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Gossip Girl Had Me Romanticizing My Life Before I Even Had One

Spotted: me, once again, rewatching Gossip Girl like I don’t already know every scandal, every bad decision, every relationship and every fabulous outfit.

At this point, Gossip Girl is not even just a show I watch.

It’s fall.

It’s nostalgia.

It’s comfort.

It’s a little dopamine hit when I want to watch pretty people wear pretty clothes in pretty places while making absolutely terrible life decisions.

And I eat it up every single time.

But my love for Gossip Girl actually started way before Blair Waldorf was on my television screen wearing a headband.

It started at the library.

My mom used to take us to the library when I was younger, and I LOVED going. I could get lost in there. I was one of those girls who could find an entire world inside of a book and be perfectly content there.

That’s where I found the Gossip Girl books by Cecily von Ziegesar.

Baby.

I was HOOKED.

And looking back now, I think part of what fascinated me so much was that I was reading about a world that looked absolutely nothing like mine.

Money. Manhattan. Designer clothes. Private schools. Socialites. Galas. Apartments that looked like hotels. Jewelry. Parties. Families with money money. The type of stuff I didn’t even know existed yet.

I didn’t know anything about a gala.

I didn’t know what these people were doing half the time. 😂

But I was reading about it.

And that’s something I don’t think we talk about enough when it comes to reading and even television.

Sometimes seeing another world expands your imagination for your own.

It doesn’t mean I wanted to literally become these characters.

Absolutely not. These people were a mess.

But it showed me that life could be bigger than what I could physically see around me at the time.

And then the show came out.

And Baby… They Brought My Books to Life

I had already built this world in my head from reading the books, so actually SEEING the Upper East Side on television?

The fashion?

The jewelry?

The hotels?

The apartments?

The galas?

The brunches?

The flowers?

The drama???

Oh, baby.

You couldn’t tell me anything.

There was something about Gossip Girl that made luxury feel like part of the actual storytelling.

It wasn’t just, “Look, these people are rich.”

The environments mattered.

Blair’s bedroom mattered.

Lily’s apartment mattered.

The Palace mattered.

The Met steps mattered.

The dresses mattered.

The jewelry mattered.

Even them sitting around eating breakfast before school looked fabulous as ever.

And for a girly girl like me?

COME ON.

That show was feeding me.

It gave me this peek into glamour before I even had language for the things I liked.

And I think that’s one reason I still love beautiful things today.

Jewelry. Details. Presentation. Creating an atmosphere. Romanticizing ordinary things. Making your home feel good. Putting yourself together just because.

Luxury doesn’t always have to mean buying the most expensive thing in the room.

Sometimes luxury starts with developing an eye for what makes life feel beautiful to you.

And Gossip Girl definitely helped develop mine.

Now Let’s Talk About My Girl Blair

Everybody on that show has their pros and their cons.

And Blair Waldorf had enough cons to fill up Bergdorf’s.

I DON’T CARE.

That’s my girl. 😂

Was she mean?

Absolutely.

Controlling?

Girl.

Scheming?

Professionally.

Could she be insecure, jealous, elitist and completely out of pocket?

YES.

But Blair was also ambitious as ever.

She cared about tradition. She loved beautiful things. She wanted a beautiful life. She was intelligent. She was strategic. She loved HARD. She had standards. She could fall completely apart, cry her eyes out, put on a headband and somehow be plotting again by lunch.

There was something very feminine about Blair without femininity meaning weak.

And I loved that.

She wasn’t trying to be the cool girl who didn’t care.

Blair cared about EVERYTHING.

Her future.

Her relationships.

Her clothes.

Her reputation.

Her friendships.

Her table settings probably.

That girl cared.

And honestly?

I respect it.

And Then There Was Chuck Bass…

Listen.

I KNOW.

😂😂😂

Watching Chuck and Blair as an adult is a completely different experience than watching them when I was younger.

There were moments when they were toxic as ever. Moments when both of them needed to leave each other alone. Moments where I’m watching now like, “Girl… stand UP.”

But I would be lying through my teeth if I said I didn’t love watching their story.

Because I did.

Still do.

Their chemistry was ridiculous.

The longing?

The games?

The fashion?

The dramatic declarations?

Chuck standing somewhere in a three piece suit looking emotionally constipated?

