Lifestyle Style Anna Wintour Tells Kendall Jenner About the Worst Date She Ever Had: 'I Never Saw Him Again!' Spoiler alert: Wintour's dad was involved in her most cringe-worthy date By Kaitlyn Frey Kaitlyn Frey Instagram Twitter Assistant Style & Beauty Editor, PEOPLE People Editorial Guidelines Published on February 6, 2020 04:05 PM Share Tweet Pin Email Vogue editor-in-chief Anna Wintour is getting candid in a special Valentine’s Day edition of the brand’s popular video series, Go Ask Anna. In a new segment, the longtime magazine editor opens up about her personal life — specifically, the best and worst dates she’s ever been on. Supermodel Kendall Jenner (who frequently graces the pages of the magazine) appeared as one of the guests, asking the editor, “Anna, what was your best and worst date?” “Hello Kendall. I’m only going to answer this question if you agree to give me your answers to exactly the same question the next time I see you, which will be shortly,” Wintour, 70, replied. She began by detailing her favorite dates, which include spending some quality time with her children. “In answer to my best date I have to choose going to the theater with my daughter or going to a tennis match with my son,” she said. As for the worst date she’s ever been on, Wintour says it was with a man she had dated more than 40 years ago. “In terms of my worst date ever, back in then ’70s I was very, very interested in a young man who was a writer of very activist leanings, and he was always getting arrested and going to jail and getting a lot of negative press,” she explained. “My father, who was an editor of a newspaper and never exhibited any interest in my boyfriends, asked me if he could meet him,” Wintour continued. After the trio had an “extremely uncomfortable exchange” over dinner, Wintour’s father had a proposition for her then-boyfriend at the end of the night. “My dad said to the young man, ‘I know you’re interested in politics. Would you like to go to America and cover the upcoming election campaigns?'” she recalled. Wintour continued: “And he of course was stunned and immediately said yes and then he left the next day and I never saw him again! So my dad was quite cunning.” While Jenner hasn’t filled us in on her worst date just yet, Wintour did answer some other fans’ questions throughout the video — including her 2020 Oscar picks. “Hey Anna. I’ve seen almost no movies this Oscar season. If I could check out one movie, what should I watch?” one person asked. But since it was “really hard” to pick just one film she loved, the editor shared her top two. “The first one would be The Farewell which is partly set in New York and partly set in China. Great story about a woman confronting mortality with her grandmother,” Wintour said. “And the second one which is a little darker is nominated for many, many awards, has won already many awards and is called Parasite.” Gregg DeGuire/Getty Parasite has been one of the buzziest movies this awards season, even making history at the 2020 SAG Awards when it became the first foreign language film to take home the biggest award of the night: outstanding performance by a cast in a motion picture. It also won best foreign language film at the 2020 Golden Globes and is up for Best Picture at the Oscars on Sunday. As for the Best Costume Design category, Wintour praised Jacqueline Durran’s work in Little Women and Arianne Phillips for Once Upon a Time… in Hollywood.