Inside Taylor Swift’s rocky past romances including drama with John Mayer and Joe Jonas as she gets engaged to Joe Alwyn
TAYLOR Swift has a long list of ex-lovers and some of those relationships went down in flames.
However, the All Too Well singer has found her end game and is reportedly engaged to her boyfriend of six years, Joe Alwyn, after keeping their romance private.
A pal of the Conversations With Friends actor told The Sun that the couple is secretly engaged and have no plans to formally announce the happy news.
They went on to say that he bought Taylor a ring that she “wears behind closed doors.”
They also said that the couple told their inner circle, but not some members of their team.
Joe’s friend continued, “Taylor and Joe are incredibly happy and very, very in love.”
“They’ve actually been engaged for a few months but have only told their inner-inner circle — basically immediate family, and trusted, very old friends. Everyone has been sworn to secrecy, too.”
They continued, “Taylor has a beautiful ring but she only wears it when she’s at home — ie behind closed doors. Again, only a handful of people know details about the wedding and Taylor hasn’t even told some of her team about the engagement.
“They want their love to stay away from the cameras as much as possible. This is just for them. And if and when they do exchange vows, there most definitely won’t be any Vogue, Rolling Stone, or Hello! magazines there. It will be simple and elegant — like them.”
There are no specific details of the wedding yet and it is not known if the couple will officially confirm the news.
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The rumors of the engagement come about six years after the couple started dating when they first met at the Met Gala.
However, before Taylor “said yes,” she has had a string of men she has been romantically linked to, including famous and non-famous ones.
Here’s how those relationships went down.
BEFORE FAME
Taylor rose to fame at the age of 16 when she released her debut, self-titled album in 2006.
Even back then she was singing about boys who broke her heart, but they weren’t anyone the general public knew.
They were boys from her school and personal life that she had crushes on or dated.
Some of the boys that weren’t famous that Taylor dated include Brandon Borello, who inspired her debut single, Tim McGraw, and the song Fifteen.
Their relationship ended because he went off to college and she was only a freshman when he was a senior.
She then wrote Picture to Burn about Jordan Alford, whom she called a “redneck heartbreak who’s really bad at lying.”
Her famous hit, Teardrops on My Guitar was about a boy named Drew Hardwick, who she had a crush on but never really dated.
After he heard the song, he showed up at her house and asked her out, but she declined.
Her last boyfriend before fame was Sam Armstrong.
He inspired the song, Should’ve Said No after he cheated on her shortly before her first album came out.
JOE JONAS
By the time her sophomore album, Fearless, came out, Taylor’s fame and love life were thrown into the spotlight.
Her first public relationship was with Jonas Brothers member and actor, Joe Jonas, from July to October 2008.
Joe inspired many songs on Fearless and her third album, Speak Now, including Forever & Always, Last Kiss, Jump Than Fall, and the vault track, Mr. Perfectly Fine.
Their relationship came at the height of the Jonas Brothers mania, which made it really hard for the couple to go out together and not be bombarded by fans.
Even though they only dated for a few months, their relationship and the break-up were filled with drama as he dumped her over a 27-second phone call.
She blasted him on The Ellen DeGeneres Show and in her SNL monologue, but the singers appear to be on good terms now.
They have both moved on, Joe is currently married to Game of Thrones actress, Sophie Turner, and she even sent him a present for his baby.
In the song, invisible string off her seventh studio album, folklore, she sings, “Cold was the steel of my ax to grind For the boys who broke my heart. Now I send their babies presents.”
The exes seem to be so cool with each other that even Joe changed some lyrics to his song.
This was right around the time, they were expecting their first child together, Willa.
While the JoBros performed at their Las Vegas residency, they performed some deep cuts that they haven’t sung in years.
The song, Much Better, which is featured on their album, Lines, Vines, and Trying Times reads, “Now I’m done with superstars and all the tears on her guitar.”
Many fans took that to be about Taylor since she has a song with the same title.
However, during their residency, he sang the song again and changed the lyrics to, “Now I’m cool with superstars.”
LUCAS TILL
Taylor met actor Lucas Till on the set of the Hannah Montana Movie, which she wrote many songs for.
He appeared in Taylor’s music video, You Belong With Me, and played her love interest.
They apparently dated for a few months in 2009 but decided they were better off as friends.
Lucas told MTV later that year, “We dated for a little bit. But there was no friction because we were too nice. We just really both liked each other…[but] most relationships work out ’cause you get along and then you don’t, and then you makeup 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.”
No songs are rumored to be about him.
