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“The More You Stare, The More You Laugh”: 30 Grammys Looks That Sent The Internet Into A Spiral
With the 68th Grammy Awards just around the corner, the excitement isn’t limited to who will take home the gilded gramophone. For many viewers, the red carpet is just as important, especially when it comes to outfits that push boundaries and leave people talking for years to come.
And if there’s one look that still dominates conversations ahead of this year’s ceremony, it’s Biana Censori’s jaw-dropping appearance at the 2025 Grammys.
Censori arrived with her husband, Kanye West, wearing a large black fur coat. A few moments later, she dropped the coat in front of the cameras, revealing a completely sheer mesh dress underneath.
Apparently, her ensemble had no lining, no coverage, and no attempt to hide anything. The moment quickly took over social media and, for many, overshadowed the night’s actual award winners.
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Image credits: Getty/Jon Kopaloff
Several netizens called it performance art or a visual reference to Ye’s Vulture era; others felt it crossed a line.
“This isn’t fashion,” one social media user wrote, while another said the moment made them uncomfortable.
Despite the backlash, Ye doubled down on X, praising his wife. He called her “smart, talented, brave, and hot.”
“People asked how your mother feels. You don’t know my mama.” He later claimed the stunt helped them “beat the Grammys,” referencing the spike in searches for Censori’s name.
As unsettling as the moment was, it didn’t happen in a vacuum. The Grammys have always been a place where artists take risks with their fashion choices. Over the years, stars like Lady Gaga, Cardi B, Nicki Minaj, Miley Cyrus, Doja Cat, and others have all turned the award function red carpet into a headline-worthy moment.
As the 2026 Grammys approach on February 1, we’re looking back at 30 of the wildest, boldest, and most unforgettable Grammy outfits of all time.
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#1
Cardi B, 2019
Auntriarch 2 days ago
Absolutely. It ticks all boxes except practical. And that's the least of her concerns
Load More Replies... Jaya 2 days ago
Don´t look at those kind of outfits as 'clothes', but as a 'mobile piece of art' or a 'sculpture made out of fabric'. That way you can enjoy them the way they are meant. I like this one, the shapes are awesome, the colour is very pretty. It's not just that pink thing that's great, I also really like the pearl around the pelvis and neck, and the texture on the bodice.
persephone134 2 days ago
There is too much of everything, but it's a lovely colour combination. How does she even walk, let alone go to the toilet?
Charlotte 2 days ago
I imagine there's a way to detach the lower part once the red carpet photos are done
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Andie Day 2 days ago
Well, at least we can say her bits are covered. Agreed, gorgeous color and texture but it's a rather overdone.
Charlotte 2 days ago
Overdone for any other occasion, but for this? Nah, let designers go mad
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#2
Miley Cyrus, 2024
Less than an hour before picking up her first-ever Grammy for Best Pop Solo Performance for Flowers, Cyrus hit the red carpet in a custom Maison Margiela look that immediately got people talking.
The singer wore a sculptural, barely-there gown made entirely of gold safety pins. Inspired by John Galliano’s “Susy Sphinx” collection from 1997, the dress hugged her body in intricate patterns, paired with Margiela Tabi heels.
However, viewers got instantly distracted by her hair, and not in a good way.
Social media quickly zeroed in on the look as a whole, as one wrote, “Look like she stuck her finger in a plug socket and her hair stood on end lol.”
“Hate the hair on her. Aged her big time,” another wrote.
“Please, someone arrest her hairdresser,” a third joked.
Others were less amused, with one saying, “Well, she deserves something, but certainly not this outfit,” while another added, “Don’t like that look on her.”
