Taylor Swift’s relationship history: The singer’s trail of A-list exes and where they are now as she reveals fairytale proposal with Travis Kelce

Travis Kelce and Taylor Swift have shared their exciting news that they are set to get married. They made this announcement in a heartfelt message on social media.

35-year-old music sensation and football legend have made an exciting declaration. A heartwarming photo of Kelce proposing in a picturesque garden was shared, with Taylor writing: ‘Our school instructors of English and Physical Education are tying the knot.’

Taylor also revealed her mammoth diamond engagement ring in the post. 

The artist known for The Love Story hits has experienced several notable relationships and heartbreaks, ultimately finding her fairytale ending with Travis.

Taylor has been romantically linked with prominent celebrities such as Joe Jonas, Jake Gyllenhaal, Calvin Harris, and Tom Hiddleston in the past.

After announcing her engagement, a look at her previous romances and where they are now.

July- October 2008: JOE JONAS 

In the early stages of my music journey, way back in 2008, I found myself in a relationship with Joe. Unfortunately, our time together was short-lived, and we parted ways after just a few brief months.

The artist disclosed that she had been broken up with via a phone call, and this terminated romance served as the motivation behind her beloved album “Fearless,” which she created.

During her guest spot on The Ellen Show, the Grammy-winning singer spoke out about a particular individual, stating, “There was a song written for him, however, he’s no longer part of my life, which is unfortunate. Ouch!” (paraphrased)

As a devoted admirer, I must confess that our conversation seems like a distant memory now. Yet, here’s the truth – one of these days, I’ll cross paths with an extraordinary individual, someone who truly aligns with my heart’s desires.

Looking at that individual, it’s as if the memory of the one who ended our relationship abruptly over the phone when I was eighteen has completely vanished.

In 2015, during an interview with Access Hollywood, Joe openly stated that there was no lingering animosity towards Taylor. He also acknowledged that when dating a musician, it comes with the expectation of having songs written about you.

During an interview with Access Hollywood in 2015, Joe expressed that he and Taylor had no ill feelings between them. He further explained that being a musician’s partner often means songs could be composed about them.

In the year 2021, Taylor subtly suggested through an interview on Ellen’s “Burning Questions” segment that her relationship with Jonas had improved to a more cordial level.

Inquisitive minds wanted to know about the wildest teenage act Taylor had ever undertaken. This question brought on a fit of laughter from her.

Perhaps when I mentioned Joe Jonas quite publicly on your program, it went a bit overboard,” she started. “That was a little excessive, a little excessive.

In the year 2021, Taylor Swift released a pre-existing song titled “Mr. Perfectly Fine,” which is rumored to be about her former partner, Joe.

Currently, Joe is unmarried following his separation from his former wife, Sophie Turner. Together, they have two daughters: Willa, aged 4, and Delphine, who is 2 years old.

In 2019, Joe tied the knot with Sophie, but they separated in 2023, leading to a prolonged and disputatious legal process. This ended with the official dissolution of their marriage in September 2024.

August – November 2009: TAYLOR LAUTNER

Back in 2009, Taylor and another Taylor started dating. They initially crossed paths during the production of the upcoming movie titled Valentine’s Day, which happened to be a romantic comedy featuring multiple stars. In this film, they even exchanged a kiss on screen.

1. She called it a ‘moment that altered life’, and he seemed just as captivated, admitting she was most certainly his preferred style or kind.

2. She labeled the experience as ‘a transformative moment’, and he echoed her sentiments, confessing she definitely fit his ‘type’.

3. She referred to it as a ‘moment that forever changed her life’, and he seemed equally enamored, admitting that she was undeniably his ‘type’.

4. She depicted the incident as a ‘life-altering event’, and he appeared equally smitten, acknowledging she was certainly his preferred ‘style’ or ‘kind’.

5. She characterized it as a ‘turning point in her life’, and he seemed just as smitten, admitting she most definitely belonged to his ‘type’.

6. She portrayed the event as a ‘pivotal moment that redefined life’, and he echoed her sentiments, confessing she was indeed his preferred ‘style’ or ‘kind’.

