The Most Uncomfortable Taylor Swift Moments

Taylor Swift has come a long way from crying on her guitar. After she got her first break with "Teardrops on My Guitar," she turned her tears into lucrative breakup ballads and pop songs that earned her a reputation for being one of the most famous artists of her generation. And don't let her innocent act fool you, because she's got a "blank space" and she just might write your name. 

Music aside, the Grammy-winning artist has battled criticism about her love life and personal relationships ever since she became famous. From her current dating life to her exes to whomever she might be alluding to in her many breakup tracks, Tay can't seem to catch a break when it comes to the media. While she's steadfast in maintaining her artistic integrity and keeping her private business private, it's led to some pretty uncomfortable interviews over the years. 

The "Red" singer has been known to have a beef or two over the years as well, from fighting with Katy Perry over backup dancers to Scooter Braun selling the rights to her music. Swift has a "big reputation" and it's not always her music that has people talking. Good thing for her and Swifties everywhere, they know a thing or two about shaking it off. I'ma let you finish — but we're taking a look at the most uncomfortable Taylor Swift moments over the years. 

We can't write about Taylor Swift's most awkward moments if we don't mention the infamous Kanye West microphone grab. If you happened to miss one of the most iconic and infamous media moments of all time — we'll fill you in. During the 2009 MTV Video Music Awards, Swift won the award for best female video for her track "You Belong With Me," but her Ye rudely interrupted her acceptance speech, jumping onstage to deliver his unwelcome opinion. 

The rapper grabbed the microphone and said, "Yo, Taylor, I'm really happy for you, I'ma let you finish — but Beyoncé had one of the best videos of all time." The moment went down in pop culture history and prompted the rapper to apologize and admit he was out of line. The "Jesus Walks" rapper took to his blog after the show to issue an apology in his typical all-caps, writing: "I'M SOOOOO SORRY TO TAYLOR SWIFT AND HER FANS AND HER MOM ... I'M IN THE WRONG FOR GOING ON STAGE AND TAKING AWAY FROM HER MOMENT!"

West apologized to Swift later via phone call, and the two put the beef to bed shortly after. The "Blank Space" singer even presented West with the Video Vanguard Award at the 2015 VMAs and poked fun at their past debacle. "I'm really happy for you, and I'ma let you finish — but Kanye West has had one of the greatest careers of all time!" she said.

Taylor Swift may have put that Kanye beef to bed, but it was only the calm before the storm. The two artists were embroiled in a huge feud when Ye dropped his track "Famous" in 2016, in which he raps: "I feel like me and Taylor might still have sex/Why? I made that b**** famous." While Ye claimed Tay approved the song, Swift painted a different picture. In her 2016 Grammy acceptance speech, she quipped: "There are going to be people along the way who will try to undercut your success or take credit for your accomplishments or your fame," seemingly alluding to the controversial track. 

Kim Kardashian defended her then-husband in an interview with GQ, claiming the pop star approved the lyrics, which Swift's representatives denied. The rapper later released a music video for the track featuring him in bed with a naked Swift statue. Shortly after, Kardashian released video footage of West's phone call with Swift she said the lyrics were "like a compliment," adding, "I mean, I don't think anybody would listen to that and be like, 'Oh, that's a real diss.'"

Swift clapped back, writing in a since-deleted Instagram post: "Where is the video of Kanye telling me he was going to call me 'that b****' in his song? It doesn't exist because it never happened. You don't get to control someone's emotional response to being called 'that b****' in front of the entire world."

Taylor Swift is no stranger to questions about her dating life. The singer constantly dodges questions about who she's with, who her songs are about, and what she thinks of her exes — despite many attempts to shift the focus back to her music. Fans were outraged when a clip from 2013 resurfaced, featuring Swift in the hot seat on the "Ellen DeGeneres Show" and prompting viewers to question the lengths to which DeGeneres went to get answers about Tay's love life.

In the video, the host continues to try and ship a nonexistent relationship between Zac Efron and Swift even after the artist insists multiple times that the two are just friends. DeGeneres then set up a slideshow of pictures featuring Swift photographed with several men and asked her to ring a bell on the suitors she had dated. A visibly uncomfortable Swift attempted to get out of the game, saying: "This is the one thing that I have, like the one shred of dignity that I have ... People go and make guesses about it, and the only thing that I have is that one card." 

After the talk show host prompted her to ring the bell, Swift said: "Do you know how bad this makes me feel?" She copped out of the game adding, "I don't want to. They'll send me angry emails, and I don't want to get them," before DeGeneres rang the bell multiple times herself.

