From teenage crushes to a NFL star popping the question in a forest, Taylor Swift’s love life has been as dramatic, emotional, and headline-worthy as her music catalogue
Taylor Swift has always had fans hooked on her love life, from her early heartbreaks to her most recent fairytale engagement with NFL star Travis Kelce.
The pop star’s romantic story reads like the ultimate chart-topping playlist with her teenage relationships inspired hits like ‘Tim McGraw’ and ‘Teardrops on My Guitar’, while her first high-profile romance with Joe Jonas in 2008 led to the fiery anthem ‘Forever & Always’.
A brief fling with Taylor Lautner in 2009 inspired the heartstring-tugging ‘Back to December’, and her romance with John Mayer gave birth to the iconic ‘Dear John’.
As her fame skyrocketed, so did the media attention on her relationships. Her 2010 romance with Jake Gyllenhaal inspired the emotional powerhouse ‘All Too Well’, and her whirlwind 2012 relationship with Harry Styles produced ‘Style’ and ‘Out of the Woods’.
Swift’s high-profile flings with Calvin Harris and Tom Hiddleston kept tabloids buzzing, proving her love life was almost as newsworthy as her music.
Taylor’s brief but notable romance with Matty Healy, the 1995-born singer and son of Loose Women star Denise Welch, caught public attention in December 2014 after meeting at one of Healy’s concerts. Their relationship resurfaced in May 2023, shortly after Swift’s split from Joe Alwyn, who she dated from 2017 – 2023.
The pair collaborated on songs and managed to keep much of their relationship out of the public eye. Their amicable split in 2023 marked the end of a six-year love story, leaving Swift ready for a new chapter.
That new chapter came with Travis Kelce, the Kansas City Chiefs tight end. Their romance started after Kelce gushed about Swift on his podcast in July 2023, and the pair were first spotted together in September 2023 at a Chiefs game.
They made their red carpet debut in June 2025, and fans were ecstatic when the engagement was announced on August 26, 2025.
The couple shared a joint Instagram post showing Kelce on one knee in a romantic forest, presenting Swift with a stunning cushion-cut diamond ring.
She captioned the post: “Your English teacher and your gym teacher are getting married.”
The engagement ring, designed with jeweller Kindred Lubeck, is a vintage-inspired piece featuring an Old Mine Brilliant Cut diamond.
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