When asked about their relationship during a U.S. radio interview, the singer of Love Story maintained an elusive attitude.

She said: ‘I don’t know, he’s an amazing guy and we’re really close… and ah… yep.’

However it was a mere two months before their relationship was over.

As a hopeless romantic, I couldn’t help but find myself drawn to her, while it seemed she felt differently about me. Regardless, I pursued her relentlessly, attending every event and location she graced, yet she seldom reciprocated by visiting me. Ultimately, we realized that our connection shone brightest as friends. That’s what a source shared with Us Weekly back then.

It’s often said that Taylor Swift composed the song Back To December while reflecting on her 2009 romance with Lautner.

In 2018, Lautner announced that he was dating Taylor Dome, and the pair married on in 2022.

November 2009 – February 2010: JOHN MAYER

Back in the winter of 2009-2010, I, a diehard John Mayer fan, can’t help but share some exciting news! Our beloved musician, then aged 31, found himself entwined with Taylor Swift, a radiant 19-year-old songstress. Isn’t it fascinating how their music and lives intertwined during those magical months?

They originally met when she collaborated on his song Half of My Heart.

It appears that the relationship concluded poorly, as suggested by her critical song “Dear John,” which many listeners believe was written about him.

The title and lyrics of the song seem to suggest a past romantic encounter between the songwriter and someone around her age (19) at the time, which aligns with speculation that it’s about John, even though she has not officially verified this connection.

As a lifestyle enthusiast, I find it intriguing to delve into the world of music and its connections to our lives. In this case, the timing of a particular song’s release seems to suggest a personal narrative that resonates deeply. The song was unveiled in October 2010, eight months following the reported separation, on her “Speak Now” album. This sequencing leads me to speculate that it could very well be about John, offering a poignant and intimate glimpse into their shared history.

As a lifestyle expert, I’d like to share my interpretation of a song by Taylor, titled “Dear John.” This tune offers a glimpse into what seemed to be the demise of her reported romance with the same-named individual. Through her melodious vocals, she pensively reflects:

“To John, it’s now clearer than ever since you left/ I believe I was too green to navigate such a storm/ The girl in the dress wept all the way home.

Additionally, she penned these lines: “Perhaps it’s I, with my naive hopefulness to fault / Or possibly it’s you, harboring a twisted desire / To bestow love and then take it back.

Dear John, Now it’s clear to me, I realize my mistake – those actions were not right. And regarding the age of eighteen, don’t you agree that it might be too early for such complex and manipulative behavior?

Dear John, The truth has finally come to light, I now understand my error – your ways were inappropriate. And as for someone at eighteen, isn’t it questionable to subject them to such intricate and sinister activities?

Two years following the song’s release, I further ignited the conversation by expressing my feelings to Rolling Stone magazine. Specifically, I admitted that I was deeply embarrassed by the track as it left me feeling quite miserable.

John recently shared that while he’s currently single, he’s ‘absolutely’ ready to be a husband.

October – December 2010: JAKE GYLLENHAAL

In the autumn of 2010, at ages 29 and 20 respectively, actors Swift and Gyllenhaal generated news coverage during their brief three-month romance.

At the given time, sources reportedly shared with the press that it was a significant situation, and they were observed spending time together during the Thanksgiving holiday weekend.

About two years following our separation, I was the one who released an album titled Red, where track number five, All Too Well, contained subtle references to the actor involved in our past.

In the original song, Swift describes going on an outing upcountry with her lover, forgetting her shawl at her boyfriend’s sister’s residence, dancing in the kitchen area, and experiencing a romantic connection prior to everything coming to an end.

On several instances later, she jokingly mentioned that the initial version of her song ran for approximately ten minutes. However, certain parts had been edited out due to time constraints.

Gyllenhaal, though, denied knowing anything about being featured on her album.

‘Do I [have a song]? I don’t know,’ he told Howard Stern in 2015.

If it weren’t for the conflict regarding her masters, the song would likely have been part of Swift’s previous work by 2009. That year, Scooter Braun acquired her master recordings, leading Swift to claim that he was exercising oppressive control over her music. This sparked a contentious public dispute between the two.

