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The Cringiest Questions Reporters Have Asked Celebs Over the Years

When Britney Spears Did an Interview with Diane Sawyer in 2003

When Britney Spears Did an Interview with Diane Sawyer in 2003

Britney Spears’s entire 2003 interview with Diane Sawyer for Primetime was just awkward. Sawyer began the segment talking about Spears’s bellybutton, called her out for biting her nails and cracking her knuckles, and then got too personal with questions about her breakup with Justin Timberlake.

She brought up Spears’s public loss of innocence over the years and distastefully asked how she felt about it. Spears was clearly very uncomfortable through it all and brushed off a lot of it with laughter. Then Sawyer brought up how 2003 had been a hard year for Spears with hurtful comments from fans, her aunt battling cancer, and her ugly breakup with Timberlake, and Spears couldn’t help but start tearing up. It was hard for us to sit through the whole thing, we can’t imagine what it was like for Britney.

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When a Reporter Asked Taylor Swift How Many Men She’s Taking Home

When a Reporter Asked Taylor Swift How Many Men She’s Taking Home

Taylor Swift has developed a reputation over the years of having boyfriend after boyfriend and writing songs about each of them. Swift has talked about not liking this kind of attention, but it still gets talked about, and people still want to know who every song is written about.

On the red carpet at the 2015 Grammys, Nancy O’Dell with ET said to Swift, “as I was telling you ahead of time, you are going to walk home with more than maybe just a trophy tonight. I think lots of men.” To which, Swift looked shocked and said, “I’m not going to walk home with any men tonight. I’m going to go hang out with my friends, and then I go home to the cats.”

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When Nicki Minaj Turned Tables on Comparison with Lady Gaga in 2012

When Nicki Minaj Turned Tables on Comparison with Lady Gaga in 2012

In Juju Chang’s interview with Nicki Minaj on ABC News in 2012, Chang asked how Minaj felt about being compared to Lady Gaga, and Minaj said, “what are the similarities? Why don’t I turn the cameras around and ask you?”

Chang responded with “wigs” and “over-the-top costumes,” but Minaj started to get annoyed and shut down each of those responses. While Minaj wasn’t annoyed particularly at Chang for bringing these up, but rather that people, in general, think these things about her, it still makes this relatively normal interview cringey to watch.

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When Power 106 LA Radio Hosts Asked Ariana Grande Sexist Questions

When Power 106 LA Radio Hosts Asked Ariana Grande Sexist Questions

When Ariana Grande appeared on Power 106’s radio show in 2015, while promoting her album Focus, one of the radio hosts asked her, “if you could use makeup or your phone one last time, which one would you pick?”

To which Grande responded, “is this what you think girls have trouble choosing between?” Then one of the hosts asked, “can you really go anywhere without your cell phone?” and Grande clapped back, “yes, many hours, absolutely, I have to do it. When I’m at a dinner table I like to be present, and talking, and eye contact” when a host then tried to turn it around by saying, “ladies, learn!” but Grande just continued with “boys, learn!” Don’t mess with sexist comments around Ariana Grande. She will take none of it.

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When Rihanna Was Asked a Personal Question During a Movie Promotion

When Rihanna Was Asked a Personal Question During a Movie Promotion

During a panel in London for the promotion of her movie Battleship in 2012, amidst rumors of a fling between Rihanna and actor Ashton Kutcher, a reporter began mentioning to Rihanna that she is very personable and has a good relationship with her fans and that she is obviously successful in her career, but the reporter wondered if she was as happy in her private life as she is in her career.

She went on to ask if a certain Mr. Ashton Kutcher would make an appearance at the premiere of the movie in London, to which Rihanna responded, “how disappointing was that question.” Once the moderator said they should move on, Rihanna followed up with, “I’m happy, and I’m single, if that’s what you’re really asking” clearly bothered by this invasion of privacy.