It seemed Taylor Swift would never live down the infamous Kanye West moment — especially when others kept recreating the event at other award shows. In 2013, Swift won the award for favorite country artist at the People's Choice Awards, but an awkward moment ensued when she tried to accept the award from presenter Olivia Munn. "The Newsroom" actor didn't return Swift's embrace and then proceeded to say, "If you want to thank me first, it makes most sense," before grabbing the award back from the singer. "Absolutely, yes you first," Swift joked, adding, "This always happens."

The celebratory moment was anything but celebratory when Munn quipped back, "And it will always happen Taylor, this is your lot in life," with Swift solely responding: "I know." Munn ultimately let the star have her moment, saying: "I'm not going to be this person" before exiting the stage. Tay got Kanye'd by the actor — prompting the action to become its own verb. "Kanye'd" was born, whether Swift liked it or not. 

Munn admitted to E! afterward that "It was a whole bit that we planned and it was supposed to be funny," adding that "I guess some people didn't [know we were joking]. But at least the people that mattered knew that we were joking."

Journalistic integrity was the last thing on one reporter's mind when she crossed the line with Taylor Swift. In 2015, Swift went home empty-handed from the Grammys and also had an awkward run-in with an Entertainment Tonight reporter. In the clip, the reporter shows off Swift's outfit telling her, "I just wanted to show the legs, 'cause as I was telling you ahead of time, you're going to walk home with more than maybe just a trophy tonight, I think lots of men." Swift gave her an immediate death stare, responding: "I'm not going to walk home with any men tonight ... I'm gonna go hang out with my friends, and then I go home to the cats," adding, "Men get me in trouble."

It isn't the only time the "Love Story" singer battled sexism in the media. In an interview with 2DayFMSydney, the singer clapped back at the haters who criticize her for making songs about her love life. "Frankly, that is a very sexist angle to take," she said, adding, "No one says that about Ed Sheeran. No one says that about Bruno Mars. They're all writing songs about their exes, their current girlfriends, their love life, and no one raises a red flag there." 

T-Pain had some interesting choice words for Taylor Swift onstage while hosting the iHeartRadio Music Awards in 2019. During the show, the rapper spoke about how the two first met in the most cringeworthy way possible. "Taylor, I never apologized to you," he started. "The first time we met — you're so much taller than me, that I thought you were standing on something." He then went on to add, "Without looking down, I tried to stand on whatever I thought you were standing on and — bam! Headbutted you right in the boob," he joked. "I'm so sorry. That was not my intention."

There's no telling what Swift was thinking during the awkward — and very public — exchange, but she seemed visibly uncomfortable in the audience. As she looked on awkwardly, fans took to X to share their reactions. "This @TPAIN exchange w @taylorswift13 was the most awkward thing I've seen in the history of forever. #iHeartAwards2019 #eekface," one viewer tweeted. "Taylor Swift wasn't digging the TPain joke," another tweeted alongside a photo of Swift's reaction. Despite the cringey moment, Tay did take home the award for best music video for her track "Delicate" as well as tour of the year for her album "Reputation."

If you're interviewing Taylor Swift ahead of an award show, you should probably know whether or not she's actually up for any awards. One journalist learned that the hard way ahead of the 2012 Billboard Music Awards when she had an awkward run-in with Swift backstage. The "Delicate" singer was at a loss for words when the reporter told her: "And you've got another couple of awards that you're up for," to which she replied, "Really?" 

After the interviewer awkwardly responded, "Yeah, maybe," Swift said, "I don't even think I do." The woman quickly bounced back from the slip-up, telling the artist, "Well maybe we'll make some up ... I tell you what, we're gonna give you an award right now for being the sweetest person on camera for my mistake." While she might have given a lesson in journalism 101, Swift took the interview in stride. She did, however, take home the award for woman of the year that year, but she had known about the prestigious honor the year prior.

All eyes are on Grammy nominees during camera pans when the winners are about to be named. Close-up shots tell a bigger story, whether an artist seems shocked to lose or plays it safe by keeping their reactions undetected. Taylor Swift had an interesting reaction of her own during the 2014 Grammy Awards when she was up for album of the year for her record "Red." In a video clip from the show, Swift seemed shocked for a moment when presenter Alicia Keys announced that "Random Access Memories" by Daft Punk had taken home the award. The first syllables seemed to make Swift sense that she had won the award instead, drawing an awkward reaction. 