TAYLOR LAUTNER
In the latter part of 2009, Taylor began dating Twilight actor, Taylor Lautner, after they met on the set of Valentine’s Day where they played boyfriend and girlfriend.
According to MTV, he was more into her than she was with him and he went everywhere he could to see her, but the relationship just did not work out.
They broke up in early 2010 and she penned the apology song, Back to December, about him.
She seemed to regret the break-up as she sang, “You gave me all your love and all I gave you was goodbye.”
At the end of the song, Taylor begged to get him back, but the couple never reunited.
In a 2016 interview with his Scream Queens co-stars, Lea Michele asked him how felt to have a song written about him.
He told her that he finds the prospect “hilarious” and that writing songs about people is “what she does.”
It is unclear if the two have made up or not, but they do not appear to be enemies.
JOHN MAYER
In December 2009, Taylor moved on from the actor and began dating singer John Mayer.
Their relationship only lasted a few months, but their break-up was messy and is remembered as one of her most memorable relationships.
She wrote the heartwrenching track 5, Dear John, about him, as well as I Knew You Were Trouble from her fourth album, RED, and a few others from Speak Now.
The pair began dating after they collaborated on the song, Half of My Heart together.
The songs written about him implied that she had been warned about dating John and that he played games with her heart.
Their age difference also played a factor in why they split- she was 19 and he was 32 at the time.
The couple broke up in early 2010 and have had bad blood ever since.
He did not like that she wrote a song about him without telling him.
John told Rolling Stone in 2012, “I never got an email. I never got a phone call. I was really caught off guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if, at the lowest you’ve ever been, someone kicked you even lower?”
“I will say as a songwriter that I think it’s kind of cheap songwriting. I know she’s the biggest thing in the world, and I’m not trying to sink anybody’s ship, but I think it’s abusing your talent to rub your hands together and go, ‘Wait till he gets a load of this!’ That’s bulls**t.”
He was also partially responsible for the feud between Taylor and Katy Perry, as he went on to date Katy after her.
She then went on to date Cory Montieth for less than a month and wrote the song Mine about him.
JAKE GYLLENHAAL
If you know anyone Taylor has dated, you probably remember her relationship with Jake Gyllenhaal all too well.
The couple broke the internet when they were photographed drinking maple lattes and walking down the street with their arms around each other.
Us Weekly first broke the news of the couple dating in October 2010 by posting the picture on their front cover.
The relationship seemed to be going well- Jake even paid for her to fly on a $160k jet for a date.
However, things took a turn for the worse when Taylor was, once again, broken up with over text in January 2011.
She was blindsided by the breakup and claimed that it came “out of the blue.”
The songs We Are Never Ever Getting Back Together, I Almost Do, State of Grace, The Moment I Knew, and the infamous All Too Well are all supposedly about Jake.
When Taylor released her rerecord version of RED, more songs, including I Bet You Think About Me, Better Man, Babe, and the ten-minute version of All Too Well, were rumored to be about him.
Age played a big factor in their relationship- she was 19 and he was 28 when they first started dating.
They broke up when Taylor was 20 and Jake was 29.
In All Too Well (10-Minute Version), she sings, “And I was never good at telling jokes, but the punchline goes, I’ll get older, but your lovers stay my age,” taking a jab at how he continues to date younger women.
She even went on to detail the toxicity of their relationship in All Too Well: The Short Film.
They also split up due to the amount of press their relationship was getting.
The exes do not seem to be on good terms, as he received hate on the internet after fans found out more details of their relationship.
Jake seemed to be unbothered by the rerelease however, but still supposedly has Taylor’s old scarf.
CONNOR KENNEDY
Taylor took some time to heal, and write an album about Jake, before she got into another relationship.
In July 2012, she was photographed with Connor Kennedy, the son of Robert F. Kennedy Jr., in July 2012.
Us Weekly broke the news that the two were dating when they were seen in Hyannisport, Massachusetts together.
An onlooker revealed that “Connor put his arm around Taylor and they kissed behind the boat shed.”
Although they only dated until October of that year, the split was “totally amicable” and they broke up because of distance, according to E!.
The song, Begin Again, is rumored to be about him and Starlight supposedly recounts his grandparents, Robert and Ethel Kennedy’s relationship.
HARRY STYLES
Taylor moved on quickly from Connor when she started dating Harry Styles one month after their break-up.
She and the One Direction member dated for only three months, from November 2012 to January 2013, but their relationship is still one of the most talked-about in the fandom.
A lot happened in those 90 days.
The couple “went public” in December 2012 when they were photographed strolling around the Central Park Zoo.
Haylor, as the fans called them, seemed very comfortable with each other as they walked arm in arm.