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When Cara Delevinge Had an Uncomfortable Interview with Good Day Sacramento

When Cara Delevinge Had an Uncomfortable Interview with Good Day Sacramento

In a remote interview promoting her movie Paper Towns, Cara Delevinge was definitely not vibing with the anchors of Good Day Sacramento. They made comments and asked her questions about how tired she must be because of how busy she was and all of her projects being so close together, but Delevinge responded sarcastically and then truthfully with how she loves what she does so it doesn’t feel exhausting at all.

It continued to get more uncomfortable as time went on to the point where the anchors called her out on how unenthused she looked with the interview, asking if it was because the premiere had already passed and she didn’t care anymore, but based on Delevinge’s response, it was more likely because of the anchors’ presumptuous questions. Delevinge’s video stream even cut off before the scheduled time due to her uncomfortability, allowing the anchors to continue to talk about her behind her back. Definitely not a vibey interview.

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When Andy Cohen Asked Nicki Minaj Presumptuous Questions in 2014

When Andy Cohen Asked Nicki Minaj Presumptuous Questions in 2014

Andy Cohen is known to not shy away from asking very personal questions, but in one of his shows from 2014 in a conversation with Nicki Minaj, he asked Minaj questions that took her back, and she had to really try to compose herself to answer.

One he asked was “who has the biggest d*** in the music industry?” in response to a line in one of her songs, but Minaj composed herself and responded with, “I saw one penis for ten years, and that’s all I’ll say about that.” The other was a random question chosen from a viewer asking if she and Drake were single at the same time, would she sleep with him? Minaj answered with an uncomfortable, “no.”

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When Larry King Assumed Seinfeld was Cancelled Involuntarily

When Larry King Assumed Seinfeld was Cancelled Involuntarily

Jerry Seinfeld was a guest on Larry King Live in 2007 when King asked how long Seinfeld lasted, to which Seinfeld responded, “nine years.” King then asked if it was Seinfeld that “gave it up.” He wondered, “they didn’t cancel you, you cancelled them.”

Seinfeld looked a little offended and asked, “you’re not aware of this? You think I got cancelled? You’re under the impression that I got cancelled? I thought that was pretty well-documented.” King responded with, “did I hurt you, Jerry? Don’t most shows go down a little?” and Seinfeld said, “it was the number one show on television! Do you know who I am? 75 million viewers last episode!” You don’t want to get this fact messed up around Jerry Seinfeld, that’s for sure.

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When Tom Hardy Shut Down Deeply Personal Question from Reporter

When Tom Hardy Shut Down Deeply Personal Question from Reporter

During a panel at the 2015 Toronto Film Festival, a reporter from an LGBTQ+ news outlet asked Tom Hardy about his sexuality. Well, they weren’t actually that blunt in their question. The reporter mentioned how Hardy’s character in the movie he was promoting was very open about his sexuality and asked if he found it difficult for celebrities to talk to the media about their sexuality.

Hardy’s answer was in the way he responded. He asked, “are you asking about my sexuality?” The reporter answered, “uh, sure.” Hardy shut them down asking, “why?” and ending it with a “thank you.” The reporter was referring to an interview Hardy had done many years ago that mentioned he had experimented with his sexuality when he was younger, but Hardy has since said that it was a misquote. Hardy currently has three children from two heterosexual marriages. It’s just rude how the media think they deserve to know such private details of celebrities’ lives.

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When Jerry Penacoli Asked a Sexist Question to Scarlett Johansson

When Jerry Penacoli Asked a Sexist Question to Scarlett Johansson

During promotion for The Avengers in 2012, Jeremy Rinner and Scarlett Johansson sat down with Extra’s Jerry Penacoli where he asked Johansson, “were you able to wear undergarments with the costume?” in reference to her skin-tight Black Widow suit.

Johansson was set off and said, “you’re like the fifth person to ask me that today. What is going on? Since when did people start asking each other about intricacies about their underwear?” Penacoli laughed and responded, “well, it’s because it’s such a skin-tight,” but Johansson cut him off and said, “I’ll leave it up to your imagination.” Yikes.

