The Taylor Swift Boyfriends You Love, And The Ones You Didn't Know She Dated – Brit + Co

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Chloe Williams serves as B+C’s Assistant Editor, entertainment lead, and resident Taylor Swift expert. Whether she’s writing a movie review or interviewing the stars of the latest hit show, Chloe loves exploring why stories inspire us. You can see her work published in BuzzFeed, Coastal Review, and North Beach Sun. When she’s not writing, Chloe’s probably watching a Marvel movie with a cherry coke or texting her sister about the latest celebrity news. Say hi at @thechloewilliams on Insta and @popculturechlo on Twitter!
Taylor Swift is known for many things: her incredible songwriting, record-breaking albums like 1989, Folklore, and Midnights, and the Easter eggs she's always leaving fans for her new albums. But the popstar is also known for her relationships (friendly reminder, women are more than their partners!). Considering there's a Taylor Swift song for every kind of love, heartbreak, and relationship, here's everything you need to know about Taylor Swift's former boyfriends (and her current romance with Kansas City Chiefs player Travis Kelce), from a Swiftie who's done the research.

Photo by JB Lacroix/Getty Images

Lucas Till

I've said it once and I'll say it again: Hannah Montana: The Movie is one of the greatest films of the 2000's, and this is just another reason why. The feature film stars Lucas as Miley/Hannah's love interest Travis (who we never saw again after the movie??), while Taylor performs "Crazier" during the characters' barn party.

Taylor Swift ended up featuring Lucas Till as the male lead in her "You Belong With Me" music video, which won her the VMA for Best Video by a Female Artist in 2009.

"We dated for a little bit. But, there was no friction because we were too nice," Taylor Swift's boyfriend told MTV in 2009. "Most relationships work out cause you get along and then you don't, and then you make up and it's passionate, and with us I really just liked her as a friend. That’s the only reason that didn't work out."

Relive the romance: Taylor Swift hasn't released any songs about Lucas Till, but feel free to watch the "You Belong With Me" music video as many times as you'd like. I know I do.

Photo by Jamie McCarthy/Getty Images

Taylor Lautner

Taylor Swift and Taylor Lautner dated for a few months in 2009 after they met on the set of the rom-comValentine's Day. Taylor Lautner presented Swift with the VMA for Best Video by a Female Artist in 2009, which went down in pop culture history when Kanye jumped onstage to interrupt Swift's acceptance speech.

“I’m just assuming that this whole thing was a practiced and rehearsed skit because why else would Kanye West be jumping up on the stage interrupting Taylor Swift?" the Twilight star said on a recent episode of his The Squeeze podcast. "It just didn’t make sense. And if you look back at it, I’m actually caught, like, laughing and giggling at him like, ‘I can’t hear them but this is probably really funny right now.’”

The two have become friends since the end of their relationship, and most recently, Taylor Lautner starred with Joey King in the music video for Taylor Swift's "I Can See You" from Speak Now (Taylor's Version). "He was a very positive force in my life when I was making the Speak Now album," Taylor Swift said at the July 7 Eras Tour show.

Relive the romance: "Back To December"

Photo by Dimitrios Kambouris/Getty Images for VEVO

John Mayer

Even though Taylor Swift and John Mayer never publicly confirmed that they were dating, this has become one of Taylor's best-known relationships. The two collaborated on John's "Half of My Heart" single in 2009 before performing together a number of times before their relationship ended in 2010.

Taylor later released Speak Now, whose track "Dear John" is believed to be about the relationship. John also released a song that's widely thought to be about Taylor titled "Paper Doll," and spoke very candidly about the release + reception of "Dear John" in a 2012 interview with Rolling Stone.

“It made me feel terrible,” he says. “Because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do.”

Relive the romance: "Dear John," "Would've, Should've, Could've"

Photo by Larry Busacca/Getty Images for NARAS

Cory Monteith

While the late Glee star never publicly became one of Taylor Swift's boyfriends, the pair was photographed together on a few different occasions and fans have speculated since the release of Speak Now that the album's lead single "Mine" is about the actor.

"This is a situation where a guy that I just barely knew put his arm around me by the water, and I saw the entire relationship flash before my eyes, almost like a weird science-fiction movie," she told Yahoo Music, via MTV.