LakotaWolf (she/her) 2 days ago
I have a friend online who does lovely knit?/crocheted? (sorry, I don't know which one, though I think crochet) flowers that she then connects into gorgeous blankets. I told her I am commissioning her for an absolutely obnoxiously glorious vest in the same connected-flowers style XD I did also find someone's pattern for a crocheted eyeball and told my friend she could make the vest out of connected crocheted eyeballs if she'd prefer...... XD
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persephone134 2 days ago (edited)
Taking boho to extremes. This is a combination of wearing a doily and channeling 1960s' Liz Taylor's Cleopatra look. The hair is also very retro, but I couldn't say which era,
#3
Jennifer Lopez, 2000
persephone134 2 days ago
It caused a stir back in the days. I'm still convinced she wore her morning gown.
LakotaWolf (she/her) 2 days ago
I would like to crumble into dust at the fact that you referred to 2000 as "back in the days" XD
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#4
Rihanna, 2011
AtMostAFabulist 2 days ago (edited)
I like this. She looks fresh. She can definitely pull this look off.
LakotaWolf (she/her) 2 days ago (edited)
She does look rather fresh.. like she's covered in rings of fresh frosting or fresh whipped cream XD EDIT: I should mention that I actually do think it's rather cute and I actually do like it; it just reminds me of whipped cream/frosting XD
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Jenna Kay 2 days ago (edited)
I don't know why, but this dress immediately made me think of Dr. Seuss.
#5
Chappell Roan, 2025
Chappell Roan made sure her Grammy debut wouldn’t be forgotten. Arriving for the first time as a nominee in six major categories, the Pink Pony Club singer stepped onto the 2025 red carpet in a vintage Jean Paul Gaultier couture gown from 2003.
The pale blue and mustard tulle dress featured an Edgar Degas-inspired ballerina print and was decorated with a nest-like arrangement of sticks and blue flowers.
Online reactions were as entertaining as her ensemble. One wrote, “I thought she had lovingly crafted one out of paper.”
Another summed it up perfectly, “It’s bad fashion done very well.”
Others couldn’t unsee the details, with comments like, “Her hair thing looks like shredded mozzarella,” and “I thought she had spaghetti on her head.”
JSL 12 hours ago
Don't insult Cyndi Lauper. Cyndi can pull this off, but not Chappell.
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LakotaWolf (she/her) 2 days ago
Yeah, I don't LIKE like the outfit, but this is kind of her look, as far as I know, isn't it? I don't know much about her.
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Drop Bear from Hell 2 days ago
Is she going to an audition for 'Whatever happened to Baby Jane?'
HamsterGirl 2 days ago
Her extreme makeup always ruins it for me personally. Personally I think shes really pretty without all that makeup on. But then again, that could just be me 🤷♀️🤷♀️
Otto Katz 2 days ago
If her makeup wasn't over the top, the outfit is really good But the makeup ruined it
#6
Britney Spears, 2017
AtMostAFabulist 2 days ago
Her face looks like a 45 yr old woman, who has been waitressing all day.
Andie Day 2 days ago
Well, it's pretty hard to beat this. Looks like it came out of a Goodwill bin.
Load More Replies... #7
Cyndi Lauper, 1984 :
Travelling Stranger 2 days ago
she dressed like she thought her grandma would try to do a young rebellious "fun" woman look
LakotaWolf (she/her) 2 days ago
As soon as I read your comment, I scrolled back up to take a closer look at the headband, and I can STILL feel that fabric texture. Gah!! My mom used to sew things for me made out of that shít and make me wear them all the time in the 80s XD
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#8
Ok Go, 2007
Andie Day 2 days ago
I could actually get behind the suits-fabulous fabric, cut, and fit, you darlings. But take off the stockings. It just looks dumb.
Natalia 2 days ago
You should watch some of their music videos, they're incredible
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Dee Hampton 1 day ago
Fabric reminds me of the wallpaper in an Indian restaurant from the '70s
#9
Doja Cat, 2024
More Information 2 days ago
Her nipples are blurred out because they were clearly visible.