The singer spoke about the cringeworthy moment in an interview with Grammy Pro, saying: "When they announced the album of the year winner it was like, 'And the album of the year goes to ... "Reeeeeandom Access Memories," Daft Punk!' And they really dragged out the 'reeee.' And for a second there, I kind of thought we had it, and we didn't. I remember not going to after-parties, I went home and I cried a little bit, and I got In-N-Out Burger and ate a lot."

Taylor Swift has long endured jokes about her love life. But the star had enough in 2013 after presenters Amy Poehler and Tina Fey made reference to her at that year's Golden Globe Awards. In a video clip of the event, Fey said, "You know what Taylor Swift? You stay away from Michael J. Fox's son." To which Poehler joked, "Or go for it!" The actor then said, "No, she needs some me time to learn about herself," seemingly shading Swift for her serial dating.

Swift clapped back in an issue of Vanity Fair. "You know, Katie Couric is one of my favorite people because she said to me she had heard a quote that she loved, that said, 'There's a special place in hell for women who don't help other women,'" she said. While the quote was attributed to former Secretary of State Madeleine Albright during a 2006 speech at a WNBA event, the message was clear. Swift was never, ever, getting back together with Poehler and Fey. 

Fey addressed the drama, telling Entertainment Tonight, "I did not see that one coming. It was a joke. It was a lighthearted joke." As for Poehler, she was more sympathetic, telling The Hollywood Reporter: "Aw, I feel bad if she was upset. I am a feminist and she is a young and talented girl." Eventually Swift cleared the air with Poehler at the 2020 Golden Globes when they presented together.

Swifties everywhere were in for a wild ride in 2015. Taylor Swift and Nicki Minaj's social media spat began when Swift's "Bad Blood" music video was nominated for video of the year at the VMAs, but Minaj's "Anaconda" video didn't get a nod. The "Moment 4 Life" rapper took to X, writing: "Lol u guys did we miss the deadline?? #MTV?" and later tweeting: "If your video celebrates women with very slim bodies, you will be nominated for vid of the year."

The "Teardrops on My Guitar" singer saw that as a shot at her "Bad Blood" video. She responded in a since-deleted tweet: "@NICKIMINAJ I've done nothing but love & support you. It's unlike you to pit women against each other. Maybe one of the men took your slot." Minaj then quipped back with: "Huh? U must not be reading my tweets. Didn't say a word about u. I love u just as much. But u should speak on this." Swift later apologized for misinterpreting the tweets, writing: "I thought I was being called out. I missed the point, I misunderstood, then misspoke. I'm sorry, Nicki." 

The "Barbie Dreams" rapper accepted her apology and the artists buried the beef. Although Swift went on to win that year's video of the year award, there was no longer any "bad blood." The two went on to perform a mash-up of "The Night Is Still Young" and "Bad Blood" together during the awards show. 

With Taylor Swift's "Eras" tour projected to generate over $5 billion dollars in consumer spending alone, it is set to be the highest-grossing tour to date of any artist ever, potentially. That said, the show must go on. Even if that means that Swift has to cough up a bug. 

The "Cruel Summer" artist had to stop the show briefly during a Chicago tour stop when an unwelcome insect happened to land in her mouth. How the bug happened to land on Swift in a sea of thousands is another story entirely, and the exact species of the bug remains unknown. But in a video clip from the show, the singer is seen coughing before saying: "I swallowed a bug, I'm so sorry," before joking, "Oh, delicious ... Is there any chance that none of you saw that?" Pop stars — they're just like us, right?

Taylor Swift was in for a rude awakening when she stopped by "The Tonight Show Starring Jimmy Fallon" in 2019. During her sit-down interview, Fallon surprised the singer by revealing to the audience that she had laser eye surgery. "Can you see me by the way?" the talk show asked her while she confusingly responded, "Uh ... Yeah." Fallon then asked her, "Didn't you just get LASIK surgery?" A surprised Swift admitted: "I did, how do you know that?" 

Fallon questioned the singer on whether or not she took painkillers after the surgery, to which she replied: "They definitely give you some pretty hardcore pills after you have a laser in your eye — what is going on?" The host admitted Swift's mother had provided producers with video footage of the singer post-surgery and loopy on painkillers. In the video, Swift — decked out in protective eyewear — attempts to pick a banana and then gets visibly upset when she admits, in tears: "That wasn't the one I wanted." When her mother attempts to help her grab another banana, Swift asks her, "But what do we do with this [banana] now? ... It doesn't have a head." When her mother warned her not to fall asleep eating the banana, the artist quipped back: "I'm not asleep, my mind is alive." 

The "Lover" singer was in shock at how Fallon pulled off getting the footage, and bananagate lives on in Swift history.