What I Learned Rewatching Gossip Girl in My 20s: A Fresh Perspective on Drama, Fashion and Life Lessons
Okay Rakstars, Gossip Girl (the original) seasons 1 – 6 is on Netflix and I know that your teenage self is dying… a whiff of nostalgia is floating down through your veins. How you wanted to be like the characters, dress in haute couture and just immerse yourself in the Upper East side living with the privileged upper class.
Rewatching Gossip Girl as an adult or adult-ish is like reliving all your teenage dreams – something so familiar yet completely different since well, maybe dreams don’t come true. If you are anything like me, you were obsessed with the scandalous lives of Manhattan’s elite, but your 20-something self? She sees things a little differently. From life lessons wrapped in designer clothing to the importance of personal growth, here’s what I learnt from rewatching Gossip Girl in my 20s.
1. Fashion or Personal Style?
Remember when headbands were the accessory? Buying every single colour and design to match with any outfit. Well, we can certainly thank Blair Waldorf for that. This was her signature look which made us all want to add a little preppy accessory to our wardrobes. Rewatching the show, I realized that while fashion trends come and go (remember silly bandz – omg!), your personal style is there forever. Blair was never afraid to be who she was even when she was figuring it all out. Her dedication to her polished aesthetic, made me realize that true style isn’t about following trends, but about choosing your fashion pieces based on what makes you feel confident. Whether it’s a long beautiful golden dress (like Serena’s cotillion dress) or a gothic look (like Jenny) or a classic Chanel bag or a pair of Louboutin heels, investing in timeless pieces is always a good idea when it resonates with you.
Blair’s Headbands
Serena’s Cotillion Dress
2. Friendship or Frenemies? (Serena vs Blair)
Frenemies became a known concept thanks to Gossip Girl. Friendships are complicated and sometimes even more than a romantic relationship. The most famous relationship throughout the 6 seasons was the bond between Blair and Serena. The on-again, off-again friendship between Blair and Serena showed how people grow, outgrow and repair their relationship. Through thick and thin – challenges arise no matter what. Blair and Serena are a reminder that even sister relationships can change but only true friends learn to forgive through the storm. Rewatching the series in my 20s, I learnt that friendships can evolve and that’s okay.
Blair vs Serena
Blair and Serena's Showdown at Yale
3. Love is not a Fairytale
Blair Waldorf and Chuck Bass
Blair Waldorf and Dan Humphrey
Serena van der Woodsen and Dan Humphrey
Nate Archibald and Jenny Humphrey
Nate Archibald and Serena van der Woodsen
Dan Humphrey and Vanessa Abrams
Blair Waldorf and Louis Grimaldi
Lily van der Woodsen and Rufus Humphrey
Lily van der Woodsen and Bart Bass
Eleanor Waldorf and Cyrus Rose
Jack Bass and Blair Waldorf (??)
Ivy Dickens and Rufus Humphrey
Ivy Dickens and William van der Woodsen
Lola Rhodes and Nate Archibald
Where there any more relationships? Probably so. But lost count.
Watching all these relationships unfold as a teenager, it was easy to be drawn in towards the drama, love and the romanticized mystery. The intensity and passion of young love. But now, re-watching it all, we see the red flags!!. Serena and Nate’s cousin (we could see it coming a mile away). Gossip Girl shows us that love is not a fairytale—it’s messy, complicated and often, it’s about finding yourself before you can truly be with someone else. Enter Chuck and Blair’s relationship, growth is key and that love should lift you up, not tear you down. Rewatching Gossip Girl, I learnt what to look for and what NOT to look for in a relationship. Maybe steer away from complicated rich guys??
Who is your favourite Power Couple? Blair Edition
Blair and Chuck
Blair and Dan
Who is your favourite Power Couple? Serena Edition
Serena and Dan
Serena and Nate
4. Gossip Girl is not a fable
We all believe that we are good people who do not spread rumours or engage in gossip but I mean Susanna in Cubicle C had the inside scoop on Amy’s bridal shower and let’s just say Amy is not a boring accountant. The real world – the rumour mill in offices, school and social life is just as active. See all the celebrity gossip websites – we love to hear the tea. Whether it’s good or bad – we live for the spills. What I learnt is that we must protect our peace – we can get caught up in what other people think which can ruin our mental health but at the end of the day – happiness should be based on your opinion of yourself and not what other people think. When you are true to yourself and don’t compare yourself to others – you can live more zen. Hate comments and other people’s opinions do not really matter so long as you are happy with yourself. Rakstars, don’t let anyone dim your light. Shine bright and be kind always.
Gossip Girl Pilot Voiceovers
5. Upper East Side Riches Doesn’t Equal Happiness
Watching the lives of Manhattan’s elite, we all wanted to be rich like them. Living in penthouses and suites and being chauffeured in black car service. Who can say no to that? I certainly won’t. But what we don’t realize is that none of their lives are hunky-dory. For you see, it’s clear that money can’t buy happiness or in this case love between any of the main characters or that their careers are just as panicky as the rest of us. Sure, they are 10 steps ahead of the ladder – but for them to prove themselves is just as difficult as the rest of us. Serena is on a constant search for self-worth. She is branded as the It Girl where things just come to her which makes her less respectable. On the other hand, Chuck has constant battles with his inner demons – wanting to make a name on his own turf while battling what’s right and wrong. Blair and Nate – well – they are figuring out that true happiness comes from within and not what society’s expectations are or dare I say, trust fund. Dan and Jenny – in order to be like the rich – they had to lose much more of themselves than they wanted.
Chuck Bass and his Inner Demons
Serena’s Grandmother CeCe's Will
6. Finding Yourself is an Ongoing Journey
Rewatching Gossip Girl (okay so maybe like binge watching Gossip Girl seasons 1-6 non-stop) showed me significant character growth. In the past, we had to wait for each episode once a week and when the season ended we waited months and months for the new season. Binge watching is a whole new learning experience. Every character was on a path of finding out who they are. Blair was on a quest to figure out herself away from her relationship with Chuck. Dan had a constant battle with himself as an outsider trying to assimilate himself into the wealth culture hence his book name Inside. I never really understood this watching it the first time around cause I never really experienced it myself. But now that I’m older and certainly hopefully wiser I can see that even in your 20s you are still figuring yourself out and you don’t know the answer right away. It’s okay. The path is never straight and it should be something that we should embrace, not fast forward.
Dan's Tell-All Book - Inside
7. Success and Ambition is a Double-Edged Sword
We want to be successful. Yes we do. But it’s not always positive feedback we get. Blair has a constant drive to succeed, be the best and her ambition is out of this world. She always fights to get what she wants but sometimes it leads her to make choices that are questionable where she would rather sacrifice her relationships with others and create more drama. Her desire to get into Yale, led her down the wrong path with one of her teachers, moreover, the amount of times she and Serena fought. Lesson learned here – have ambition but make sure to strike a balance between what is acceptable and not lose yourself in the process.
Blair Gets Waitlisted at Yale
Growing Up with Gossip Girl
Gossip Girl was definitely a nostalgic trip down memory lane. Flip phones, anyone! Ah, technology! But reminiscing the simple times, the messages it shared offered a new perspective of life, love and personal growth. It was a great series.
So the next time you binge-watch Gossip Girl, remember: you’re no longer just an outsider looking in—you’re someone who’s lived a little, loved a little and learned a lot.
XOXO
Gossip Girl
(Always wanted to do that!)
Love, The Rakstar