Blair acting like she couldn’t stand him while clearly being obsessed with that man?

Cinema.

I said what I said.

But the older I get, the more I see Chuck outside of just Chuck and Blair.

Chuck had MONEY money.

Hotels. Drivers. Private jets. Tailored suits. Connections. Power. Access to basically anything he wanted.

And none of that could fix what was going on inside of him.

That part hits differently when you’re older.

Chuck spent so much of his life dealing with his relationship with his father and trying to figure out what being a Bass actually meant.

Bart was definitely not giving warm and fuzzy father of the year.

Chuck grew up surrounded by money and privilege, but emotionally there was a lot missing.

And you could see that in the man Chuck became.

He built this entire identity around being untouchable.

“I’m Chuck Bass.”

That wasn’t just a funny little line after a while.

That was his armor.

Chuck Bass doesn’t need anybody.

Chuck Bass has money.

Chuck Bass has power.

Chuck Bass gets what he wants.

Chuck Bass doesn’t have to explain himself.

Except underneath all of that?

Chuck desperately wanted to be loved.

And baby, THAT man did not know what to do with those feelings.

😂

He could negotiate a business deal easier than he could tell somebody what was actually happening inside of him.

And I think a huge part of Chuck’s story was him trying to figure out whether being Bart Bass’s son meant he was automatically destined to become Bart Bass.

Chuck wanted his father’s approval while also resenting him.

He wanted to prove himself to Bart.

Then he wanted to prove he didn’t need Bart.

Then he wanted to build something of his own.

And that is a complicated relationship to have with a parent.

Because sometimes you can spend so much time trying NOT to become somebody that they are still controlling who you become.

And Chuck had to figure that out.

Now understanding Chuck’s childhood does not magically make every decision he made okay.

Absolutely not.

There were times when Chuck was WRONG.

Period.

But understanding where somebody’s behavior comes from and excusing their behavior are two completely different things.

And the older I get, the more interested I am in that part of his character.

Because Chuck had to learn that power was not the same thing as emotional strength.

Control was not the same thing as security.

Money was not the same thing as love.

And shutting everybody out did not actually make him untouchable.

If anything, it made him lonely.

And then there was Blair.

Blair was one of the few people who could see straight through all that “I’m Chuck Bass” foolishness.

She saw the arrogance.

She saw the darkness.

She saw the ambition.

But she also saw the person underneath all of it.

And Chuck saw Blair’s ugly parts right back.

That’s probably part of why their relationship had such a hold on me.

They weren’t falling in love with perfect versions of each other.

They knew each other could be difficult.

They knew each other could be selfish.

They knew each other could be manipulative.

They knew each other could be completely ridiculous.

They saw each other.

Was it always healthy?

Absolutely not.

Was I still watching?

Absolutely yes.

😂

And I think that’s one of the things that makes Chuck more interesting to me as I get older.

His story wasn’t really just about becoming successful.

He was born into success.

His story was about becoming his own man.

Because you can inherit somebody’s money.

You can inherit their last name.

You can inherit their expectations.

You can even inherit some of their wounds.

But eventually, you have to decide what you’re going to carry forward and what ends with you.

And Chuck spent a lot of Gossip Girl trying to figure that out.

Also…

He was a Taurus.

And as a fellow Taurus?

I’m just saying.

The stubbornness.

The luxury.

The loyalty when he finally decided somebody was HIS person.

The expensive taste.

The hardheadedness.

The need to build something tangible.

The man basically said, “I have emotional problems, so naturally I need another hotel.”

😂

Very Taurus.

I saw you, Chuck.

But underneath the suits, money, schemes, women, hotels and the famous last name was somebody trying to answer a question that actually wasn’t very different from everybody else on the show:

Who am I when I stop letting the people who came before me decide who I’m supposed to become?

And THAT is the Chuck Bass storyline I appreciate much more now that I’m older.

Serena Was That Girl Too

I actually like Serena.

She had that effortless thing Blair sometimes hated her for.

Serena could walk into a room looking like she just woke up, throw on something sparkly, shake that blonde hair around and somehow everybody’s boyfriend, husband, cousin and doorman was suddenly in love with her.

Annoying?

Probably.

Iconic?

Unfortunately, yes.

But underneath all of that, Serena’s story was actually pretty sad sometimes.

She spent so much time running.

Running from mistakes.