After the actor passed away, Taylor Swift tweeted (via Taste of Country, the tweet has since been deleted), "Speechless. And for the worst reason."

Relive the romance: "Mine"

Photo by Imeh Akpanudosen/Getty Images

Adam Young

Okay, so Adam Young and Taylor Swift never *officially* dated, but they did send each other emails and eventually meet face-to-face — a meeting that Taylor was so excited about, she ended up writing "Enchanted," which Adam later covered.

Relive the romance: "Enchanted"

Photo by Alberto E. Rodriguez/Getty Images for Disney

Jake Gyllenhaal

One of Taylor Swift's most public relationships came in 2010 when she started dating movie star Jake Gyllenhaal. Throughout that fall, Taylor and Jake were seen grabbing brunch in New York City, spending Thanksgiving together, and visiting Nashville.

When December rolled around, Taylor celebrated her 21st birthday without Jake present, and a few days later, Jake celebrated his 30th birthday without Taylor. Their relationship ended shortly after, and Taylor released her album Red in 2012. The album is believed to be mostly about her relationship with Jake, and is filled to the *brim* with insight into her relationship (it also happens to be the perfect early fall album!)

Red also features her most beloved song "All Too Well," and in 2021, Taylor Swift released Red (Taylor's Version), which includes a 10-minute version of the song fans have been requesting for a decade, as well as a short film.

Relive the romance: "Red," "All Too Well," "The Moment I Knew," "I Bet You Think About Me"

Photo by Amy Sussman/Getty Images

Harry Styles

Rumors about Taylor Swift and Harry Styles being a couple when Harry showed up to support Taylor during her X Factor performance rehearsal. They began having dates in Central Park, attending parties together, and wore matching paper airplane necklaces. They even went on a skiing trip (a trip that many fans believe included a snowmobile accident, which Taylor mentions in 1989's "Out Of The Woods").

"In writing songs about stuff like [relationships], I like tipping a hat to the time together," Harry Styles said during a year-long Rolling Stone interview. "You're celebrating the fact it was powerful and made you feel something, rather than 'this didn't work out, and that's bad.' And if you run into that person, maybe it's awkward, maybe you have to get drunk … but you shared something. Meeting someone new, sharing those experiences, it's the best s— ever."

The exes almost broke Twitter when they reunited at the 2021 Grammys (among other awards, Taylor won Best Album for Folklore and Harry won Best Pop Solo Performance for "Watermelon Sugar"), and again at the 2023 Grammys. Here's hoping Harry Styles is featured on 1989 (Taylor's Version)!

Relive the romance: "Style," "Out Of The Woods," "Clean," "Question…?"

Photo by Joe Maher/Getty Images

Calvin Harris

Taylor Swift and Calvin Harris were introduced by their mutual friend Ellie Goulding, and appeared on lots of different red carpets together, as well as in a variety of Instagram posts. They also collaborated on "This Is What You Came For," which was recorded by Rihanna.

When the pair broke up, Calvin ended up posting some tweets (which have since been deleted), saying "I figure if you're happy in your new relationship you should focus on that instead of trying to tear your ex bf down for something to do." Afterwards, he told British GQ, via People that "it was completely the wrong instinct…It's very difficult when something I consider so personal plays out very publicly. The aftermath of the relationship was way more heavily publicized than the relationship itself."

Relive the romance: "I Forgot That You Existed," "Bejeweled," "High Infidelity"

Photo by Tristan Fewings/Getty Images

Tom Hiddleston

Right after Taylor Swift and Calvin Harris broke up, the popstar was linked to the English actor at the 2016 Met Gala. The couple then proceeded to send the internet into a tizzy when they were photographed holding hands and cuddling in Rhode Island. They introduced one another to their parents, attended concerts together, and traveled to places like Rome and Australia. They ended up breaking things off in September of 2017.

Relive the romance: "Getaway Car"

Photo by Mike Coppola/Getty Images for The Gotham Film & Media Institute

Joe Alwyn

The longest relationship between Taylor Swift and a boyfriend is rumored to have begun at the 2016 Met Gala (the song "Dress" mentions she met the song's subject when she had bleached hair and they had a buzzcut. Taylor had bleached hair and Joe had a buzzcut at the Gala that year), but were officially connected in 2017. They traveled around the world together, and Joe showed up to support Taylor Swift's Reputation tour.

