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1. Twilight (2008)

When Twilight premiered in 2008, it became an instant sensation and sparked a cultural obsession with supernatural romance. However, while it left an undeniable mark on pop culture, this film has some major underlying issues.

Once viewed as swoon-worthy, Bella and Edward's relationship feels problematic in hindsight. He was controlling, exhibited stalker-like behavior, and gaslit her into believing that she imagined his supernatural abilities.

Add in the fact that Edward is technically over a century old when Bella is a high schooler, and it's clear why Twilight might not resonate with audiences the same way in 2025.

2. Knocked Up (2007)

Directed by Judd Apatow, Knocked Up was initially well-received despite heavily leaning on outdated gender stereotypes. The movie follows responsible and career-driven Alison, who is forced to navigate an unplanned pregnancy with slacker Ben.

Even though Knocked Up delivers plenty of laughs, it also portrays women, especially Alison, as rigid and joyless. Katherine Heigl, the lead actress, criticized this, too, saying the film "Paints the women as shrews, as humorless and uptight, and it paints the men as lovable, goofy, fun-loving guys."

3. Norbit (2007)

This movie might've showcased Eddie Murphy's ability to transform into multiple characters, yet Norbit is still more cringeworthy than comedic. The portrayal of Rasputia, an over-the-top and domineering woman whose character is built around fat-shaming jokes, is particularly offensive.

Moreover, Murphy also plays Mr. Wong, a wildly stereotypical caricature of an elderly Chinese man.

4. Shallow Hal (2001)

Shallow Hal may have set out to deliver a message about inner beauty, but it really missed the mark. Again, this film relies on fatphobic humor, with Gwyneth Paltrow's character serving as the target of the jokes.

It arguably reinforces stereotypes about weight and attractiveness, and Gwyneth (who wore a fat suit) actually called the movie a "disaster" in 2020.

5. White Chicks (2004)

Featuring over-the-top humor and absurd disguises, White Chicks was a hit in 2004. Nonetheless, it's a tired portrayal of women as materialistic, shallow, and obsessed with their looks.

The premise involves two FBI agents posing as socialites during a Hamptons weekend, and it was always meant to be ridiculous. Even so, there are certain scenes that are especially questionable, like when an athlete at the club attempts to spike a woman's drink.

6. Brüno (2009)

Brüno was intended to be a bold satire, Sacha Baron Cohen's specialty, but it crosses the line of edgy humor. He plays an exaggerated, flamboyant Austrian fashion journalist, and the mockumentary was meant to expose homophobia.

Despite that, the movie incorporated a lot of outdated gay stereotypes and might've reinforced the notions as opposed to challenging them. In fact, Gay and Lesbian Alliance Against Defamation (GLAAD) representative Rashad Robinson called the work "problematic in many places and outright offensive in others."

7. Wedding Crashers (2005)

Wedding Crashers revolves around two men who lie their way into weddings to manipulate women into sleeping with them. At its core, the film's plot is unsettling and questionable.

Aside from that, it features gay stereotypes, a racist grandmother, and scenes that blur the lines of consent. All that being said, t's obvious why this movie wouldn't fly today.

8. The Notebook (2003)

The Notebook is still one of the most favored romance movies of all time, so this may be an unpopular opinion, but some of its most iconic moments are more disturbing than anything.

There's no denying that Noah and Allie's love story is passionate, but his relentless pursuit of her is borderline manipulative. Remember when he threatened to let go of the Ferris wheel if she didn't go on a date with him?

Plus, once they actually get together, their relationship is filled with constant fighting, including scenes when Allie hits Noah. Female-on-male violence has traditionally been glossed over in films, but today, Hollywood is moving away from these problematic depictions.

9. How to Lose a Guy in 10 Days (2003)

This movie follows advice columnist Andie Anderson, played by Kate Hudson, who wants to write an attention-grabbing piece. She finds Ben Berry, an advertising executive who's arguably creepy and manipulative.