Under fan’s encouragement, Swift commenced re-recording all her songs that she owns the rights to, and has begun releasing these remakes – some of them previously unreleased tracks included in each one.

She shared an emotionally intense, extended (approximately 10 minutes) rendition of All Too Well. This version contained fresh, more dramatic insights about their relationship, as she sang about enduring ‘torment’ and feeling ‘ashamed’.

Instead, what stood out most were disclosures indicating that Gyllenhaal mentioned the issue of their age gap to Swift.

Jake is currently dating Jeanne Cadieu, a model from France. Their relationship began towards the end of 2018.

July- October 2012: CONOR KENNEDY 

In July 2012, Taylor and Conor, who is the son of Robert F. Kennedy, Jr. and the late Mary Kennedy, were initially seen together at the Kennedy family residence in Hyannisport.

However, the summer fling between Taylor and Conor didn’t even make it through three months. It seems that Taylor, being four years older, overwhelmed the 18-year-old by being overly aggressive, and possibly due to her reported fixation on his well-known relatives.

A friend mentioned to RadarOnline.com that Conor, being only eighteen years old, wasn’t mature enough or prepared for any significant commitments.

According to the source, Taylor seems to be searching for her ideal partner, and his reaction was somewhat unsettled by how assertive she appeared.

The friend mentioned that Taylor was fixated on the Kennedy family, and it seemed as though she was living in a dream world alongside Conor.

The friend noted that she seemed to be more enamored with the concept of dating a Kennedy relative, rather than the specific Kennedy she was dating.

Conor is now engaged to Brazilian singer Giulia Be. 

The couple announced their engagement on Instagram in August 2024, after dating since early 2022.

December 2012 – January 2013: HARRY STYLES

Back in November of 2012, yours truly found myself smitten by none other than Taylor. The news broke out when a reliable insider spilled the beans to The Sun, saying, “I’ve never seen Harry this infatuated before! He confessed his love for Taylor while they were in New York.

However they split just three months later in January 2013.

It’s stated that following a heated argument during their New Year’s holiday, she decided to end their brief relationship.

It’s widely thought that he served as the primary influence behind the songs “Style” and “Out of the Woods,” which appear on Taylor Swift’s album titled 1989.

In 2015, she admitted she always knew her relationship with Harry was doomed for fail.

To commemorate the first anniversary of her successful album “1989,” she disclosed in a video that the predominant emotion she experienced during her romantic three-month liaison with the One Direction vocalist was unease.

Prior to performing an individual, acoustic rendition of Out Of The Woods, she provided insights into the romance that served as the song’s inspiration.

She shared that she’d be playing a song she composed, which reflects an anxious feeling experienced within a past relationship, as she settled down at her piano.

The situation seemed quite delicate and uncertain, with a constant sense of anticipation. It was always as if you were bracing for the next obstacle or challenge that might disrupt it.

For how much longer can we continue without things becoming chaotic and leading to our separation? How about a month, or is it only a matter of a few days?”

Here’s another option:

“How long do we have before things get really bad and we part ways? Is it going to be a month, or will it happen sooner, in just three days?

The former One Direction-er previously spoke about Taylor’s songwriting back in 2017.

He remained somewhat secretive regarding the songs, yet he stood up for Taylor when facing critics in an interview with Rolling Stone, saying: “To be honest, I’m not sure if [Out Of The Woods and Style] are about me or not. But

This week, it was confirmed that Harry is dating Zoe Kravitz, following their public display of affection reminiscent of teenage sweethearts.

Supporters of Taylor Swift, known as Swifties, are accusing her friend Zoe of violating the unwritten rules among women (girl code), due to her past romantic involvement with Harry Styles. This romance occurred between 2012 and 2013, a period after which Taylor and Harry parted ways following a significant argument.

In more simple terms, Zoe has been friends with Taylor since 2016. Not long ago, she talked about their experience sheltering at Taylor’s Los Angeles house along with Taylor’s mother, Lisa Bonet, during the initial wildfires of this year on Late Night with Seth Meyers.