The couple's early relationship began during a period where a lot of the public and the industry expressed that they were anti-Taylor Swift, and the singer basically disappeared. Taylor told The Guardian in 2019 that they preferred to keep things private, otherwise "people think it's up for discussion, and our relationship isn't up for discussion…If you and I were having a glass of wine right now, we'd be talking about it — but it's just that it goes out into the world."

While many fans speculated that Taylor Swift and Joe Alwyn had gotten engaged, after six years of dating, the couple's split became publicized in the spring of 2023. But on November 29, Taylor's friend and collaborator Jack Antonoff posted an Instagram story confirming Taylor's hit song "You're Losing Me" was written in 2021. "A very special track from the Midnights vault that's finally streaming," the story says. "Written and recorded at home on 12/5/21."

That makes us look at a lot of the heart-wrenching songs on Evermore and Midnights in a whole new way because it suggests their relationships problems ran deeper and lasted longer than anyone realized. And on November 30, Taylor Swift's publicist Tree Paine made an ultra-rare statement on Taylor Swift and Joe Alwyn's relationship after the infamous gossip blog Deuxmoi published an Instagram story claiming Taylor and Joe got married.

"Enough is enough with these fabricated lies about Taylor from Deuxmoi," Tree says on X. "There was NEVER a marriage or ceremony of ANY kind. This is an insane thing to post. It’s time for you to be held accountable for the pain and trauma you cause with posts like these."

Taylor announced her new album, The Tortured Poets Department, at the 2024 Grammys…and then internet was QUICK to make potential connections to Joe. In 2022, Joe told GQ that he was in a group chat with Paul Mescal and Andrew Scott called "The Tortured Man Club," based on their roles in their respective film and TV projects. Taylor also has tracks like "So Long, London" which in direct juxtaposition to "London Boy" off her Lover album — a song heavily tied to Joe. The through line is more than clear, TBH, but tricksy could be misleading us.

Regardless, a "source close to Joe" spoke up about the album to The Daily Mail. The source said that Joe has been quiet and respectful about the breakup, so it would be "shady" to "diss" him in the album. What does Taylor think about that? Well, during a performance "Dear Reader" in Tokyo — notably after Joe's alleged comments — she sang, "The restless tears of a cursed man." The original lyrics? "The desperate prayers of a cursed man." Now, I'm not saying she was calling Joe a crybaby…but I'm not NOT saying it. 😗

Relive the romance: "Delicate," "Lover," "Paper Rings," "Invisible String," "Snow on the Beach" (basically all of Reputation, Lover, Folklore, Evermore, and a good deal of Midnights).

Photo by Marcelo Hernandez/Getty Images

Matty Healy

During the summer leg of the Eras Tour, Taylor Swift and Matty Healy both mouthed the words “This is about you. You know who you are. I love you.” into the camera during their respective shows. They were later spotted together in New York City, and Matty joined boygenius onstage to open for one of Taylor's concerts in Nashville. However, the pair ended things at the beginning of June.

"They were never boyfriend-girlfriend or exclusive and were always just having fun," a source tells People. "There is no drama, and who knows what could happen again. It was a good time and ran its course."