While How to Lose a Guy in 10 Days may be a classic rom-com, it relies on gender stereotypes that can feel more offensive than humorous now.

10. Mean Girls (2004)

Finally, we can't forget about Mean Girls, one of the most iconic teen comedies of the 2000s. Sure, it's filled with endlessly quotable lines and a sharp take on high school cliques, but it also has relentless body-shaming.

Many of the scenes would hit differently in today's more body-positive era, making Mean Girls a more cringey watch in 2025.

Blake Lively (Serena van der Woodsen)

Of all the Gossip Girl cast alumni, Blake Lively is arguably the most well-known. Not only has she gone on to major roles in movies — including The Age of Adaline, The Shallows, All I See Is You, and most recently, It Ends with Us— but she's also married to fellow actor Ryan Reynolds (married in 2012).

Blake shares four beautiful daughters, James, Inez, Betty, and the youngest (born in 2023) whose name has not been announced publicly with Ryan. True to her Gossip Girl character, she's quite the fashionista! In her spare time, she likes to hang out with her BFFs, who just so happen to include Taylor Swiftandthe Sisterhood of the Traveling Pants ladies.

Leighton Meester (Blair Waldorf)

Leighton Meester has a career that would make even her cunningly ambitious Queen B character proud. Since Gossip Girl's end in 2012, she's acted in films including Life Partners, The Judge, The Weekend Away, and most recently, EXmas. She even recorded and released songs such as "Good Girls Go Bad" with Cobra Starship and the solo effort "Somebody to Love," and even starred on Broadway in Of Mice and Men back in 2014.

Leighton is married to actor Adam Brody (The O.C., Jennifer's Body, Gilmore Girls) as of 2014. She has two kids – one daughter and one son.

She has been heavily involved in philanthropy while taking on acting projects, primarily volunteering and campaigning with Feeding America and the Los Angeles Food Bank.

Taylor Momsen (Jenny Humphrey)

Long gone are the days when Taylor Momsen played Dan Humphrey's sweet (and a bit messed up) little sis, Jenny. The actress left the Gossip Girl cast in 2010 in order to pursue her dreams of a music career, and all these years later, she's still doing just that as the frontwoman of the uber-successful rock group, The Pretty Reckless. With four records under their belt, the four-member band has supported bands like Evanescence, Soundgarden, and Guns N' Roses, and has toured in numerous cities and music festivals.

Momsen has typically kept her dating life on the down-low. She is currently single and appears to be putting all of her energy into her band.

Penn Badgley (Dan Humphrey)

Everyone’s favorite Gossip Girl — er, guy — Penn Badgley, followed in his on-screen sister's footsteps after the show ended, pursuing his musical interests with rock band MOTHXR. The band's most current project, Centerfold, was released back in 2016.

Badgley has since acted in several movies and TV shows including Easy A, The Paper Store, and Here Today, but his most notable work has been on the ongoing book-based Netflix series, You. He plays Joe Goldberg, a charming bookkeeper with eerily odd characteristics, especially when it comes to love.

Badgley currently has a podcast titled Podcrushed, which explores the awkwardness of adolescence and revisits guests' best (and worst) middle school memories. He cohosts with Nava Kavelin and Sophie Ansari. One episode even features ex-Gossip Girl co-star, Leighton Meester!

Badgley is married to singer and doula Domino Kirke as of 2017. Kirke already had a child from a previous relationship. Badgley and Kirke had their first son together in 2020.

Ed Westwick (Chuck Bass)

Ed Westwick tapped into his angsty side post-Gossip Girl, starring as Tybalt in a 2013 adaptation of Romeo & Juliet. Since then, he has fought crime as Kent Grainger on Wicked City, played a crime lord on Snatch, and sold double-glazed windows on White Gold. Is there any role he can't play? Most recently, Westwick stars in the movie DarkGame.

With a background in music, Westwick also currently sings in the bandFor You. Their most recent release is the song "Tailspin," and they're set to release a new single "Here Comes Trouble" in March 2024.

