In a 2002 telecasting audience , Connie Chung reportedly need then-16 - year - old Mary - Kate and Ashley Olsen if they were virgins . Ashley " was like , ' That ’s personal . Why would you be expect a 16 - year - old that interrogative sentence in the first place ? ' "

Warning: This post mentions eating disorders.

Looking back at old talk shows and publications, some of the questions that interviews thought were appropriate to ask celebrities — mostly young women — are unbelievable.

Here are 13 wild and inappropriate questions I cannot believe interviewers had the audacity to ask celebs in the ’00s:

1.In 2003,Diane SawyeraskedBritney Spearsabout losing her virginity and what she’d tell her then-12-year-old little sister, Jamie Lynn, about sex before marriage.

Watch the full interview below, with this part starting at the 27:57 mark:

2.In a 2002 TV interview, Connie Chung reportedly asked then-16-year-old Mary-Kate andAshley Olsenif they were virgins. Ashley “was like, ‘That’s personal. Why would you be asking a 16-year-old that question in the first place?'”

reflect a year later , Ashley toldRolling Stone , " I get down really angry and defensive . "

3.In 2004,Oprahspoke to Mary-Kate and Ashley Olsen about rumors they both had eating disorders. In response, they said that they tried “not to read the good or the bad” things about themselves in the press, and then the host abruptly changed the subject to their clothing sizes.

Here’s the full clip:

The Olsen parallel 2004 interview with Oprah#olsentwins#oprahwinfrey#interview#fyp#2000s#tw

4.At the 2007 Virgin Fest, aMUCHinterviewer asked Alex Turner and Jamie Cook of the Arctic Monkeys a sexual question about their famous peers — which they basically refused to answer.

Watch the full clip below, with this part happening at the 3:36 mark:

5.In 2004, a panel of news anchors kept askingJanet Jacksonabout her recent wardrobe malfunction during the Super Bowl halftime show. However, herWhy Did I Get Married?costar Tyler Perry answered for her, redirecting the conversation to their movie.

Watch the full clip below, with this part begining at the 2:04 mark:

6.When Leighton Meester appeared onEllenin 2009, she seemingly tried to avoid talking about part of her childhood, but the host blurted it out.

Here’s the full clip, with this part starting at the 0:58 mark:

7.In 2007, David Letterman turned an interview that was supposed to be about Paris Hilton’s new perfume into one about her and Nicole Richie’s recent experiences in jail.

On a 2021 episode of her podcastThis Is Paris , she said , " That was off limits and he would not hash out it , and we would only be there to boost the perfume and my other business venture . I felt like it was a safe office because I ’d been cash in one’s chips on Letterman for so many years .   He ’d always have fun with me and jest around , but I thought he would keep his countersign on this and I was wrong . "

Watch the full clip below, with this part starting at the 0:43 mark:

8.When Emma Watson appeared on theLate Show with David Lettermanin 2009, he held up a picture of her recent wardrobe malfunction and made her address it in front of a live studio audience.

You can see the full clip at the 0:13 mark below:

9.In 2008, Ellen brought up rumors that Mariah Carey was pregnant and then pressured her to drink to prove they weren’t true, essentially forcing her to announce her pregnancy.

In 2020 , Mariah toldVulture , " I was passing uncomfortable with that moment is all I can say . And I really have had a hard time grappling with the aftermath . I was n’t ready to say anyone because I had had a miscarriage … I did n’t savor that moment . "

Watch the full clip below:

10.When theAdvocateinterviewed Anne Heche in 2001, the interviewer asked if her then-husband, Coleman Laffoon, had “a same-sex experience in his past that would have left him open to a broader worldview.” She replied, “One, that’s none of my business or your business to even ask that question, and it’s completely out of line.”

The interviewer tried to apologize , but Anne go on , " This is not an article about Coley … I’m finished with this conversation . You have got to be kidding me , after everything I have given you , you are now asking me about my husband ’s sexuality ? That is flooring to me . "

11.In 2005, Howard Stern asked Emma Bunton about rumors David Beckham was cheating on her former Spice Girls bandmate, Victoria Beckham. Then, he told her she’d have to take off her clothes if she didn’t answer.

Here’s the full clip, with this part starting at the 13:20 mark:

12.In 2002, Howard Stern and his coworkers tried to take bets on how much Anna Nicole Smith weighed and get her to step on a scale live on air.

Here is the full interview, with this part beginning around the 24:10 mark:

13.And finally, when Anderson Cooper interviewed Lady Gaga on60 Minutes Overtimein 2009, he brought up rumors that she had a penis and questioned why she didn’t confirm or deny them.

The National Alliance on Mental Illness helpline is 1 - 888 - 950 - 6264 ( NAMI ) and provides selective information and referral services;GoodTherapy.orgis an association of genial wellness professionals from more than 25 countries who support efforts to reduce harm in therapy .

TheNational Eating Disorders Associationhelpline is 1 - 800 - 931 - 2237 ; for 24/7 crisis support , text “ NEDA ” to 741741 .

A little serial dating never killed anyone. 📱🔪 F Marry Kill starring Lucy Hale and Virginia Gardner is now playing in select theaters and on digital.Watch the Trailer Now!

closeup of diane and britney during the interview

ABC / Viayoutube.com

Article image

closeup of the sisters sitting for the interview saying they are petite girls

interviewer asks them, who do you wish was a virgin

the news segment showing the interview

leighton talking to ellen

ellen going on to confirm that her parents were in prison

david asks her how she liked being in jail

letterman showing off a photograph to the audience and emma having to saying, at least i'm wearing underwear

ellen getting up to get champagne

anne and coleman standing together

howard telling emma that her dad isn't there to protect her and she'll have to take her clothes off

howard saying, i'll show you my penis if you get on the scale

lady gaga answering that her fans don't care and neither does she

F Marry Kill Movie

F Marry Kill Movie

F Marry Kill Movie