Running from who she used to be.

Running toward men.

Running away from men.

Running back to another man.

Girl was TIRED.

And watching her now, I notice that more.

She wanted to reinvent herself so badly, but she kept dragging pieces of her old life into the new one.

There is definitely a lesson in that.

You cannot create a new version of yourself while constantly letting old chaos decide who you are.

Dan… You Had Me Fooled, Sir

Dan was our outsider.

And that was important because we needed somebody looking into that world from the outside.

He judged them.

He wanted to be nothing like them.

He thought their world was shallow.

Meanwhile…

Sir.

You wanted IN.

BAD.

😂

And that’s what makes Dan interesting to me now.

Sometimes we criticize the things we secretly want access to.

Sometimes the person standing outside the gate talking the most mess is also studying exactly how to get through it.

Dan was watching everybody.

Learning everybody.

Writing everybody.

And eventually becoming part of the exact world he claimed to hate.

Do with that what you will.

Nate Was Gorgeous… But Sir, Please 😂

Now Nate?

Nate was cool or whatever.

And obviously, the man was GORGEOUS.

Let’s get that out of the way first.

Beautiful face. Beautiful hair. Walking around the Upper East Side looking like somebody personally sculpted him for a Ralph Lauren campaign.

We get it.

😂

But Nate also annoyed me.

Because Nate had this habit of judging everybody else for how they moved.

He could be very critical of Blair, Chuck, Serena, his family and basically anybody who made decisions he didn’t agree with.

And sometimes I would be watching like:

Sir… you do realize you live here too, right?

That was one thing about Nate that frustrated me.

He wanted to play fair in a world that was not fair.

And wanting to have morals is obviously not a bad thing.

But sometimes Nate acted like everybody had the same choices available to them.

They didn’t.

Everybody was dealing with different families, different expectations, different pressures, different secrets and different consequences.

Sometimes people were surviving situations Nate didn’t completely understand.

And instead of trying to understand why somebody made a certain decision, he could jump straight into judging the decision.

That bothered me.

Because it’s very easy to tell somebody else how they should play the game when you aren’t the one holding their cards.

And Nate had his own family drama too.

His father.

His grandfather.

Money.

His family name.

The expectations placed on him.

Trying to separate himself from the Archibald legacy while still benefiting from being an Archibald.

There was actually a LOT there.

But what made Nate interesting and frustrating at the same time was that he eventually started becoming versions of the very people he criticized.

And THAT is where I would be looking at him sideways.

Because Nate could make himself the martyr sometimes.

Everybody else was playing dirty.

Everybody else was manipulating.

Everybody else cared too much about money, status, power or connections.

Meanwhile, give Nate enough seasons and suddenly he’s making questionable decisions too.

Sir.

Welcome to the Upper East Side.

😂

That’s why I think Nate could be immature sometimes.

He wanted everything to exist in these very clean categories of right and wrong until life put him in a position where doing the completely “right” thing wasn’t so simple anymore.

And honestly, that is probably one of the more realistic parts of his character.

It’s easy to criticize somebody’s choices when you’ve never had to make them.

Then life puts you in your own complicated situation and suddenly you understand why everybody wasn’t playing by the little rulebook you created in your head.

Nate eventually had to learn that too.

So no, I didn’t dislike Nate completely.

He had his moments.

He had a heart.

And once again…

The man was FINE.

We cannot erase history.

😂

But the judgmental, self righteous, martyr side of Nate?

Yeah.

I could have done without that.

Especially when he kept becoming pieces of the very world he spent so much time criticizing.

And maybe that was Nate’s real lesson.

Be careful judging how somebody survives an unfair world. Life has a funny way of eventually putting you in a position where you finally understand why the choices weren’t as simple as they looked from the outside.

Jenny Humphrey Wanted More, And I Get It

Now Jenny is interesting to me because Jenny was another character standing on the outside looking in.

Except unlike Dan, Jenny wasn’t about to sit there pretending she didn’t want it.

Baby girl wanted IN.

She wanted the clothes.

She wanted the status.

She wanted the parties.

She wanted to belong.

She wanted to create.

She wanted to be somebody.

And honestly, I understand that part of her character.

Jenny was ambitious.

She was talented.

She could sew her tail off.

She had an eye for fashion.

