5 Boyfriends Who Ruined Everything

5 Matty Healy

Taylor Swift is in the middle of a multiple-record-breaking tour, but you’d hardly know it from the headlines. They’re a lot more concerned with the all-but-confirmed rumors that she’s dating The 1975’s Matty Healy, who is at best the kind of “artist” who thinks pretending to be racist and sexist is funny and at worst just those things.

The biggest controversy uncovered in the resulting clusterfuck was racist comments made about Ice Spice on a podcast Healy appeared on and seemed to find hilarious, which really put a damper on Swift’s subsequent collaboration with the rapper. Although everyone involved has claimed the project was in the works long before the Healy shitstorm, some fans accused Swift of doing damage control with the stunt, and considering it’s the first time she’s ever collaborated with a Black woman, that’s not an unreasonable accusation.

A big group of fans initially responded by petitioning Swift to rethink her choices because all they know how to do in the face of conflict is scream “DELETE THIS” until their eyes turn black and they start hovering upside-down, but for possibly the first time in her career, diehard Swifties are very publicly turning their back on her. They’re writing op-eds, canceling pre-orders, selling tickets, maybe even going outside. Of course, someone asked Healy what he thinks about all this, and he accused fans of “either lying that (they) are hurt, or (being) a bit mental for being hurt.” 

Matty, could you just…?

4 Sid Luft

In the early 1950s, Judy Garland’s career was in a bit of a slump. She was effectively blackballed from the movies in 1950 when studios got sick of dealing with the substance abuse problems they created, so Garland’s only means of making money were live performances, but her ensuing tour was such a success that she married her tour manager, Sid Luft, when it seems like a nice thank-you note would have sufficed.

Luft decided his next project would be to revive Garland’s film career, so he bought the rights to A Star is Born and somehow not only got it made, he got it made good. At the end of production, everyone agreed they’d made a kick-ass movie that just needed one more song from Garland — except Luft. He insisted they needed an entire medley of songs to really showcase his wife’s talents, in case anyone was somehow unfamiliar with them.

Director George Cukor and composer Ira Gershwin — you know, people whose names you might actually recognize — tried to convince him that was insane, that it would force cuts in more essential parts of the movie and bring its pace to a grinding halt. Still, Luft ordered the expensive sequence, knowing cuts would need to be made elsewhere, then took off on vacation. This alarmed his wife, who pointed out that, as producer, he should really supervise such extensive editing, but hey, how often do the husbands of incredibly famous movie stars get to go to the French Riviera? It’ll be fine, right?

It was not fine. Even after being cut to incomprehensible smithereens that droves of fans nevertheless turned out to see, the movie was too long for theaters to show more than a few times a day, so it barely made back its considerable budget. What was supposed to be Garland’s comeback ended up being the final nail in her coffin, and the studio resented the Lufts so much that it’s believed they conspired to deny her the Oscar. Do you know how mad Hollywood has to be not to award movies about Hollywood?

3 William Godwin

These days, Mary Wollstonecraft is best known as the mother of Mary Shelley and grandmother of Frankenstein, but she was the Betty Freidan of her time, most famously publishing A Vindication of the Rights of Women at a time when few people had ever stopped to consider that women might have rights. When she died following the birth of the inventor of science-fiction in 1797, her husband of just six months, William Godwin, was devastated. He became determined to finish her work, and for the next several months, he sealed himself off from the world and pored over her unpublished manuscripts and correspondence. What emerged was a meticulous and lovingly crafted biography of a woman Godwin considered to have no earthly equal that destroyed her reputation for the next century.

The thing is, Wollstonecraft had a complicated life. It included a lot of family drama, a “strange, passionate” “friendship” with another woman, several whirlwind love affairs, an illegitimate child with an American adventurer (probably the most serious crime for a British woman in the late 18th century), and at least two suicide attempts. None of this fazed Godwin, himself a radical philosopher and proponent of “free love,” but it would count as a juicy beach read even today, so he had to have known how much it would scandalize the Georgian public. The family members and lovers mentioned were furious, and critics ripped Godwin’s account of his wife’s “whoredoms” to shreds. It wasn’t until the suffrage movement of the 20th century that women began to re-reconsider that whore’s work.

2 DDG

Since the world is stupid, the release of 2023’s The Little Mermaid was way more controversial than it had any right to be, and its star, Halle Bailey, had to approach the PR tour as delicately as a dog with a bag of meth in its mouth. Unfortunately, her boyfriend, rapper DDG, has failed to help at every turn.

In fact, he keeps creating bad press for her — getting caught sliding into his ex’s DMs, publicly insulting her costars, etc. — so regularly and timed so well to various milestones in the movie’s marketing schedule that some fans believe he’s deliberately sabotaging her. Right up to the day the movie was released, instead of promoting it, she was defending her relationship, unconvincingly.

To be fair, Bailey knows how bad this all looks. In an interview with Glamour, she marveled, “It’s really funny how people look at you (as) still being this young girl, still being this innocent, untouchable thing. I appreciate that as I venture into adulthood, I’m able to make my own decisions.” In other words, what is being 23 for if not having terrible relationships?

1 Alfred Stieglitz

When Georgia O’Keeffe sent some of her art to a friend in New York City, it was both the best and worst decision of her life. The friend showed it to Alfred Stieglitz, a photographer and art dealer who was immediately taken with O’Keeffe’s work and also O’Keeffe. They had about the relationship you’d expect between a twentysomething emerging artist and a married fiftysomething established in the industry: He exhibited her work, threw himself into its promotion and took a lot of naked pictures of her.

His most arguably lasting contribution to her art, however, was one that plagued her for the rest of her life. Stieglitz was a Freudian, because of course he was, so he decided that O’Keeffe’s paintings of flowers actually represented female genitalia, an interpretation that gelled with the male art critics who attended her shows and apparently only spoke to Stieglitz about them. For the next half century, O’Keeffe had to repeatedly, politely inform people that when they “read erotic symbols into my paintings, they’re really talking about their own affairs.” In other words, “That’s a flower, you weirdo.”

O’Keeffe and Stieglitz eventually got married, and shockingly, he wasn’t a great husband. Their marriage was marred by infidelity and mental health issues, but it lasted more than 20 years until his death. O’Keeffe ended up outliving him by 40 years, but thanks to him, she did it as “that lady who paints vagina flowers.”