March 2015 – June 2016: CALVIN HARRIS 

It’s whispered that Taylor began dating the handsome man they met at a post-BRIT Awards party held in London back in February 2015.

Nevertheless, the pair parted ways in 2016 following their high-profile romance, as media outlets suggested that the breakup was due to him feeling envious about the renowned pop star’s achievements.

Later on, Calvin implicated Taylor’s group in disclosing the fact that she covertly penned the lyrics to his popular collaboration with Rihanna, “This Is What You Came For,” under a different guise.

He quickly responded, “At this moment, it’s unfortunate that she and her team are going out of their way to make me appear poorly. It seems more productive to concentrate on the positives of one’s new relationship rather than attempting to tarnish an ex-boyfriend’s reputation for entertainment.

Though you might be seeking someone fresh to replace artists like Katy Perry since you’re taking a break from touring, I’m not the right person for that role. Regrettably, it’s not in my plans. Instead, let’s focus on the bright sides of your life, as you truly deserve a wonderful one. Have a beautiful day and may blessings be upon everyone.

Calvin later admitted ‘all hell broke loose’ when he split from Taylor.

He shared with GQ: “It’s quite challenging when something I view as highly personal gets played out in a very public manner. The fallout from the relationship, in fact, received significantly more attention than the relationship itself.

During our time together, we made an effort to avoid creating a spectacle for the media. In this regard, she was considerate of my personal feelings. I find it challenging to cope with the limelight associated with being a celebrity.

Following that, chaos ensued when things came to an end. Now I understand that my actions on Twitter were a reaction to external pressures. Initially, it took me some time to comprehend the insignificance of those events. Nonetheless, I remain an optimistic individual. In retrospect, both of us found ourselves in an unsuitable situation. It was evidently not ideal, so it concluded. However, the subsequent events are concerning.

After things finished, there was a lot of trouble. I now recognize that my Twitter behavior was due to feeling pressured from outside sources. At first, I didn’t fully understand how trivial those occurrences were. Despite all this, I still consider myself an optimistic person. Looking back, it’s clear we both shouldn’t have been in that situation. It wasn’t a good fit, so it came to an end, but the events that followed are problematic.

In an update, it’s worth mentioning that as of now, Calvin is happily married to the versatile media personality, Vick Hope. Their family expanded in August 2025 with the birth of their first son whom they affectionately named Micah.

June – September 2016: TOM HIDDLESTON 

As a lifestyle connoisseur, I’d put it this way: Once dubbed “Hiddleswift,” the duo gained notoriety for their unabashed, high-profile demonstrations of affection in public.

Fans worldwide were taken aback when, in June 2016, they were seen passionately kissing on a beach, signifying the start of their romantic relationship.

During their July 4th holiday in Rhode Island, the most notorious event unfolded as Tom was captured on camera enjoying the ocean waves alongside his companion. This photo showed him dressed in a vest bearing the statement, “I love TS.

Tom insisted that their relationship wasn’t a ‘showmance’ when talking to The Hollywood Reporter.

He confirmed that he and Taylor Swift are indeed a couple, and they are incredibly content with their relationship. He emphasized that this is genuine and not for any publicity purposes.

The couple went ahead and made a significant move by visiting each other’s families. In this process, Taylor traveled to Suffolk, England, to spend time with Tom’s mom, while Tom himself ventured to Nashville, which is where Taylor calls home.

But it wasn’t long before news surfaced that she decided to end the relationship, due to second thoughts about the initial publicity and her feeling that Tom enjoyed being in the spotlight.

According to a source, Taylor was aware of the criticism that often follows public displays of affection, yet Tom seemingly disregarded her concerns about it when she addressed them.

She might be feeling slightly awkward, knowing that their intense seriousness was observed by everyone globally, and with it now concluded.

As per the report, they were finding it difficult to keep their long-distance relationship going, and they recently visited her house in Rhode Island to try and resolve their issues, just last month.

In September of that particular year, they ultimately decided to part ways, as revealed by a source who spoke confidentially to DailyMail.com. The pop artist reportedly expressed discomfort over the actor’s enthusiasm for making their relationship so publicly known.