And she was a young girl looking at this glamorous world around her thinking, “Why can’t I have some of that too?”

That part is human.

Where Jenny started losing herself was when wanting more became more important than remembering who she was.

And whew.

There’s a lesson right there.

Wanting more for yourself is not the problem. Losing yourself trying to prove that you deserve more is.

Jenny kept changing herself to survive whatever room she was trying to enter.

And the higher she climbed socially, the more complicated everything became.

That’s what makes her storyline kind of sad to me now.

Because underneath all of that rebellion was a young girl trying to figure herself out in an environment where everybody was constantly telling her what she needed to have, wear, know or become in order to matter.

She wanted transformation.

And sometimes transformation will have you trying on versions of yourself that don’t actually fit.

I can appreciate Jenny much more when I look at her that way.

But girl…

Some of those decisions?

A MESS.

Lily Rhodes Van Der Woodsen Bass Humphrey Whatever Her Name Was That Season 😂

Okay.

Now THIS is a character I appreciate so much more as I’ve gotten older.

I have a real soft spot for Lily.

When I was younger, Lily was just Serena’s rich, fabulous mother.

Now?

I see the woman.

I see the mother.

I see the daughter.

I see somebody who spent a lot of her life trying to convince herself that she was nothing like her own mother while sometimes repeating the same patterns she hated.

And THAT is real.

Lily grew up with expectations.

Appearances mattered.

Family reputation mattered.

Money mattered.

Who you married mattered.

How the family looked from the outside mattered.

So Lily learned how to keep everything beautiful on the surface even when everything underneath was falling apart.

And then she became a mother.

A flawed one.

A loving one.

A frustrating one.

A mother dealing with children who had their own pain and struggles, including Eric’s suicide attempt and Serena being constantly misunderstood while also misunderstanding Lily.

That changes the way I watch her now.

Because Lily did not always get it right.

AT ALL.

Sometimes I’m still looking at the television like, “Lily, girl, what in the world are you doing?”

😂

But I understand her more.

She was trying to protect her children while still carrying all of the things she had learned from her own upbringing.

Sometimes she protected the image when she should have protected the person.

Sometimes she thought money or connections could fix something that actually needed honesty.

Sometimes she made decisions for her children instead of listening to them.

And sometimes she really did show up.

That’s parenthood.

You can love your children more than anything in this world and still have your own flaws.

You’re still learning.

You’re still carrying your own experiences.

You’re still trying to figure out which parts of the way you were raised you want to keep and which parts need to end with you.

Becoming somebody’s mother doesn’t magically erase everything that happened before you became one.

Lily showed that.

And I appreciate that about her character now.

I also appreciate her relationship with Serena differently.

Because Serena spent so much time feeling misunderstood by Lily while Lily herself had spent a lifetime feeling misunderstood.

They were more alike than either one of them probably wanted to admit.

And underneath all their arguing and dysfunction, I always felt like Lily genuinely loved her children.

She just didn’t always know how to love them without also trying to control the outcome.

And baby…

That is a whole conversation by itself.

And Since We’re Talking About Lily… THE FASHION

Excuse me.

Lily was serving.

EVERY SINGLE TIME.

Everybody talks about Blair and Serena when we talk about Gossip Girl fashion, as we should.

But Lily?

Grown woman elegance.

The coats.

The jewelry.

The bags.

The hair.

The dresses.

The way she could walk into the room looking like she owned the building and probably knew the person who actually did.

Lily’s fashion was grown woman luxury.

She didn’t have to scream.

She didn’t have to chase trends.

She just looked expensive.

And the jewelry?

Baby.

You already know I was looking.

Lily helped make the adult side of the Gossip Girl world just as visually interesting as the younger characters.

She was proof that femininity, glamour and personal style do not disappear when you become somebody’s mother.

If anything, Lily said move over little girls.

Mama has arrived.

And Then Here Comes Georgina Sparks…

Now we CANNOT talk about Gossip Girl without talking about Georgina Sparks.

Because whenever Georgina appeared?

Baby, whatever peace these people thought they had was OVER.

😂

Georgina did not come on that show to sip tea and mind her business.

She came to CLOCK IN.

And I loved it.

She was chaotic. Manipulative. Smart. Completely unpredictable. And somehow always knew exactly which little secret to pull out when everybody was getting too comfortable.

