The truth about Taylor Swift’s relationship with Conor Kennedy

Grammy-winning country crooner-turned-pop star Taylor Swift is known just as much for her string of high-profile relationships as she is for her slew of smash hits and critical accolades. While she’s been labeled a serial dater for her tendency to bounce from one Hollywood hunk to the next, many believe Swift may have finally found lasting love with longtime boyfriend Joe Alwyn, whom she’s been dating since May 2017.

In March 2020, a source close to the loved-up duo spoke with Us Weekly to confirm that “they have talked about their future and marriage… They don’t have a set deadline in place, but they’re very much in love.” But before Swift walks down the aisle, it’s worth taking a look back on one of her past relationships that everyone but diehard “Swifties” may have forgotten about. In 2012, Swift dated the grandson of Robert F. “Bobby” Kennedy, Conor Kennedy, and in just a short time, the pair raised eyebrows over their age difference and even drew the family’s ire by crashing a wedding.

Here is the truth about Taylor Swift’s relationship with Conor Kennedy.

Taylor Swift is a longtime Kennedy fan

InStyle reported that Taylor Swift has been a fan of the Kennedy clan for years. According to a 2019 biography about the dynasty called The Kennedy Heirs, Rory Kennedy first reached out to Swift after learning of her admiration for the family matriarch, Ethel Kennedy. Per InStyle, this led to free concert tickets, film festival outings, and eventually, an invitation from Rory for Swift to spend Fourth of July weekend at the Kennedy compound.

It was there that Swift first met Conor Kennedy, according to InStyle. Because Kennedy’s mother had tragically committed suicide just a few months prior, his father initially saw Swift’s involvement in his son’s life as “a good distraction” (via The Kennedy Heirs), but not everyone was a fan of their burgeoning relationship. 

Swift was criticized for the pair’s age difference (in 2016, she was 23, while Kennedy was just 18 years old and still in high school). Kennedy’s uncle was also suspicious of the scrutiny that he felt Swift’s fame would bring upon his nephew and speculated that Swift “was probably already composing the song about their breakup [even while together],” per The Kennedy Heirs.

Taylor Swift and Conor Kennedy crashed a family wedding

Taylor Swift and Conor Kennedy’s wedding crashing is perhaps the low (or high, depending on how you look at it) of the couple’s short-lived romance. According to InStyle, Kennedy texted his aunt Vicky Gifford Kennedy just an hour before her daughter’s wedding to ask whether he could attend and bring Swift.

Despite being told that the singer’s presence at the event would distract from the bride’s big day, Kennedy and Swift showed up anyway. When Swift was asked to leave, the mother of the bride said the star “seemed to look right past me,” per The Kennedy Heirs. The biography claims that the couple argued later that night, as Swift hadn’t realized she wasn’t welcome at the event.

Swift’s reps denied the whole debacle, explaining that “there’s no truth to Vicky’s claims… Taylor was invited to the wedding and the bride thanked her profusely for being there.” Even so, the damage was done. The now-infamous wedding crashing spelled the beginning of the end, as Kennedy went on to end things with Swift shortly afterwards.

Conor Kennedy broke things off with Taylor Swift after just a few months

According to Radar Online, Conor Kennedy split with Taylor Swift after she “came on way too serious, way too fast.” Speaking to the outlet, an insider close to Kennedy revealed, “Conor’s just an 18-year-old kid and wasn’t ready for anything super serious, but Taylor is looking for her soulmate and it kind of freaked him out with how strong she came on.” The source claimed that Swift “was more obsessed with the idea of dating a Kennedy, then the actual Kennedy she was dating.”

InStyle corroborated the surprising speed of the relationship by reporting that Swift had shelled out a cool $5 million to purchase a house in Cape Cod and be closer to Kennedy. According to The Kennedy Heirs, Kennedy ended things with Swift in September 2016, around two months into their summer fling. A friend of the family allegedly told the book’s biographer that “Conor liked Taylor, don’t get me wrong, but this business of her buying a house on the Cape made him nervous. It seemed as if she was getting a little too attached, spending five million bucks on a house just to be near the guy.”

After the breakup, Swift sold the Cape Cod house and pocketed $1 million in profit, per InStyle.

Taylor Swift immortalized Conor Kennedy in song

It’s no secret that Taylor Swift has turned her relationships into multimillion-dollar albums by writing telling lyrics about her exes. Though she plays coy on sharing the dirty details, she scatters hints in liner notes, leaving the interpretation up to her fans. Swift and Conor Kennedy may have only dated for two months, but this didn’t exempt him from being included in several of Swift’s hit songs, including “Begin Again,” “Starlight,” and “Everything Has Changed,” according to Cheat Sheet.

“Begin Again” is Swift’s second single from her Red album, and describes “when you go on that first date after a horrible breakup,” Swift told Good Morning America, as reported by The Boot. While any number of Swift’s famous exes could have inspired the “horrible breakup,” the timing points to the song being about meeting Kennedy.

“Starlight” never made it onto the Billboard Hot 100, but it tells the sweet story of Kennedy’s grandmother, Ethel, meeting her husband (per Cheat Sheet). The liner message is telling and reads simply, “For Ethel.” “Everything Has Changed” is a song “about realizing your life has flipped upside down after falling for someone new,” Swift told Digital Spy, (via Genius). Here, the liner note spells out “Hyannis Port,” which is the location of the Kennedy’s waterfront compound (per Cheat Sheet). 

Taylor Swift and Conor Kennedy might not have lasted long, but at least we’ll always have these ballads to remember them by.

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