Westwick had been dating model and actress Amy Jacksonsince 2021, with the pair getting happily engaged during a ski trip in January 2024.

Chace Crawford (Nate Archibald)

Following his stint as a wealthy Upper East Sider on Gossip Girl, Texas native Chace Crawford tried his hand at playing a greedy oil worker on ABC's short-lived TV series, Blood & Oil. He's had several film roles since – you can catch him in movies like Undrafted, Eloise, Nighthawks, even voice-actingin Belle. Most recently, Crawford stars as The Deep on The Boys.

Crawford has previously dated Carrie Underwood, Rachelle Goulding, and Rebecca Rittenhouse, though he is currently single as a Pringle.

Jessica Szohr (Vanessa Abrams)

Jessica Szohr, who played Dan Humphrey's BFF slash on-again, off-again girlfriend (needless to say, we were confused too), has been a lot busier than her character was after season four, when she was all but written off the show.

In the years since Gossip Girl, the actress scored several roles on TV shows such as Complications, Kingdom, Twin Peaks and The Orville. She even starred in Taylor Swift's music video for "22" back in 2013!

Jessica also welcomed a daughter with her longtime boyfriend in early 2021.

Jessica currently hosts a podcast called "XOXO" that dives deep into the Gossip Girl cast, crew, and behind-the-scenes moments. Some notable episodes have featured Zuzanna Szadkowski (Dorota), Aaron Tveit (Tripp van der Bilt), Kelly Rutherford (Lily van der Woodsen), and Michelle Trachtenburg (Georgina Sparks).

Michelle Trachtenberg (Georgina Sparks)

Since her stint as the "bad girl" Georgina Sparks, Michelle Trachtenberg landed roles on shows like Criminal Minds, NCIS: Los Angeles, Sleepy Hollow, and Sister Cities among other numerous series and movies. She even reprised her role as Georgina for the 2021 remake of Gossip Girl on HBO Max!

She managed to keep her personal life largely out of the tabloids, including her dating life. The last update on her relationship status was in 2023, and that she was dating her talent agent, Jay Cohen. She reportedly previously dated Shawn Ashmore, Joshua Radin, and Jason Segel.

Unfortunately, Michelle passed away on February 26, 2025.

Kelly Rutherford (Lily van der Woodsen)

Besides being a New York Fashion Week icon (we'd expect nothing less of Lily van der Woodsen's alter ego!), Kelly Rutherford has popped up in several TV shows over the years, including Quantico, Jane the Virgin, and Dynasty.

She also frequently travels to France and Monaco, where, after years of custody battles with her second ex-husband, Daniel Giersch, she has extensive visitation rights to see her two children, who reside there with their father.

"Yes, it was a challenging time. It was a heartbreaking time," she told People. "But I focus on the good most of the time, I really do," she says. "I'm very thankful of where we are. I have a great relationship with my kids."

When she's not with her kids or working on a project, Kelly is dropping iconic 'fit pics on her Instagram account.

Matthew Settle (Rufus Humphrey)

Matthew Settle, who played rockstar dad Rufus Humphrey, continued acting after the Gossip Girl cast dissolved. He hasn't been on any other TV shows other than one episode of Criminal Minds: Beyond Borders in 2016. He mostly stuck to movies, acting in titles like Ouija, Marshall the Miracle Dog, and Valentine: The Dark Avenger.

Settle is also a dad of two children, having welcomed his first with actress and model Naama Nativ in 2009. He had divorced her in 2011 and went on to have a second baby with girlfriend Maria Alfonsin in 2015.

Zuzanna Szadkowski (Dorota Kishlovsky)

Though Blair's loyal maid and, ultimately, best friend, wasn't technically a main character, there's no denying that it would have been a different show without her unwavering presence! Zuzanna Szadowski has dabbled in film and television since then, appearing in shows such as Girls,The Good Wife, and Modern Love.