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Lil be lil 17 hours ago
This belongs in the boudoir. And those are definitely not the heels for that rag.
zububonsai 1 day ago
My grandma, in her 90-ies, would 100% use the Saxon phrase "So möcht'ch ni' tot über'm Gartenzaun hängen" (sprich, von allen gesehen werden) = "(looking) this way I don't want be draped across the garden picket fence." = "I don't wanna be found/seen by my neighbours... looking this way.") OR "Damit kannste noch die Kinder erschrecken" ("It's good for making kids scream and run."). // She ticks all the "beauty" boxes, young, slim, symmetrical... but uglifies herself ... I don't get it.
#10
Ceelo Green, 2017
CeeLo Green has never exactly blended into a red carpet, but at the 2017 Grammys, he took things to a whole new level.
Arriving in his then-new musical persona, Gnarly Davidson, the performer stepped out in a full head-to-toe metallic gold outfit that immediately stole the spotlight.
The structured, armor-like look featured exaggerated shoulders, a high collar, and a matching helmet, giving off everything from sci-fi villain to fantasy character energy.
The outfit left social media viewers in splits as one wrote, “Ceelo had a Samsung explode in his face, then turned into an iPhone.”
“CeeLo Green lookin like he just killed all the Power Rangers,” another wrote.
“This guy is trying WAY too hard to be the center of attention,” someone commented bluntly.
Others couldn’t get past the sheer absurdity, with one admitting, “I can’t stop laughing irl, imagine wtf people at the Grammys were thinking.”
Another added, “He also looks 4 feet tall… the more you stare, the more you laugh.”
Zoe Vokes 2 days ago
He is about 5 ft 5 inches tall. People have speculated before about him having dwarfism due to his proportions but apparently he’s just short.
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#11
Charlotte Lawrence, 2024
Andie Day 2 days ago
Agreed. Fits perfectly, lovely cut and fall. The fabric would be beautiful with a black or silver underlay.
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#12
Dencia, 2016
HamsterGirl 2 days ago
If the bra looking shirt was different I'd be all OVER this outfit. The "shirt" kinda ruins it for me tho
#13
Annie Lenox, 1995
Back in 1995, Annie Lennox reminded everyone that the Grammys red carpet doesn’t always have to take itself seriously.
The singer showed up in a black-and-white latex French maid outfit complete with sheer stockings, towering dominatrix boots, and Minnie Mouse ears on top.
Lennox later explained that the look was very much intentional. “What else is a girl going to wear to the Grammys?” she quipped at the time.
"It was an ironic statement on my part — Minnie Mouse is a female cartoon character, partly innocent and partly Disney corporate. It summed up how I felt about the music industry at the time,” she told The Hollywood Reporter.
Looking back, not everyone knew what to make of it as one user questioned, “Annie Lennox baby, what are u doing?”
LakotaWolf (she/her) 2 days ago
I mean... isn't that what the Grammys is these days, a costume party? XD Look at these other entries! XD
Load More Replies... #14
Katy Perry, 2019
Auntriarch 2 days ago
You are too kind, the top is only ok in comparison to the skirt
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#15
Girl Crush, 2017
Shannon Rowley 1 day ago
Serious question: How do many of them sit in the seats? Especially with this outfit.
StumblingThroughLife 1 day ago
By the look of it, she wouldn't be able to sit at all, lol.
Load More Replies... Linda Conaghan 2 days ago
Please tell me they're water balloons you can pull off and throw at people 😄
#16
Toni Braxton, 2001
At the 2001 Grammys, Braxton proved that sometimes less fabric really does more damage. The singer stepped out in a barely-there white halter gown by Richard Tyler.
Her dress featured a plunging neckline, a completely open back, and two sky-high slits that left very little to the imagination.
Braxton later admitted she knew exactly what she was doing, explaining she wanted to go risqué before settling down.
"I decided that before I got married and had babies, I'd wear this,” per US Weekly.
While the moment made history, the internet did not love the execution.
“She is amazing, but what a terrible dress,” one person commented.
Another joked, “I thought she was only wearing long tissue.”
