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The Ultimate Valentine’s Day Playlist: Popular Love Songs Written About Other Celebrities

At the end of the day, nobody can truly know what goes on in a relationship except the two people involved — unless, of course, one of those individuals is a famous singer-songwriter. Over the years, plenty of fan-favorite artists, including Taylor SwiftHarry Styles, and Miley Cyrus, have used their love lives as inspiration.

In fact, Taylor, who began her career in 2006, is known for singing about her relationships. Nowadays, the Grammy winner is happily dating boyfriend Joe Alwyn. However, prior to the pair’s romance, Taylor released hit breakup track after hit breakup track. Take “We Are Never Ever Getting Back Together,” for example.

The 2012 hit single off her fourth studio album, Red, is the sort of empowering single that transcends generations. While the lyrics are fun and playful, the message is pretty strong. “I used to think that we were forever ever, ever / And I used to say, ‘never say never’/ Ah, so he calls me up and he’s like, ‘I still love you’/ And I’m like, I’m just, I mean this is exhausting, you know?/ Like we are never getting back together, like, ever,” Taylor sings.

So, which one of Taylor’s famous exes was the song written for? “It’s definitely about Jake,” a source told Us Weekly in 2012, referring to her ex-boyfriend Jake Gyllenhaal. The Donnie Darko actor and the Pennsylvania native dated for three months before ultimately calling it quits in December 2010. Over 10 years later, Taylor rereleased her hit songs (owned by Big Machine Records), sparking some unwanted attention toward Jake and Taylor’s other ex, John Mayer, whom she briefly dated between 2009 and 2010. 

Taylor has such a ~big reputation~ for writing about her love life that fans have come to expect it. Question is, how do her exes feel? “We always say we write from personal experience and I think everyone does so it would be hypocritical of us to be like ‘Oh, you can’t write songs’ and she’s really good, so they’re really good songs. So, I’m lucky in that sense,” Harry, who Taylor dated from late 2012 to early 2013, told Rolling Stone in 2017.

“That’s part of being a musician, I guess. You write songs about each other,” Joe Jonas, who dated Taylor in 2008, said in a May 2015 interview. “She’s great. Yeah, we’re friends. In this industry you meet a lot of people and you stay in touch. Obviously, it’s tough to be friends with people that are always constantly traveling, but yeah, we’re cool.”

However, John wasn’t too thrilled about the pop icon rereleasing her music, especially as he faced backlash a decade after her single “Dear John” from Speak Now dropped.

“John is trying his best to avoid the attention he’s been getting from Taylor’s new album,” a source told Us Weekly in November 2021. “[He] hasn’t spoken to [Taylor] in forever, so he learns about her feelings through her music.” 

Taylor has yet to rerelease Speak Now (Taylor’s Version).

Scroll through the gallery below to see love songs written about other celebrities.