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When Jerry Penacoli Asked ANOTHER Sexist Question to Anne Hathaway

When Jerry Penacoli Asked ANOTHER Sexist Question to Anne Hathaway

In that same year, Penacoli asked Anne Hathaway about how she got in such phenomenal shape for her character Cat Woman in The Dark Knight Rises when Hathaway got a little uncomfortable talking about her body and fitness regimen and tried to push the conversation off by saying, “it’s all the boring stuff that no one wants to do. It’s just watch what you eat and get yourself to the gym.”

However, Penacoli kept pushing her on her tight-fitting outfit in the movie and the shape that she was in to the point where Hathaway had enough and turned it around on him saying, “are you trying to lose weight? Like what’s the deal, man, you look great. No, no seriously we have to talk about this. What? What do you want? Are you trying to fit into a catsuit?”

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When Danielle Demski Forgot That Rashida Jones is Biracial

When Danielle Demski Forgot That Rashida Jones is Biracial

Rashida Jones is the daughter of Black musician Quincy Jones and white model and actress Peggy Lipton. However, Danielle Demski from TNT seemed to forget Jones’s mixed race based on her comment on Jones's appearance at the 2015 SAG Awards red carpet.

When Jones approached Demski and her co-reporter, Demski remarked, “you look like you’ve just come off like an island or something. You’re very tan, very tropical.” To which Jones jokingly responded, “I mean, you know, I’m ethnic,” to brush off the awkwardness, but Demski’s white male co-reporter made it worse by joking back with, “yeah, me too.” Big yikes.

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When Katie Couric Asked Unwanted Questions About Transitioning to Carmen Carrera

When Katie Couric Asked Unwanted Questions About Transitioning to Carmen Carrera

Carmen Carrera is a transgender woman who is a successful model and television personality. In 2014, she appeared on Katie Couric’s talk show to talk about the recent hype and petition to get Carrera to be Victoria’s Secret’s first transgender model. The interview started off light-hearted and friendly, and the two briefly covered Carrera’s physical transitioning process that she posted publicly online, but it got off course when Couric asked about Carrera’s private parts.

To that question Carrera responded, “I don’t want to talk about it because it’s really personal, and, I don’t know, I’d rather talk about my modeling stuff,” she continued with, “and showing people that after the transition, there’s still life to live.” We really admire Carrera’s courage to stand up for herself like that as well as Couric’s later apology where she admitted that it was wrong of her to ask such a personal question, and she is doing her best to learn and do better.

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When a German Interviewer Asked Lady Gaga About Her Private Parts

When a German Interviewer Asked Lady Gaga About Her Private Parts

Again with questions about private parts. Why does the media feel entitled to know this stuff about celebrities? In 2009, it was, for some reason, a rumor that Lady Gaga didn’t have female private parts, and a German interviewer spared nothing and cut straight to what she wanted to know and asked Gaga if she had male private parts.

Gaga responded with, “my beautiful vagina is very offended by that question.” This isn’t a matter of cultural differences between the conservative United States and more open-minded Europe, either. It’s simply rude to ask about people’s private parts no matter the situation. That’s why they’re private!

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When Jay Leno Asked Kanye West What His Late Mother Would Think

When Jay Leno Asked Kanye West What His Late Mother Would Think

Everyone remembers when Kanye West ran on stage at the VMAs in 2009 to interrupt Taylor Swift’s acceptance speech for best female video to say that “Beyonce had one of the best videos of all time” and how shocked everyone was at his bad behavior.

Later, in an interview, Jay Leno brought up how he had the pleasure to meet West’s mother before she died and how lovely of a lady she was. He then asked West what his late mother would’ve thought about his behavior. West was visibly stopped in his tracks and got very quiet. He appeared to even tear up slightly. Talk about uncomfortable.