Auntriarch 2 days ago
That strip of ribbon over her hip looks like her nan added it to save her from embarrassment
Charlotte 2 days ago
The fabric also bunches oddly where it attaches at the front
Load More Replies... Stephanie L Thesing 2 days ago
Tbh, if I had her looks and bod, I’d wanna dress like that too ;)
#17
Taylor Swift, 2021
Taylor Swift’s 2021 Grammys look was pure Folklore fantasy. The singer arrived in a custom Oscar de la Renta mini dress covered head to toe in pressed floral appliqués.
Her dress quickly became one of the most talked-about looks of the night, especially after a seam rip appeared under her arm. Swift handled the minor wardrobe malfunction like a pro as she smiled through photos.
She completed her look with a matching face mask, baby pink Christian Louboutin heels, and Cathy Waterman jewelry.
Online users had thoughts with one writing, “If only she had done a photo shoot in a field with this thing.”
Others saw home décor potential instead, joking, “Hear me out… pillows,” followed by, “Like couch pillows or decorative pillows,” and, “Tbh I think it would make beautiful pillows.”
LakotaWolf (she/her) 2 days ago
Weirdly, I feel like if the dress was just a smidge longer, it'd look amazing. I'm not speaking from a "gasp, a woman showing her ankles!" perspective, but from a fashion perspective. Because the "edge" of the dress is uneven due to the differing length and shapes of the flowers' petals, it looks a bit strangely cut off at the thigh. I think if it was knee-length it'd be stunning.
Jaya 2 days ago (edited)
I actually feel like it should be a little bit shorter, like real minidress length. I'm afraid that making it knee-length might push it into grandma territory, like it needs the sexiness of the shortness to keep it young and cool. I don't know, if it was knee-length I just envision the "quirky older aunts" wearing it. I might be wrong though.
Load More Replies... Charlotte 2 days ago
But somehow not with this dress. This dress says sandals or bare feet to me
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#18
Blac Chyna, 2023
LakotaWolf (she/her) 2 days ago
Okay, friend. That's it, that's the best comment I'll see all day. I laughed out loud XD
Load More Replies... Charlotte 2 days ago
It's a lot - and then just legs. I think a top and head dress like that needs acres of trailing black skirt or it's just unbalanced
#19
Tierra Whack, 2019
AtMostAFabulist 2 days ago
I like the jacket, not the dress. It would have made more impact if she wore a solid color dress.
#20
Noah Cyrus, 2021
Andie Day 2 days ago
You made me look twice, because I couldn't get past that thing she has on her shoulders. Don't like the bodice, but the fabric and fall of the skirt is nice. Now, why didn't she bother to get out of bed for this?
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#21
Tayla Parx, 2022
#22
Shawn Everett, 2025
#23
Dawn Richard, 2024
Andie Day 2 days ago
Agree. What was the point of ruining a lovely gown? If she wanted some decorations, why not have it be a shawl or a small headpiece?
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#24
Joy Villa, 2015
Andie Day 2 days ago
Snow fence it is! Cheap, get it at any construction site. Just an excuse to show off her body. Seriously, put clothes on. Everybody keeps showing their bits and butts, and it gets old.
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Petra Schaap 2 days ago
If this was a Dutch girls Queensday outfit in 2005 on Craftster, then yes. Other wise: NO.
Charlotte 2 days ago
Was dressing in snow fence a political statement or something? Genuine question, I don't know who this is
Lynchamigsakta 2 days ago
It looks like she made it with one of those 3d pens the night before
#25
Madonna, 1999
At the 41st Grammy Awards, Madonna reminded everyone why reinvention is practically her brand.
The singer stepped out in a bold red Jean Paul Gaultier kimono-style outfit while performing at the final Grammys of the 20th century.
Her glossy red ensemble featured dramatic sleeves, a structured waist, and matching red boots.
“I always loved it, but as our society evolves, it’s clear there were some missteps from M in appropriating certain cultures in her work as a white artist. I used to love this, but now I look back and kind of cringe,” wrote one user.
Zoe Vokes 2 days ago
It was done intentionally. The dress is kimono themed and the makeup is a heavy white base that Japanese Geishas wear
Load More Replies... persephone134 2 days ago (edited)
Madonna always tried to set new trends. Here she sports cultural appropriation way before it was a term.
