After Healy was spotted wearing 1989 merch onstage in November 2015, Swift went to a 1975 concert, where she reportedly met the singer for the first time. (Later, she was photographed wearing a 1975 T-shirt.)

Later that month, Healy was asked about Swift during an interview with Shazam Top 20. “I met Taylor Swift, that was really nice,” he said at the time, per E! “We exchanged numbers. Let’s see what happens.”

When asked if he planned to call her, Healy reiterated, “Let’s just see what happens.” He continued, “I mean bloody hell, what am I going to do? Go out with Taylor Swift? She’s a sensation, I wouldn’t say no.”

A couple months later, Healy shut down the rumors that the duo had been secretly dating. “It’s fake. It’s all bloody fake. It’s a farce!” he told Australia’s 2DayFM, per E!.

“We met each other, we exchanged numbers in the same way that a lot of people in this kind of world do, and we spoke occasionally,” Healy explained at the time. “She’s the biggest pop star in the world and I’m in Australia. There’s no relationship or anything happening. It’s just funny how people really, really buy into that.”

“It really didn’t happen,” Healy said before adding, “It would be amazing for me if it did.”

By March 2016, Healy had changed his tune on the possibility of dating the “Blank Space” singer. In an interview with Q, he opened up about the relationship rumors surrounding him and Swift.

“The one time I did have a flirtation with a girl it ends up going everywhere … people were like, ‘Who’s Matt Healy?’ so that was cool,” he said. “But I didn’t make a big deal out of it myself. It’s not really anything to talk about, because if she wasn’t Taylor Swift we wouldn’t be talking about her.”

Healy added that he was “absolutely” concerned by the possibility of losing himself in a relationship. “If I had gone out with Taylor Swift I would’ve been, ‘F*cking hell! I am NOT being Taylor Swift’s boyfriend,’” he said.

“You know, f*ck that,” Healy added at the time. “That’s also a man thing, a de-masculinating, emasculating thing.”

Swifties almost got a collab from Swift and The 1975 on Midnights. In November 2022, Healy revealed that they worked together, but it was never released.

“We actually worked a bit on that but then the version of it never came out," he said on KROQ’s Klein/Ally Show for Audacy’s DTS Sound Space, per People. But there were no hard feelings over the decision. “It was for reasons that are not to be criticized ... She’s amazing,” Healy clarified.

In January 2023, Swift performed her song “Anti-Hero” live for the first time at a 1975 concert in London. Fans pointed out that Swift sported folklore hair — specifically, her “Cardigan” music video hair — and a “Mirrorball” dress for the performance.

Now with the context of Tortured Poets, this has prompted a new fan theory that “Cardigan” is actually about Healy. A few months later, Swift seemingly pointed at Healy in the VIP tent while performing the track — which is about two people finding their way back to each other, BTW — and she even mouthed a not-so-secret message mid-song (but more on that later).

That’s not all. Fans think “Peter” on TTPD is about Healy, and there’s a line in “Cardigan” that mirrors that same metaphor: “Peter losing Wendy.”

In April, reports began swirling that Swift and Joe Alwyn had broken up. The next month, Swift and Healy started spending more time together.

They were spotted on a date at Casa Cipriani in NYC on May 11 and were photographed outside of Electric Lady studio a few days later, seemingly confirming dating rumors.

On May 3, The Sun reported that they were together. “She and Matty are madly in love. It’s super-early days, but it feels right. They first dated, very briefly, almost ten years ago but timings just didn’t work out,” a source claimed at the time.

Around this same time, both Swift and Healy mouthed the words, “This is about you, you know who you are. I love you,” while performing onstage. Healy also made an appearance at a few of Swift’s Eras Tour shows — he even performed with opener Phoebe Bridgers at Swift’s Philadelphia show.

Only a month into their ’ship, Swift and Healy reportedly called it quits. On June 5, a source told Entertainment Tonight, “Taylor and Matty broke up. They are both extremely busy and realized they’re not really compatible with each other.”

The insider continued, “Taylor’s friends want what’s best for her and aren’t shocked that their relationship fizzled out since she recently got out of a long-term relationship.”