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When The Kyle and Jackie O Show Hijacked a One Direction Reunion

When The Kyle and Jackie O Show Hijacked a One Direction Reunion

Harry Styles called in as a guest star on the Australian radio show The Kyle and Jackie O Show in 2019, and the hosts asked Styles if One Direction would get back together. He gave the sincere and honest answer and said that if it happens, it happens, and he wouldn’t be opposed to it because it was such a special time in his life.

However, Kyle kept pushing him and told him that they should do a free reunion concert the next year in Australia and they can put it all together for them. He started planning the whole thing then and there while Jackie supported him with several “yeah”s and Styles stuttered speechless at the audacity of this radio host.

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When Oprah Winfrey Asked Michael Jackson if He’s a Virgin

When Oprah Winfrey Asked Michael Jackson if He’s a Virgin

Here we go again with overly personal questions. In 1993, Oprah Winfrey sat down with Michael Jackson in an interview and asked off-handedly, “are you a virgin?” Jackson gasped at the question.

He responded, “how could you ask me that question? I’m a gentleman.” She also asked other unwanted questions such as “why do you always grab your crotch?” and “how much plastic surgery have you had?” Come on, Oprah! You should know better than this.
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When Paris Hilton Walked Out of an Interview with Dan Harris in 2011

When Paris Hilton Walked Out of an Interview with Dan Harris in 2011

In an interview with ABC News’s Dan Harris in 2011, Paris Hilton was asked what she thought about Kim Kardashian coming into the spotlight alongside her. He insinuated that Kardashian was overtaking Hilton’s spotlight and asked her if she ever worried about that.

Hilton calmly answered, “no,” but then looked off to the people behind the camera to tell them only with a look that she wanted out. Harris tried to continue with the interview, but Hilton simply stood up and walked out. This was not a conversation she was willing to have.

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When Robert Downy Jr. Walked Away From Deeply Personal Questions

When Robert Downy Jr. Walked Away From Deeply Personal Questions

If you know about Robert Downy Jr.’s past, then you know that it is rather dark with his drug and alcohol addictions and his relationship with his father. However, this is very personal information, and no one is entitled to know it unless Downy wants to tell them.

In an interview from 2015, Krishnan Guru-Murthy must have thought he was the exception because he asked Downy about all of these topics in one blow, which obviously caused Downy to get defensive. He said, “I’m sorry what are we doing? Bye.” And he got up and left. Boundaries exist, and interviewers know how to go right past them, don’t they?

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When Larry King Asking DJ Khaled How He Gained “All the Weight”

When Larry King Asking DJ Khaled How He Gained “All the Weight”

The conversation started out as a conversation about peace as Larry King talked about his Jewish ancestry, and DJ Khaled talked about his Palestinian ancestry. They then transitioned into talking about Khaled’s motivation for success, but things took a sharp right turn when King bluntly asked Khaled, “how did you gain all the weight?”

They hadn’t mentioned Khaled’s weight yet, so it came as a big shock to the viewers, but Khaled seemed to simply take it in stride and honestly answered, “just eating a lot, you know what I’m saying? I cut all that out. No fried food, no carbs.” He then went on to say how he wants to continue to lose weight. It looked awkward and confusing to the rest of us, but good for DJ Khaled for handling the interview like a pro.

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When a French Radio Host Asked About Hayley Williams’s Last Climax

When a French Radio Host Asked About Hayley Williams’s Last Climax

“Pardon my French” took on the full extent of its meaning in Hayley Williams’s interview with a French radio station in 2010. The host went right into asking very blunt questions like “when was the last time you got drunk?” and “what is your favorite bad word?” Williams answered very modestly to both, but the host kept asking the blunt questions in rapid-fire succession.

The next question he asked was when Williams last had a climax, to which she simply replied, “we don’t talk about that on the radio.” If we thought American interviewers were asking blunt questions, with that German reporter’s question for Lady Gaga and this French host’s question for Hayley Williams, it appears that Europeans are way more blunt about these things.