LakotaWolf (she/her) 2 days ago
The Japanese generally do not view the wearing of a kimono by a non-Japanese person as "cultural appropriation". They usually see it as a form of appreciation for their culture and history. The perception of "cultural appropriation" is primarily a Western perspective.
Load More Replies... StumblingThroughLife 1 day ago
She looks like a painted ghoul (IMO) Just accept you're getting old like the rest of us in our 60s, lol.
#26
Lady Gaga, 2011
If there’s any celebrity who treats the Grammys like performance art, it’s Lady Gaga. After she arrived at the 2011 ceremony sealed inside a giant egg, no one was exactly surprised.
The oversized “vessel designed by Hussein Chalayan was carried down the red carpet by models in beige latex, which instantly became one of the most bizarre entrances in Grammys history.
Her stylist Nicola Formichetti said that the singer was “in incubation”, preparing for the debut performance of Born This Way later that night.
Surprisingly, Gaga was inside the egg for roughly 72 hours.
"It was a very creative experience. It was time for me to really prepare and think about the meaning of the song,” she told during an appearance on Today.
While it was a stunt of method artistry for Gaga, the internet had other interpretations.
“Why are you inside an egg?” one person asked bluntly.
“I can’t wait until they roll her up on stage to get her awards,” another joked.
“Quick! The egg market is now booming! BUY BUY BUY,” someone else wrote.
Others found a practical upside, with one comment noting, “I must say this is the most ingenious way to avoid talking to the media on the red carpet.”
Zoe Vokes 2 days ago
“Surprisingly, Gaga was inside the egg for roughly 72 hours” is nonsense. No way
LakotaWolf (she/her) 2 days ago
Yep, unless she was literally catheterized and wore diapers, it's nonsense. And: " 'The tank at the Grammy's only had 30 minutes worth of oxygen in it so Gaga's full of it for saying she was in that egg for hours!"' a source close to the singer told RadarOnline." Perhaps she slept in it and curled up in it often (while it remained open prior to the event) over the course of three days, but no way she actually was "inside" of it for 72 hours straight.
Load More Replies... LakotaWolf (she/her) 2 days ago
Unless she was literally medically catheterized and wore diapers, there's no way she was in the egg for three days. And: " 'The tank at the Grammy's only had 30 minutes worth of oxygen in it so Gaga's full of it for saying she was in that egg for hours!"' a source close to the singer told RadarOnline." Perhaps she slept in it and curled up in it often (while it remained open prior to the event) over the course of three days, but no way she actually was "inside" of it for 72 hours straight.
Load More Replies... StumblingThroughLife 1 day ago
That's a lot of sweaty Bettys (and Bobs) there. Ugh 😅😅. As for the egg: anything goes re: attention.
#27
Nicki Minaj, 2012
At the 2012 Grammys, the rapper arrived in a custom red Versace robe that looked part nun’s habit, part high-fashion Little Red Riding Hood.
The flowing satin gown featured a giant embroidered Medusa head on the skirt. She took things a step further by arriving with an escort dressed as the Pope, instantly turning the red carpet into a visual moment.
She paired it with red gloves.
Social media quickly shared their reactions with one writing, “All the girls during this time were very controversial with their religious moments and illuminati moments.”
“It's giving Roman Holiday from Shein,” wrote another,
Tha Monkey 1 day ago
I actually like this. It's a stunning color, which looks amazing on her, it's well made (judging by the one picture), and it is unusual enough to make her stand out, without showing off all her bits and hou-has. 10/10.
#28
Harry Styles, 2023
Harry Styles has never been afraid to dress a little left of center, and at the 2023 Grammys, he fully leaned into that reputation.
The pop star donned a low-cut, chest-baring jumpsuit that sat somewhere between chic fashion experiment and theatrical costume.
Designed by Egonlab in collaboration with Swarovski, Styles ensemble featured a rainbow patchwork pattern covered in more than 250,000 crystals.