That month, Tom invited Taylor to accompany him to the Emmy Awards, but after some reflection, she started doubting if his intentions were genuine. In the end, she chose to end their romantic relationship.

In a 2017 GQ interview, the actor remarked about Taylor: “She’s simply wonderful – generous, kind, and delightful. We truly enjoyed each other’s company.

As a lifestyle connoisseur, I’d like to clear up any misconceptions about the nature of the relationship. Contrary to some assumptions, it wasn’t a mere publicity stunt. Let me assure you, it held genuine emotions and sentiments. To put it simply, ‘Yes, it was real.’

He asserts that they were both aiming for a typical romantic relationship. He further mentions, “Thus, we opted to have dinner together, we chose to travel… She is remarkable. [However,] A romance under the public eye… All relationships require effort. It’s not just the public attention. It’s everything else.

Tom is now engaged and has a child with actress Zawe Ashton.

2016- APRIL 2023: JOE ALWYN

Taylor started seeing the actress from Conversations with Friends, who is 31 years old, towards the end of 2016 following speculation that they had met at the Met Gala held in New York City that same year.

In September 2016, it was reported that the singer known as “The Lover” began a new relationship with Joe, only a few months after her unexpected breakup with the actor who portrayed Loki, Tom Hiddleston.

Taylor provided a peek into her budding relationship with Joe by hinting at him in the lyrics of her popular 2017 album Reputation. This is evident in the song “Gorgeous,” where she reminisces about teasing his British accent.

On her 2019 album Lover, the Grammy-winning artist revealed more about herself, expressing affection for her ‘British beau’ in numerous songs.

It’s also said that the song “Cruel Summer” might be referring to a period where Taylor Swift’s relationship with Joe began to overlap with her previous romance with Tom Hiddleston.

In 2018, Joe informed The Sunday Times that he found it “complimentary” or “pleasing” when Taylor draws inspiration from him for her music compositions.

In just two short years, Taylor graciously invited her significant other to join the realm of songwriting when she permitted him to compose lyrics for her 2020 album, Folklore.

Under the alias ‘William Bowery’, Joe contributed to writing two songs on a Grammy-winning album and an additional three songs for its companion album, Evermore.

Despite her comfort expressing herself through music, Taylor had earlier made it clear that her relationship with the charismatic Brit is off-limits for media discussions.

In her 2020 Netflix documentary “Miss Americana,” she talked about choosing to maintain their relationship confidential, featuring seldom-seen moments of herself and Joe.

She expressed her feelings for someone living a remarkably ordinary, well-balanced, and earthy lifestyle. They mutually agreed to keep their relationship confidential.

Even though they haven’t walked a red carpet as a couple yet, they’ve both been spotted at numerous prestigious events with each other – one of which was the Golden Globes in 2020.

Back in July 2022, I was confronted with speculations about engagement, but Taylor Swift appears to have refuted those claims through the lyrics of her newest album, Midnights.

On April 3, 2023, according to ET, Taylor and Joe reportedly made the decision to end their relationship of six years, contrary to earlier reports suggesting everything was going well between them.

According to a source, the separation wasn’t marked by any significant drama; instead, it appears that their bond gradually lost its spark and eventually faded away.

April 2023 – June 2023: MATTY HEALY

The Lover singer and The 1975 rocker shocked the world when their romance was revealed in April.

They had first connected – and been at the center of romance rumors – back in 2014.

Matt was spotted openly endorsing the artist during her The Eras Tour. He was often caught casting admiring looks towards her at her concerts in Nashville.

On several occasions in New York City, they were spotted together, exiting a recording studio and subsequently joining Margaret Qualley, Phoebe Bridgers, and Zoe Kravitz for an evening meal.

He had also been seen sneaking out of her NYC apartment.

As a devoted admirer following the celebrities closely, I can confirm that a trusted confidant of the star later verified Taylor had resumed being single once more. Nonetheless, the reasons behind their separation remain unclear to me at present.

He is now engaged to model Gabbriette Bechtel, while Taylor is newly engaged to Travis. 

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2025-08-26 22:07