They met backstage at the 2012 Kid’s Choice Awards and seemed to hit it off, but they didn’t date until the end of the year.
During their short-lived fling, fans thought Taylor and Harry were involved in a crash together, which inspired the bridge for her single, Out of the Woods- “Remember when you hit the brakes too soon? Twenty stitches in a hospital room. When you started crying, baby, I did too, But when the sun came up, I was looking at you.”
Taylor later revealed it was about an actual snow-mobile accident that took place with an ex and she “saw her life flash before her eyes.”
She later told Rolling Stone that Out of the Woods was about how, in her last high-profile relationship, “every day was a struggle. Forget making plans for life – we were just trying to make it to next week.”
The chorus of the song is all about her anxiety regarding the relationship.
Apparently, the couple’s relationship started to crack when they were on vacation together and had a huge fight, after spending Christmas apart.
They spent New Year’s together in the British Virgin Islands and Taylor reportedly left early after their blow-up and flew back to the US.
She even dissed the singer at the 2013 Grammys when she performed We Are Never Ever Getting Back Together and used a British accent in the performance.
Most of her 1989 album is about the British singer including the hits Style, I Know Places, and All You Had To Do Was Stay.
He followed up with the One Direction single, Perfect, which talks about looking for someone “to write their break-up songs about.”
Harry’s solo song, Two Ghosts is also rumored to be about Taylor.
Two years after their relationship ended, Taylor hosted a Billboard Awards after-party and all of the One Direction members were present, except for Harry.
However, despite everything they went through, the singers seem to get along just fine now.
At the 2021 Grammy Awards, Taylor was the first person to stand up and clap when Harry won his first Grammy for Best Pop Solo Performance for his smash hit, Watermelon Sugar.
They even shared a friendly moment right before a commercial break where they hugged and chatted for a bit before going their separate ways.
CALVIN HARRIS
Taylor was single for almost two years before she met DJ Calvin Harris in February 2015.
They met at an Elle Style Awards party and a month later, they sported matching outfits while shopping at Whole Foods.
Calvin and Taylor went public with their relationship at the 2015 Billboard Music Awards.
They kissed and hugged for the camera after Taylor won an award.
The couple dated for over a year– until May 2016, when Calvin broke things off.
He accused Taylor of cheating on him, with Tom Hiddleston, in his song Ole.
Calvin publicly tweeted about their break-up and Taylor retweeted his tweet, which read, “The only truth here is that a relationship came to an end, and what remains is a huge amount of love and respect.”
Despite being one of Taylor’s longer relationships, she did not write any songs about the DJ, after he made her promise not to.
He forgot to thank her in his 2016 GQ Men of the Year speech, which was later referenced in her song, coney island- “But when I walked up to the podium, I think that I forgot to say your name.”
They had a pretty public relationship and posted many pictures of each other on Instagram, but deleted them after they broke up.
TOM HIDDLESTON
The Summer of 2016 was filled with pictures of Tom Hiddleston and Taylor together.
Not long after she and Calvin broke up that May, she and the Marvel actor got together.
They met at The Met Gala and were seen kissing in Rhode Island a month later.
He met her parents in Nashville, they went to a Selena Gomez concert together, and Tom wore the famous “I HEART TS” shirt while in the ocean with Taylor and friends.
However, in September 2016, things went south when Taylor was worried Tom wasn’t with her for the right reasons.
He wanted to be very public with their romance while she preferred to keep things private.
They ended things a few days later.
The song Getaway Car is about her relationship with Tom and how Joe Alwyn got her away from that relationship.
JOE ALWYN
Once again, The Met Gala sparked a relationship for Taylor.
Back when the cardigan singer was deemed “Bleachella” with her bleach-blonde hair, she met Joe Alwyn on the red carpet in 2016.
The couple kept their relationship very private, but The Sun confirmed they were dating a year later in May 2017.
Joe and Taylor mostly keep out of the spotlight by staying in London and not talking about their relationship much.
In December 2017, they were seen at an Ed Sheeran concert together.
And Joe attended most of Taylor’s tour dates on the reputation Stadium Tour in 2018.
In September 2018, they were spotted together at the premiere of Joe’s movie The Favourite.
And in 2019, they were photographed getting cozy at the BAFTAs.
Joe even posted a photo of Taylor’s cat, Benjamin, in 2020, on his Instagram.
The couple wrote many songs together for her albums, folklore, and evermore while in quarantine, but Joe used a fake name, William Bowery, to cover it up.
Read More On The Sun
Now, six years later, Taylor has written many songs about him, spanning four albums.
Joe is the longest relationship Taylor has had.