Photo by JC Olivera/Getty Images
“Taylor and Travis have been quietly hanging out,” a source told The Messenger in September, while a source told ET that "Travis has been into Taylor for a while and definitely has a crush on her." However, another insider confirms that the pair aren't officially dating, and on September 20, Travis' brother Jason Kelce told the WIP Morning Show (via DailyMail), "I think things are going great and I think it's 100 percent true."
On September 24, Taylor was seen in a box with Travis Kelce's mom during the Chiefs game, and then left with Travis Kelce after the game (in which Travis scored an impressive touchdown *and* the Chiefs won 41-10). Travis wore a blue and white matching set (that also has 1989 in the name 👀), while Taylor wore a white tank and an unreleased Chiefs jacket (via taylorswiftstyled). Speaking of clothes, it's also notable to mention that after Taylor was spotted at the game, sales for Travis' jersey have jumped 400%!
In a September 27 interview with the New Heights podcast, Travis talks about the game, and said he "sure as hell enjoyed this weekend."
"I just thought it was awesome how everybody in the suite had nothing but great things to say about her," he says. "She looked amazing and everybody was talking about her in great light."
After spending some time with his mom in the Kelce box, Taylor joined Travis and they "just slid off in the getaway car at the end." Is that a Reputation (Taylor's Version) Easter egg we hear? Swifties have been predicting the rerecording would come after 1989 (Taylor's Version) since the Midnights era (as for us, we're hoping to get an announcement this fall). Check back here to see how this potential relationship unfolds!
Photo by Emma McIntyre/Getty Images for SiriusXM
Taylor Swift and Joe Jonas began dating in 2008. Taylor joined the Jonas Brothers during their Burnin' Up Tour and performed hits like "Should've Said No." The relationship is most remembered for the fact that Joe reportedly broke up with Taylor during a 25-second phone call. After the break up (and a few albums), the couple was able to become friends.
Taylor Swift's "Invisible String" (which was released after Joe Jonas and Sophie Turner had their first baby) includes the line, "Cold was the steel of my axe to grind // For the boys who broke my heart // Now I send their babies presents," solidifying that the duo had truly buried the hatchet.
Relive the romance: "Forever & Always," "Mr. Perfectly Fine," "Last Kiss"
Photo by JB Lacroix/Getty Images
I've said it once and I'll say it again: Hannah Montana: The Movie is one of the greatest films of the 2000's, and this is just another reason why. The feature film stars Lucas as Miley/Hannah's love interest Travis (who we never saw again after the movie??), while Taylor performs "Crazier" during the characters' barn party.
Taylor Swift ended up featuring Lucas Till as the male lead in her "You Belong With Me" music video, which won her the VMA for Best Video by a Female Artist in 2009.
"We dated for a little bit. But, there was no friction because we were too nice," Taylor Swift's boyfriend told MTV in 2009. "Most relationships work out cause you get along and then you don't, and then you make up and it's passionate, and with us I really just liked her as a friend. That’s the only reason that didn't work out."
Relive the romance: Taylor Swift hasn't released any songs about Lucas Till, but feel free to watch the "You Belong With Me" music video as many times as you'd like. I know I do.
Photo by Jamie McCarthy/Getty Images
Taylor Swift and Taylor Lautner dated for a few months in 2009 after they met on the set of the rom-comValentine's Day. Taylor Lautner presented Swift with the VMA for Best Video by a Female Artist in 2009, which went down in pop culture history when Kanye jumped onstage to interrupt Swift's acceptance speech.
“I’m just assuming that this whole thing was a practiced and rehearsed skit because why else would Kanye West be jumping up on the stage interrupting Taylor Swift?" the Twilight star said on a recent episode of his The Squeeze podcast. "It just didn’t make sense. And if you look back at it, I’m actually caught, like, laughing and giggling at him like, ‘I can’t hear them but this is probably really funny right now.’”
The two have become friends since the end of their relationship, and most recently, Taylor Lautner starred with Joey King in the music video for Taylor Swift's "I Can See You" from Speak Now (Taylor's Version). "He was a very positive force in my life when I was making the Speak Now album," Taylor Swift said at the July 7 Eras Tour show.
Relive the romance: "Back To December"
Photo by Dimitrios Kambouris/Getty Images for VEVO
Even though Taylor Swift and John Mayer never publicly confirmed that they were dating, this has become one of Taylor's best-known relationships. The two collaborated on John's "Half of My Heart" single in 2009 before performing together a number of times before their relationship ended in 2010.
Taylor later released Speak Now, whose track "Dear John" is believed to be about the relationship. John also released a song that's widely thought to be about Taylor titled "Paper Doll," and spoke very candidly about the release + reception of "Dear John" in a 2012 interview with Rolling Stone.
“It made me feel terrible,” he says. “Because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do.”
Relive the romance: "Dear John," "Would've, Should've, Could've"
Photo by Larry Busacca/Getty Images for NARAS
While the late Glee star never publicly became one of Taylor Swift's boyfriends, the pair was photographed together on a few different occasions and fans have speculated since the release of Speak Now that the album's lead single "Mine" is about the actor.
"This is a situation where a guy that I just barely knew put his arm around me by the water, and I saw the entire relationship flash before my eyes, almost like a weird science-fiction movie," she told Yahoo Music, via MTV.