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When Today Had an Awkward Interview with Kanye West in 2010

When Today Had an Awkward Interview with Kanye West in 2010

2009 to 2010 weren't good years for Kanye West. He was viewed as the “bad guy” in all of Hollywood because of what he did to Taylor Swift at the VMAs, and all of his interviews that year seemed to cut right to his heart in the matter. He had an interview in 2010 with Matt Lauer on Today where Lauer brought up West’s infamous line from the Hurricane Katrina relief telethon, “George Bush hates Black people,” and confronted him with Bush’s reply where he said that it is untrue and that this moment was “one of the most disgusting moments of my presidency.”

This made West really uncomfortable to say the least. Then, as if this wasn’t enough, they had him talk about what happened at the VMAs and played the clip while he was talking where he could hear it and got very upset. He basically stopped the interview while still on live TV and said, “yo, how am I supposed to talk while you’re gonna run this thing while I’m talking?” When Lauer tried to recover the interview, West made sure that his view was clear and said, “please don’t let that happen again. It’s, like, ridiculous.” The interview wasn’t recovered from there.

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When Matt Damon Got Defensive with Libertarian News Channel

When Matt Damon Got Defensive with Libertarian News Channel

At a “Save Our Schools” rally in 2011, Matt Damon was in attendance with his mother, who is a teacher. While there, a Reason.TV reporter interviewed him saying that in acting, there is an incentive to work hard to keep a job, but what would happen if teachers didn’t also have that same incentive. Damon didn’t like that she assumed that the incentive for him to keep a job was why he put work into his acting and. He was also offended for his mother, who was standing right next to him, and said that teachers don’t work for incentive, why else would they take a bad salary and work long hours if they didn’t want to teach.

It got worse when the cameraman decided to jump in and said that ten percent of teachers are bad and shouldn’t be able to receive tenure. Damon’s mother asked where he even got that statistic, and the cameraman said that ten percent of people in any profession are bad, probably. Then Damon, getting even more heated, turned it around on him and said, “well maybe you’re a s***** cameraman, I don’t know.” When interviewing people at a political event, do your research beforehand and ask smarter questions than this. Come on, guys.

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When Mel Gibson Had an Uncomfortable Interview with Dean Richards

When Mel Gibson Had an Uncomfortable Interview with Dean Richards

While promoting Edge of Darkness in 2010, Mel Gibson appeared on WGN-TV for an interview with Dean Richards. They began by talking about the movie and how Gibson felt about starring in a leading role again after a long absence from the spotlight, and everything was going alright.

Then Richards asked if Gibson thinks enough time has passed from his problem with drinking a few years ago that audiences will receive him well. Gibson got very offended from that question and thought it was unfair since it was four years ago at the time, and he’s done a lot of growth since then. He told Richards to move on, and as the interview closed, Gibson said, “buh-bye, asshole.” Another lesson in not getting too personal in interviews.

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When Emma Thompson Was Tired of Talking About the Royal Wedding

When Emma Thompson Was Tired of Talking About the Royal Wedding

The royal wedding of Prince Harry to Meghan Markle was a giant conversation piece in 2018, but at a red carpet interview in 2018, a reporter kept pushing British actress Emma Thompson to share her thoughts on the upcoming event.

Thompson answered honestly that she really wasn’t keeping up with the event and would rather not talk about it, and she was much more consumed with preparing for her son’s wedding that upcoming year. However, the reporter kept pushing her and asked if she wished the couple well. Thompson responded, “obviously, yes! But I don’t know them!” Just because she is famous and British doesn’t mean she is consumed with the royals and would like to spend her time chatting about them.

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When TNT Reporters Didn’t Know that Mayim Bialik is a Real Scientist Too

When TNT Reporters Didn’t Know that Mayim Bialik is a Real Scientist Too

Most people know Mayim Bialik for playing a neuroscientist named Amy Farrah Fowler on the hit sitcom The Big Bang Theory. However, people may not know that she is also a neuroscientist in real life. Talk about a Renaissance woman! However, in a TNT red carpet interview from 2014, one reporter obviously didn’t know this fun fact, and it came across rather disrespectful.

