Red Flags In Taylor Swift's Past Relationships Before She Found Her Happy Ever After With Travis

Just like that, Taylor Swift is officially in her fiancé era. Swift and her partner Travis Kelce announced their engagement on Instagram with a swoony series of photos that looks like the fairy tale fantasy Swift has been dreaming off since before she first penned the lyrics of "Love Story."

In Kelce, Swift appears to have found a partner who adores her and celebrates her passions and work. Mutual support and enthusiasm is part of the science behind Swift's winning relationship with Kelce, since both partners have showed up proudly for the other. Kelce made it to several stops of the Eras tour and Swift has been serving ultimate WAG glam at Chief's game days. "They were corny together so I knew they'd last 🥂," wrote one Reddit commenter. "Congrats to them." Another wrote: "Went from 'and I wouldn't marry me either, a pathological people pleaser' to this and I am ecstatic." Because while Swift might have found her golden love now, she's had to navigate plenty of rocky relationships in the past.

Taylor Swift made a featured appearance on John Mayer's 2009 song "Half of My Heart," and was later romantically linked to the songwriter. Then, Mayer was a heavy hitter in the industry — a longtime staple of popular radio — while Swift was still a relative newcomer. That unequal power dynamic was made even more extreme by their significant age gap: Mayer was 32 at the time, Swift was just 19.

By then, Mayer had already developed something of a bad boy reputation after fraught public romances with stars like Jennifer Aniston and Jessica Simpson. In a 2010 interview with Playboy, Mayer made degrading comments about then-ex Simpson, describing her as "sexual napalm," and bragged about his pornography addiction.

Significant power imbalances and a pattern of disrespect and objectification of women are both major relationship red flags. So, predictably, Mayer's tryst with Swift also ended in heartbreak. Mayer is among Swift's exes who have spoken out about their relationship, and he had mostly nice things to say when asked about her after their split. But Swift was harsher, detailing the ups and downs of her love affair with Mayer on her third album, "Speak Now," including the harshly critical track "Dear John." With the line "Don't you think I was too young to be messed with?," Swift made it clear that the age and experience difference created a problematic relationship that left her disempowered and hypervigilant.

In 2012, Taylor Swift was linked to Conor Kennedy, son of Robert F. Kennedy, for a summer romance that raised some serious red flags. The 22-year-old singer was four years older than Conor Kennedy, which is not an insignificant age gap for people in their late teens and early 20s, and he was arguably in a particularly vulnerable place as his mother had recently passed.

But, more concerning, the love affair escalated quickly, fueled by Swift's public fixation on her boyfriend's famous family. Despite the relationship only lasting a few months, Swift reportedly went with Conor Kennedy to visit his mother's grave,  crashed a Kennedy wedding and refused to leave, and purchased a house near the famous Kennedy compound in Hyannis Port, Massachusetts. She also developed a friendship with Kennedy matriarch Ethel Kennedy, and wrote the song "Starlight," which illustrated Ethel and Robert Kennedy's iconic love story. That's a lot for a new relationship. "It is easily the creepiest thing she has done," observed one Reddit commenter. "The way she tried to Single White Female into becoming a Kennedy – dressing the part, crashing a wedding, dating a high schooler, buying a house nearby right after his mom committed suicide, visiting the grave."

Swift's intensity and preoccupations with the Kennedy dynasty suggest this was a relationship founded more in limerence than real love, which inevitably makes for unstable dynamics. Limerence prioritizes a romantic fantasy over genuine, healthy intimacy. Swift is far better off with a partner whom she respects and understands as an individual.

Taylor Swift's relationship with Jake Gyllenhaal was another significant age gap relationship for the young singer, who was just 20 when she dated the then-29-year-old actor. The age difference is concerning, as was Gyllenhaal's alleged disrespect for Swift's career as a pop singer, which she hinted at with the line "You would hide away and find your peace of mind, with some indie record that's much cooler than mine" on the track, "We Are Never Ever Getting Back Together." Fans widely interpret the lyric to mean that Gyllenhaal looked down on Swift's work; such contempt is a major sign of an impending split, according to relationship expert John Gottman.

But in addition to these dynamics, there was another major red flag in Swift's relationship with Gyllenhaal. Based on Swift's lyrics, fans believe the pair split up and reconciled on multiple occasions.While reconciling with a former partner isn't inherently problematic, it's important to know when to cut your losses and stop going back. "There is a lot of love in this kind of cycle but also a toxic lack of skillfulness," said clinical psychologist Gemille Cribbin in an interview with GQ. "You need to realise that the good times and the parts you love about your partner have never been enough to sustain your relationship, and you need to wake up and commit to putting in the hard work needed to change how you deal with the bad times and parts."

Following her six-year relationship with Joe Alwyn, Taylor Swift allegedly entered into a messy summer romance with The 1975 frontman, Matty Healy. Although neither party publicly announced their romance, this was soon deemed another Swift affair that seemed to escalate quickly, with the singer mouthing the words "I love you" from "The Eras Tour" when Healy was in the audience But the torrid love story crashed down almost as quickly as it had begun, concluding with a sprawling album of angry and heartbroken songs, including "The Smallest Man Who Ever Lived," which Swift fans believe is about Healy.

Moving too fast is a big red flag in a relationship, and it's one that Swift is not a stranger to. But her fling with Healy had other warning signs, including her recently ended relationship with Alwyn. It's clear that Swift jumped straight from her committed relationship to her tryst with Healy, and some fans have even speculated that she may have cheated. "If she didn't cheat physically, she certainly did emotionally," wrote one Reddit commenter. Unfortunately, infidelity in one relationship is a major predictor of infidelity in future relationships, according to a study published in the Archives of Sexual Behavior. Additionally, because Swift did not give herself adequate healing time, this pairing was giving rebound, a glaring sign it was never built to last.