After the actor passed away, Taylor Swift tweeted (via Taste of Country, the tweet has since been deleted), "Speechless. And for the worst reason."
Relive the romance: "Mine"
Photo by Imeh Akpanudosen/Getty Images
Okay, so Adam Young and Taylor Swift never *officially* dated, but they did send each other emails and eventually meet face-to-face — a meeting that Taylor was so excited about, she ended up writing "Enchanted," which Adam later covered.
Relive the romance: "Enchanted"
Photo by Alberto E. Rodriguez/Getty Images for Disney
One of Taylor Swift's most public relationships came in 2010 when she started dating movie star Jake Gyllenhaal. Throughout that fall, Taylor and Jake were seen grabbing brunch in New York City, spending Thanksgiving together, and visiting Nashville.
When December rolled around, Taylor celebrated her 21st birthday without Jake present, and a few days later, Jake celebrated his 30th birthday without Taylor. Their relationship ended shortly after, and Taylor released her album Red in 2012. The album is believed to be mostly about her relationship with Jake, and is filled to the *brim* with insight into her relationship (it also happens to be the perfect early fall album!)
Red also features her most beloved song "All Too Well," and in 2021, Taylor Swift released Red (Taylor's Version), which includes a 10-minute version of the song fans have been requesting for a decade, as well as a short film.
Relive the romance: "Red," "All Too Well," "The Moment I Knew," "I Bet You Think About Me"
Photo by Amy Sussman/Getty Images
Rumors about Taylor Swift and Harry Styles being a couple when Harry showed up to support Taylor during her X Factor performance rehearsal. They began having dates in Central Park, attending parties together, and wore matching paper airplane necklaces. They even went on a skiing trip (a trip that many fans believe included a snowmobile accident, which Taylor mentions in 1989's "Out Of The Woods").
"In writing songs about stuff like [relationships], I like tipping a hat to the time together," Harry Styles said during a year-long Rolling Stone interview. "You're celebrating the fact it was powerful and made you feel something, rather than 'this didn't work out, and that's bad.' And if you run into that person, maybe it's awkward, maybe you have to get drunk … but you shared something. Meeting someone new, sharing those experiences, it's the best s— ever."
The exes almost broke Twitter when they reunited at the 2021 Grammys (among other awards, Taylor won Best Album for Folklore and Harry won Best Pop Solo Performance for "Watermelon Sugar"), and again at the 2023 Grammys. Here's hoping Harry Styles is featured on 1989 (Taylor's Version)!
Relive the romance: "Style," "Out Of The Woods," "Clean," "Question…?"
Photo by Joe Maher/Getty Images
Taylor Swift and Calvin Harris were introduced by their mutual friend Ellie Goulding, and appeared on lots of different red carpets together, as well as in a variety of Instagram posts. They also collaborated on "This Is What You Came For," which was recorded by Rihanna.
When the pair broke up, Calvin ended up posting some tweets (which have since been deleted), saying "I figure if you're happy in your new relationship you should focus on that instead of trying to tear your ex bf down for something to do." Afterwards, he told British GQ, via People that "it was completely the wrong instinct…It's very difficult when something I consider so personal plays out very publicly. The aftermath of the relationship was way more heavily publicized than the relationship itself."
Relive the romance: "I Forgot That You Existed," "Bejeweled," "High Infidelity"
Photo by Tristan Fewings/Getty Images
Right after Taylor Swift and Calvin Harris broke up, the popstar was linked to the English actor at the 2016 Met Gala. The couple then proceeded to send the internet into a tizzy when they were photographed holding hands and cuddling in Rhode Island. They introduced one another to their parents, attended concerts together, and traveled to places like Rome and Australia. They ended up breaking things off in September of 2017.
Relive the romance: "Getaway Car"
Photo by Mike Coppola/Getty Images for The Gotham Film & Media Institute
The longest relationship between Taylor Swift and a boyfriend is rumored to have begun at the 2016 Met Gala (the song "Dress" mentions she met the song's subject when she had bleached hair and they had a buzzcut. Taylor had bleached hair and Joe had a buzzcut at the Gala that year), but were officially connected in 2017. They traveled around the world together, and Joe showed up to support Taylor Swift's Reputation tour.