Georgina was one of those characters where the second she popped up on the screen, you already knew something was about to happen.

And that is exactly what a show like Gossip Girl needed.

She was not pretending to be innocent.

She was not trying to convince us she was the nice girl.

Georgina knew she was Georgina.

And there was something hilarious about that.

Everybody else would be trying to maintain their reputation while Georgina would basically walk into the room like:

“So which one of your lives are we ruining today?”

Girl. 😂

But underneath all of the chaos, Georgina was also incredibly observant.

She knew people.

She knew their weaknesses.

She knew what they were hiding.

She understood that the Upper East Side was full of people pretending everything was perfect when almost everybody had something they did not want exposed.

And Georgina?

She would expose it.

QUICKLY.

She was like the human version of Gossip Girl sometimes.

She watched.

She collected information.

And she knew information was power.

That doesn’t mean I would want Georgina anywhere near my actual life.

Absolutely not.

Keep that woman several blocks away from my household.

😂

But as a CHARACTER?

Give me Georgina every time.

Because sometimes a show needs somebody who walks into the room and completely flips the table over.

And Georgina Sparks understood the assignment.

The Older I Get, the More I Understand Everybody

That’s probably the biggest reason Gossip Girl never gets old for me.

My perspective keeps changing.

When you’re young, you watch it for the drama.

Then you watch it for the relationships.

Then the fashion.

Then you start noticing the parents.

Then the friendships.

Then the class differences.

Then ambition.

Then identity.

Then motherhood.

Then family patterns.

Then you start realizing almost everybody on that show was trying to answer the same question:

Who am I when everybody else already has an opinion about who I’m supposed to be?

And THAT part aged beautifully.

Blair was trying to become powerful enough to never feel second best.

Serena was trying to prove she could become someone different from her past.

Dan wanted access while pretending access didn’t matter.

Nate was trying to figure out who he was without his family deciding for him.

Jenny wanted transformation so badly that she had to learn what could happen when you start losing yourself inside of it.

Chuck had to figure out whether he was doomed to become the worst parts of the man who raised him.

Lily was trying to be a different woman and mother than the one she grew up watching while discovering that breaking family patterns is a lot more complicated than simply saying, “I’m not going to be like my mother.”

And Georgina?

Georgina was going to be Georgina whether anybody liked it or not.

Everybody was becoming.

Everybody was messing up.

Everybody wanted love.

Everybody wanted status.

Everybody wanted to belong somewhere.

And then Georgina wanted to know everybody’s business.

Very glamorous.

Very human.

Very messy.

Maybe That’s Why I Keep Coming Back

Gossip Girl gave teenage me escapism.

It gave me imagination.

It gave me fashion.

It gave me characters I could love, hate, defend and scream at.

It introduced me to a world I hadn’t experienced yet.

And maybe that’s what I appreciate most now.

Before I had certain experiences, books allowed me to imagine them.

Before I knew exactly what my taste was, stories helped me discover it.

Before I knew anything about galas, beautiful tables, Manhattan penthouses, designer fashion or Upper East Side drama, there I was at the library checking out my little Gossip Girl book and entering another world.

That’s actually kind of beautiful when I think about it.

A library card can take a little girl somewhere her circumstances haven’t taken her yet.

And sometimes seeing more makes you imagine more.

Not because you need Blair’s life.

Not because you need Serena’s wardrobe.

Not because you need Lily’s penthouse.

And definitely not because you need Chuck Bass’s relationship problems.

But because you’re allowed to look at the world and say:

Oh. There’s more out there.

And then decide what your version of more looks like.

So yes, every fall, I’m probably going to find myself right back on the Upper East Side.

Cozy in my house.

Watching rich people ruin their lives in gorgeous outfits.

Judging everybody like I wasn’t rooting for the same foolishness last year.

And loving every single minute of it.

Some shows you watch once.

Some shows become part of your personal history.

Gossip Girl is that for me.

And apparently, I’ll be defending Blair Waldorf, appreciating Lily’s fabulous self more every year, waiting for Georgina Sparks to come wreck somebody’s perfectly planned evening and still not seeing it for Vanessa until I’m 85.

Sorry, girl.

XOXO,

Shayskiij

Note2Self: Sometimes the first glimpse of the life you want comes through a story. Keep reading. Keep watching. Keep imagining. And then go create a version that’s actually yours.