September 22, 2023
We thought… If all of Taylor Swift’s ex‑boyfriends chose an engagement ring for her, what would they have picked? Here’s our answer based on each guy’s personality, the songs Taylor wrote about them, and the trends of the time they were dating!
Let's kick things off with none other than Mr. Perfectly Fine himself, Joe Jonas. Their whirlwind romance, which ignited in July and fizzled out by October of 2008, left quite the mark in celebrity dating history. Notably, Jonas chose to end things in a rather abrupt breakup over the phone, which Swift confirmed in an interview on Ellen.
If Joe and Taylor's love story had evolved into something that was 'Forever & Always,' we can imagine him selecting our simple and classic signature Bloom Collection solitaire setting, Azalea, with a pear shaped diamond- a choice that echoes the timeless love young Taylor dreamt of having.
Next on our list is Lucas Till. Now, you might be scratching your head and wondering, "Lucas who?" Let's jog your memory a bit—he made a cameo in Taylor's "You Belong with Me" and played the charming cowboy in "Hannah Montana: The Movie." If the name still doesn't ring a bell, don't worry; their romance in 2009 was more of a brief interlude than a headline-grabbing affair.
But let's entertain the thought for a moment: if their connection had blossomed into something more, we could picture Lucas selecting an engagement ring with a touch of vintage charm. We chose our signature Bloom Collection setting, Paisley, with an Old Mine Cut Diamond center.
Taylor dated Taylor Lautner in Fall of 2009 while filming the iconic rom-com Valentine’s Day. Lautner recently appeared in Swift’s new music video for “I Can See You” and is a fan favorite among her exes.
We think the Twilight star would have chosen our signature Bloom Collection setting, Petunia, with a cushion center diamond. We selected this ring because it was a popular style back in 2009. We think of him as a trendy guy because if you take a glance at his wife’s (oddly, also named Taylor), you'll notice that he opted for an oval solitaire, which happens to be a trendy choice today.
Up next, we have John Mayer. They began dating when Taylor was only nineteen and John was thirty-two–we’ll just leave that there for you… It’s pretty easy to determine which song was written about him considering his name is in the title.
For Mayer, we chose a ring that is just as flashy as he is, our Round Diamond Floral Halo.
Our next featured ex is one we all know "All Too Well"... Jake Gyllenhaal. Taylor dated Jake shortly between 2010 and 2011. We won't dwell on him for too long, because Taylor has already dedicated a full 10 minutes belting out her emotions about it.
Anyways, if they had made it to the altar (which we’re glad they didn’t) we think Jake would’ve chosen Dahlia, from our signature Bloom Collection, with a round diamond center. Moving on!
Taylor’s history with Robert F. Kennedy's grandson, Conor, nearly granted her the title of a Kennedy. Their fleeting romance, which spanned just two months, left fans curious about what might have been.
In a hypothetical engagement scenario, we envision Conor selecting a breathtaking 2.5-carat emerald in our signature Bloom Collection setting, Azalea- timeless and elegant (and BIG…I mean he is a Kennedy!).
Taylor Swift and Harry Styles' relationship was a high-profile relationship that captured the attention of fans and the media in 2012. The two briefly came together and inspired songs on both sides, with Taylor's "Style" and Harry's "Two Ghosts" often speculated to be about their relationship.
While their love story was brief, it remains a noteworthy chapter in Taylor’s dating history. Given Harry’s unique style, we think he would have chosen a ring with a bit of individuality to it, that’s why we chose our marquise diamond with a wide bezel setting!
One of Taylor’s longest lasting relationships was with famous DJ, Calvin Harris. The pair were together from February 2015 to May 2016. Apparently Harris broke things off in what sources described as a “brutal” split.
Considering these two were pretty serious, we believe the Scottish DJ would have spoiled Swift with our gorgeous baguette step cut diamond graduating bezel ring had things not gone south for the couple.
Tom Hiddleston stepped into Taylor’s life in May 2016. The two lasted until September of the same year. Their relationship was far from low-key, marked by public appearances at the Met Gala and Selena Gomez's concert. Hiddleston even made headlines wearing an 'I heart TS' shirt.
Imagining a potential engagement with Tom, we can see him choosing our Old Mine Cut Diamond Antique Ring with a Emerald Gemstone Halo, playfully nodding to his Marvel character, Loki.
As we approach the end of Taylor's dating chronicles, we can't help but reflect on her most recent relationship with Joe Alwyn. Taylor and Joe initially kept their romance under wraps before stepping into the public eye at an Ed Sheeran concert in 2017. Sadly, their love story reached its conclusion in April of this year.
Yet, in the world of what-ifs, we believe that had their love endured, Joe might have chosen a remarkable 3.5-carat oval diamond, set in our signature Bloom Collection setting, Iris.
As we wrap up this journey through Taylor Swift's romantic history, it's clear that her love life has been quite the rollercoaster. While the idea of engagement rings is a fun thought, what truly stands out is Taylor's ability to turn her life experiences into relatable songs that connect with fans around the world! We're excited to see where her love life takes her next, and her actual engagement ring when it's time!
