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Taylor Swift‘s relationships with her boyfriends have gotten almost as much attention as her hit songs like “Shake It Off” and “Blank Space.” That’s not always a good thing. One of her most famous boyfriends went on a rant where he compared himself to a KKK grand dragon. He gave what has to be one of the worst celebrity interviews of all time.

Taylor Swift had a famous boyfriend at 19

Flashback time! According to The Independent, Swift dated singer-songwriter John Mayer from December 2009 to February 2010, when she was 19 and he was 31. Mayer is most known for his hits “Your Body Is a Wonderland,” “Waiting on the World to Change,” “Say,” “Daughters,” and a cover of Michael Jackson’s “Beat It.” Swift and Mayer also duetted on the track “Half of My Heart.” Supposedly, Swift’s song “Dear John” is aimed at Mayer. In that tune, Swift attacks a man for being unfaithful and for pursuing her when she was too young.

During a March 2010 interview with Playboy, Mayer decided it was a good idea for him to toss around the N-word casually. “Someone asked me the other day, ‘What does it feel like now to have a hood pass?'” he said. “And by the way, it’s sort of a contradiction in terms because if you really had a hood pass, you could call it ‘a N-word pass.’ Why are you pulling a punch and calling it ‘a hood pass’ if you really have a hood pass?”

John Mayer explained why he never had a Black girlfriend

Mayer was asked if Black women pursue him. “I don’t think I open myself to it,” he replied. “My d*** is sort of like a white supremacist. I’ve got a Benetton heart and a f*****’ David Duke c***. I’m going to start dating separately from my d***.” For context, Duke is a Neo-Nazi and Holocaust denier who once served as a grand wizard in the Ku Klux Klan.

Mayer then had the gall to say that, just perhaps, he truly understood the struggles of Black America. “What is being Black?” he said. “It’s making the most of your life, not taking a single moment for granted. Taking something that’s seen as a struggle and making it work for you, or you’ll die inside. Not to say that my struggle is like the collective struggle of Black America. But maybe my struggle is similar to one Black dude’s.”

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Taylor Swift’s former boyfriend apologized but didn’t address everything he said

The New York Times noted that Mayer took back his comments very quickly. On Twitter, he apologized for using the N-word. In his opinion, Mayer was trying to use it in an anti-racist manner. He said it was wrong for him to try and “intellectualize” the slur and that he would permanently remove it from his vocabulary. He did not directly address his comments on Duke or the struggles of Black America.

The “Still Feel Like Your Man” singer also retracted his statements to Playboy in a concert. Mayer said he was trying to be clever when he made comments that hurt people he loved and who loved him back. He condemned his behavior as selfish, greedy, and arrogant. Still no mention of Duke.

While Mayer was a big star in the 2000s, he was mostly ignorable in the 2010s. Meanwhile, Swift would only rise and rise in the music industry.