In 2010, she partnered with Sam Weisman to open The Sam Weisman Studio, an acting school (now closed).

Oh, and did we mention she just so happens to be one of Leighton Meester's real-life BFFs?

1. Wearing Green (And Pinching Those Who Aren't)

One of the easiest ways to cash in on the luck of St. Patrick's Day is by wearing green. This hue has deep ties to Ireland, which is often called the "Emerald Isle" due to its lush, rolling landscapes. Beyond its natural beauty, green also carries historical significance and symbolizes Irish nationalism and cultural pride.

The best part? There's a mischievous side to this fun and festive tradition. More specifically, those who forget to wear the color might find themselves on the receiving end of a pinch.

This playful custom is more common in the U.S. than in Ireland and stems from the idea that wearing green makes you invisible to leprechauns, who are known for their trickster ways. So, to avoid being "spotted" (or pinched), make sure you add a splash of green to your outfit.

2. Drowning A Shamrock In Whiskey

In Ireland, a well-known tradition is "drowning the shamrock," and it's believed to bring good luck. The shamrock has long been linked with Irish heritage and fortune. It's said to have been used by St. Patrick to explain the concept of the Holy Trinity.

So, on March 17, many celebrate by dropping a fresh shamrock into a glass of whiskey, drinking the beverage, and then tossing the shamrock over their left shoulder for good luck.

3. Doing An Irish Jig

Get into the spirit of the holiday by learning an Irish jig! This energetic dance is a staple of Irish celebrations and is often performed in parades or festivals. It features quick footwork, pointed toes, and rhythmic hopping.

The Irish jig has deep roots in Celtic culture, possibly evolving from ancient clan marching tunes or early Celtic circle dances. Traditionally, Celts danced clockwise for joyous occasions and counterclockwise for mourning.

You can take a dance class, join in at a local event, or just work on some jig steps at home!

4. Searching For Four-Leaf Clovers

Hunting for a four-leaf clover is a classic St. Patty's Day pastime, and if you manage to find one, you should consider yourself super lucky.

While shamrocks typically have three leaves, the rare four-leaf clover is actually a genetic mutation, making it a real symbol of good fortune. In fact, experts estimate that only one in every 10,000 clovers has four leaves!

Test your luck this holiday by scanning a patch of clover quickly. Our brains are surprisingly good at spotting irregular patterns.

5. Release The "Devil" From Your Irish Soda Bread

Did you know that cutting a cross on top of Irish soda bread isn't just for aesthetics? According to Irish folklore, scoring a cross into the dough "lets the devil out" and ensures good luck and protection for your household.

This superstition, rooted in both Christian and pagan beliefs, was thought to ward off evil spirits. It also serves a practical purpose by allowing steam to escape, thus helping the bread bake evenly.

6. Run In A St. Patrick's Day Dash

Running a race might not be the first thing that comes to mind for March 17, but it's become a really fun tradition. St. Patrick's Day dashes can range from quick 5Ks to half marathons, with plenty of family-friendly walks for those who prefer a more leisurely pace.

Participants dress up in green, wear shamrocks, and sometimes even race while sporting leprechaun hats! It's a great way to stay active and possibly run your way into some good luck.

7. Chow Down On Corned Beef And Cabbage

It's just not St. Patrick's Day without a plate of corned beef and cabbage. Even though many associated this dish with Ireland, it actually has Irish-American roots.

When Irish immigrants arrived in the U.S., they found corned beef to be a more affordable alternative to traditional bacon. Paired with cabbage, potatoes, and carrots, it became a comforting and flavorful meal that stuck as a holiday staple.

8. Kiss Someone Who Is Irish

Finally, you've definitely seen the phrase "Kiss me, I'm Irish" on T-shirts before. This fun saying is tied to the tradition of kissing the Blarney Stone in Ireland, an act that's said to bring good luck.

However, not all of us have the ability to visit the Blarney Stone. So, kissing an Irish person is another way to honor the custom in the spirit of good fortune.