The couple's early relationship began during a period where a lot of the public and the industry expressed that they were anti-Taylor Swift, and the singer basically disappeared. Taylor told The Guardian in 2019 that they preferred to keep things private, otherwise "people think it's up for discussion, and our relationship isn't up for discussion…If you and I were having a glass of wine right now, we'd be talking about it — but it's just that it goes out into the world."
While many fans speculated that Taylor Swift and Joe Alwyn had gotten engaged, after six years of dating, the couple's split became publicized in the spring of 2023. But on November 29, Taylor's friend and collaborator Jack Antonoff posted an Instagram story confirming Taylor's hit song "You're Losing Me" was written in 2021. "A very special track from the Midnights vault that's finally streaming," the story says. "Written and recorded at home on 12/5/21."
That makes us look at a lot of the heart-wrenching songs on Evermore and Midnights in a whole new way because it suggests their relationships problems ran deeper and lasted longer than anyone realized. And on November 30, Taylor Swift's publicist Tree Paine made an ultra-rare statement on Taylor Swift and Joe Alwyn's relationship after the infamous gossip blog Deuxmoi published an Instagram story claiming Taylor and Joe got married.
"Enough is enough with these fabricated lies about Taylor from Deuxmoi," Tree says on X. "There was NEVER a marriage or ceremony of ANY kind. This is an insane thing to post. It’s time for you to be held accountable for the pain and trauma you cause with posts like these."
Taylor announced her new album, The Tortured Poets Department, at the 2024 Grammys…and then internet was QUICK to make potential connections to Joe. In 2022, Joe told GQ that he was in a group chat with Paul Mescal and Andrew Scott called "The Tortured Man Club," based on their roles in their respective film and TV projects. Taylor also has tracks like "So Long, London" which in direct juxtaposition to "London Boy" off her Lover album — a song heavily tied to Joe. The through line is more than clear, TBH, but tricksy could be misleading us.
Regardless, a "source close to Joe" spoke up about the album to The Daily Mail. The source said that Joe has been quiet and respectful about the breakup, so it would be "shady" to "diss" him in the album. What does Taylor think about that? Well, during a performance "Dear Reader" in Tokyo — notably after Joe's alleged comments — she sang, "The restless tears of a cursed man." The original lyrics? "The desperate prayers of a cursed man." Now, I'm not saying she was calling Joe a crybaby…but I'm not NOT saying it. 😗
Relive the romance: "Delicate," "Lover," "Paper Rings," "Invisible String," "Snow on the Beach" (basically all of Reputation, Lover, Folklore, Evermore, and a good deal of Midnights).
Photo by Marcelo Hernandez/Getty Images
During the summer leg of the Eras Tour, Taylor Swift and Matty Healy both mouthed the words “This is about you. You know who you are. I love you.” into the camera during their respective shows. They were later spotted together in New York City, and Matty joined boygenius onstage to open for one of Taylor's concerts in Nashville. However, the pair ended things at the beginning of June.
"They were never boyfriend-girlfriend or exclusive and were always just having fun," a source tells People. "There is no drama, and who knows what could happen again. It was a good time and ran its course."
Were any of Taylor Swift's boyfriends your celebrity crushes? Let us know in the comments!
Lead photo by Dimitrios Kambouris/Getty Images
Chloe Williams serves as B+C’s Assistant Editor, entertainment lead, and resident Taylor Swift expert. Whether she’s writing a movie review or interviewing the stars of the latest hit show, Chloe loves exploring why stories inspire us. You can see her work published in BuzzFeed, Coastal Review, and North Beach Sun. When she’s not writing, Chloe’s probably watching a Marvel movie with a cherry coke or texting her sister about the latest celebrity news. Say hi at @thechloewilliams on Insta and @popculturechlo on Twitter!
Chloe Williams serves as B+C’s Assistant Editor, entertainment lead, and resident Taylor Swift expert. Whether she’s writing a movie review or interviewing the stars of the latest hit show, Chloe loves exploring why stories inspire us. You can see her work published in BuzzFeed, Coastal Review, and North Beach Sun. When she’s not writing, Chloe’s probably watching a Marvel movie with a cherry coke or texting her sister about the latest celebrity news. Say hi at @thechloewilliams on Insta and @popculturechlo on Twitter!

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