He asked Bialik, “how many people think that you can solve calculus at the drop of a hat?” She responded, “um, I was actually trained in calculus for several years. Yeah, I’m a neuroscientist, so. You may not have known that.” Yikes, but we have to say that she did a great job carrying it on from there and managing to smooth over this awkward encounter.

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When Young Helen Mirren Derailed Sexist Questions in 1975

When Young Helen Mirren Derailed Sexist Questions in 1975

A 1975 interview with Michael Parkinson introduced Helen Mirren in a very sexist way, pointing out the conversation in the media about how they viewed her as a sex object, and Mirren entered the stage looking displeased at the statement.

Parkinson then went into the interview asking about her “equipment” which she then poked back and asked him to be more upfront about what he meant, to which he answered her "figure." The entire interview she was witty and defended herself from falling into any disgusting traps he put her through. It was definitely an unsavory interview, and now-Dame Helen Mirren handled it like the professional she is.

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When Dakota Johnson Confronted Ellen About Not Coming to Her Party

When Dakota Johnson Confronted Ellen About Not Coming to Her Party

During the holiday season of 2019, Dakota Johnson was a guest on Ellen DeGeneres’s talk show where DeGeneres brought up that Johnson had just had a birthday. She asked her, “how was the party? I wasn’t invited,” with her typical wit, but it wasn’t met with a giggle from Johnson.

Instead Johnson replied, “actually, no, that’s not the truth, Ellen. You were invited. Last time I was on the show last year, you gave me a bunch of s*** about not inviting you, but I didn’t even know you wanted to be invited.” DeGeneres said, “well who doesn’t want to be invited to a party,” and Johnson answered honestly saying, “well I didn’t even know you liked me!" This wasn’t your typical fun-spirited Ellen interview.

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When a Reporter Asked a Sexist Question to the Cast of Mad Max: Fury Road

When a Reporter Asked a Sexist Question to the Cast of Mad Max: Fury Road

At the 2015 Cannes Film Festival, during a panel for Mad Max: Fury Road, a reporter asked if, while they were reading the script, did they ever think “why are all of these women in here? I thought this was supposed to be a man’s movie.”

The question was met with silence as the reporter sat down looking proud of his question to which Tom Hardy eloquently responded, “no. Not for one minute.” Why would that reporter even think it was okay to ask that? Who thinks this nowadays?

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When Radio Hosts Reminded Dylan McDermott “Your Mom Was Killed.”

When Radio Hosts Reminded Dylan McDermott “Your Mom Was Killed.”

In a conversation about a recent project that Dylan McDermott was working on in 2018, Jim Norton and Sam Roberts, on their radio show, very bluntly brought up the fact that McDermott’s mother was murdered by saying, “your mom was killed,” as the opening to a conversation about murder.

It was very insensitive to bring it up in the first place, but then they began asking questions about her death, which we suspect McDermott wasn’t wanting to unpack in a random radio interview. McDermott responded, “yeah, I mean, I don’t really want to get into that now. I’m just here to talk about L.A. to Vegas. Yeah, it was definitely rough.” But then they kept trying to talk about it! Take a hint, and maybe take notes of normal things to talk about with strangers.

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When Barbara Walters Asked Brooke Shields About Her Sex Life...at 15

When Barbara Walters Asked Brooke Shields About Her Sex Life...at 15

All the way back in the ‘80s, Brooke Shields had a rather controversial advertising campaign with Calvin Klein Jeans. At the time Brooke was only fifteen years old. Probably, a few years too young to be seductively modeling adult apparel. The ad campaign was ultimately successful, but not without years of backlash which somewhat damaged her career.

Celebrity journalist Barbara Walters even interviewed Brooke and asked her very inappropriate questions about her sexual history. Recently, Brookes broke her silence about the insane interview with Barbara on Dax Shepard’s podcast Armchair Expert. Brooke agreed with Dax that the interview was “Practically criminal.”