The sparkly harlequin-style jumpsuit showed off his chest tattoos. Styled by his longtime collaborator Harry Lambert, the look was paired with white boots, chunky rings, and his signature necklace.
Social media users weren’t exactly convinced by his looks.
“He’s so cute, but I lowkey think he looks like a member of the circus,” one person wrote.
“No, no, no. It’s Pepino, the clown,” another joked.
“It’s a kindergarten quilt,” someone else commented.
Others were more critical, with one saying, “His stylist needs to find a new profession, his outfits are never it.”
Another added, “He puts absolutely no effort into his looks, and his stans pretend he’s breaking barriers. His style was honestly better in One Direction.”
Mavis 2 days ago (edited)
You know that feeling when you accidently send your kid to preschool in overalls and then you worry all day how they will manage going to the toilet.
Andie Day 2 days ago
Or you worry your kid ran away and joined the circus.
Load More Replies... LakotaWolf (she/her) 2 days ago
I don't HATE it, but I do wish the front/center wasn't so low-cut. Not that I'm offended by seeing male "cleavage", but because it looks bizarre this way. If the cut was higher, like around his collarbones, it would at least look like a normal (if unhinged-colored) bodysuit.
LakotaWolf (she/her) 2 days ago
Otto, that actually makes it gorgeous though. It looks amazing and MUCH better with a ruffly shirt!
Load More Replies... StumblingThroughLife 1 day ago (edited)
Oh, God! It reminds me of the horror of being a kid/mid-teens through the 70s. Especially after admiring clothes in the 60s, first.
#29
Chrissy Teigen, 2025
AtMostAFabulist 2 days ago
Yes, people are naked under their clothes. Do we really need to see it all the time?
Andie Day 2 days ago
They all do it. That's because they're unique snowflakes and want everyone to know. The music in their brain is always I'm too s**y for my shirt Too s**y for my shirt So s**y it hurts
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Chloe Davis 1 day ago
Looks like she dropped the rest of her dress on the floor leaving just the lining on
#30
Julia Fox, 2025
Andie Day 2 days ago
Put some d**n clothes on. No wonder you need rubber gloves to handle that ugly outfit. And you have too much lip filler. Look like a duck.
Lil be lil 17 hours ago
She looks like she could clean your clock too! While giving you a bj...puff mouth.
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What do you think ?
Nancy Bania 2 days ago
If the goal for these people was to look as stupid or as naked as possible then I guess they're all spot on.
Otto Katz 2 days ago
Cyndi Lauper looked wonderful Full of joy, color, happy She didn't show her bits, could walk, sit, and enjoy her experience
Load More Replies... keyboardtek 2 days ago
I think the clothing designers must have all taken that bad LSD at the same party.
Mavis 2 days ago
Because Censori cant get any more naked, if I was on her PR team this year Id go the complete opposite and cover her from head to toe in black garbage bags.
LakotaWolf (she/her) 2 days ago
They have ego. Massive ego. (Most of them.) And the need/want to be the center of attention and stay relevant.
Load More Replies... StumblingThroughLife 1 day ago
#NarcissisticAttentionSeekers. That's all it boils down to, IMO.
Nancy Bania 2 days ago
If the goal for these people was to look as stupid or as naked as possible then I guess they're all spot on.
Otto Katz 2 days ago
Cyndi Lauper looked wonderful Full of joy, color, happy She didn't show her bits, could walk, sit, and enjoy her experience
Load More Replies... keyboardtek 2 days ago
I think the clothing designers must have all taken that bad LSD at the same party.
Mavis 2 days ago
Because Censori cant get any more naked, if I was on her PR team this year Id go the complete opposite and cover her from head to toe in black garbage bags.
LakotaWolf (she/her) 2 days ago
They have ego. Massive ego. (Most of them.) And the need/want to be the center of attention and stay relevant.
Load More Replies... StumblingThroughLife 1 day ago
#NarcissisticAttentionSeekers. That's all it boils down to, IMO.
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