Taylor Swift’s rehearsal dinner is reportedly happening tonight at Madison Square Garden, with the wedding itself expected tomorrow, July 3. Before Swifties spiral fully into wedding mode, it’s worth revisiting the long, thoroughly documented road that got her here.
Almost none of Taylor’s relationships stayed private, and most of them ended up as albums. So on the eve of the wedding of the decade, here’s a detailed rundown of every boyfriend who came before Travis Kelce, and the songs they may have inspired along the way.
The High School And Early Fame Years
Taylor’s first widely reported relationship was with Joe Jonas in 2008. The two dated for about three months while Jonas was still riding high with the Jonas Brothers, and their breakup became the stuff of pop culture legend when Taylor told Ellen DeGeneres that Jonas ended things over a phone call that lasted just 25 seconds. She turned around and booked a last-minute studio session to record “Forever & Always” almost immediately after.
Not long after, Taylor had a brief romance with Taylor Lautner that began on the set of the ensemble film “Valentine’s Day.” The two reportedly stayed close after splitting, and fans have long pointed to “Back to December” as her apology to him. Around the same period, Taylor was linked to actor Lucas Till, though little was ever confirmed about that pairing beyond speculation.
Dear John, All Too Well, And Begin Again
Taylor’s relationship with John Mayer, which unfolded around 2009 and 2010, drew significant attention because of their 13-year age gap. She was 19, and he was 32, and the fallout produced one of her most direct breakup songs, “Dear John,” which many fans read as an accusation of manipulation aimed squarely at Mayer.
From there, Taylor dated actor Jake Gyllenhaal from October 2010 to January 2011. The relationship was short but is widely credited as the inspiration behind “All Too Well” and its extended ten-minute version, both of which reference a scarf left behind at a family member’s house and an age gap between the two.
In 2012, Taylor was briefly linked to Conor Kennedy, grandson of the late Robert F. Kennedy. She reportedly bought a home near the Kennedy family compound in Hyannis Port while they dated, and the relationship, though short, is believed to have inspired “Begin Again” on the album “Red.”
Style, Getaway Car, And The Road To Kelce
Taylor’s romance with Harry Styles ran from 2012 into 2013, and fans have spent over a decade decoding songs that may reference him, most notably “Style” off “1989.” The 2023 re-release of that album included the vault track “Is It Over Now?”, which added new lyrical detail widely interpreted as being about their relationship.
Her relationship with Calvin Harris began in February 2015 after Ellie Goulding introduced the two at the Elle Style Awards. They made things public with a kiss at the Billboard Music Awards in May 2015, celebrated their first anniversary in 2016, and split just two months later. Songs like “Getaway Car” are widely believed to reference the tail end of that relationship.
Weeks after the Harris split, Taylor was linked to actor Tom Hiddleston, whom she met at the 2016 Met Gala. Their romance moved fast, with the pair spotted in Rhode Island, Rome, London, and Australia over about 3 months, earning them the nickname “Hiddleswift.” Hiddleston famously wore an “I heart T.S.” tank top at her Fourth of July party before the two split that September.
Then came the relationship that shaped an era. Taylor and actor Joe Alwyn dated for roughly six years, staying together through the pandemic, before splitting in the spring of 2023. Much of “Folklore,” “Evermore,” and later “The Tortured Poets Department” is believed to draw from their time together. A brief, rumored fling with The 1975’s Matty Healy surfaced in the immediate aftermath of that breakup.
Then, in July 2023, Kansas City Chiefs tight end Travis Kelce attended her Eras Tour show at Arrowhead Stadium and later revealed on his podcast that he’d tried and failed to hand her a friendship bracelet with his number on it. Two years, one Super Bowl run, and one viral engagement announcement later, all signs point to the two saying “I do” at Madison Square Garden this Friday.
After a dating history that spanned a decade and a half of albums, Taylor’s happy ending is finally arriving in real time.
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