in my skin. I didn’t recognize myself in the mirror, and I questioned every move I made.

When I was in my early 20s, just like when I was a kid, I knew exactly who I was. I was an aspiring actress by day and a shot girl by night who lived with her older brother in West Hollywood. I was fully confident and secure in what I was doing.

And then, I turned 26. The endless rejection from the industry and pressures to look a certain way began to take a toll on my soul. I began to question if I even wanted to be an actress anymore.

Suddenly, I was that lost 13-year-old again, uncertain of who I wanted to be and what I was going to do with my life.


Nothing is what you expected.

Often, the things you poured your soul into during your early 20s don’t pan out the way you expected.

You suddenly realize you don’t want to spend the rest of your life pursuing what you studied in college. You’re not sure if you want to get married to the guy you’ve been dating for two years — or you’re not sure if you want to get married at all.

The late 20s is a time of great questioning. The fantasy of what your life should be like starts to wear off, and the sting of reality begins to set in.

And while it’s nothing short of terrifying, don’t fret, because you’re actually in a really powerful place.

The fantasy of your early 20s might be quickly fading, but you’re on the brink of entering something even better than a fantasy — you’re about to enter REALITY. And reality will always kick the sh*t out of a delusional dream.

And never forget that we need confusing times of epic questioning in order to discover who we really are.

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Category: rejuvenation