Liam Payne had a number of famous relationships before his sudden death at 31 years old.

The One Direction singer died on Oct. 16 after falling from a hotel balcony in Buenos Aires, Argentina. He was spending time in the country with his girlfriend, Kate Cassidy, whom he included in his final social media posts just hours before he died.

“Liam, my angel. You are everything,” Cassidy wrote on her Instagram Stories in a touching tribute two days after his death. “I want you to know I loved you unconditionally and completely. I will continue to love you for the rest of my life. I love you Liam.”

Prior to Cassidy, Payne was engaged to his ex, Maya Henry, and welcomed a son, Bear, with his former partner, Cheryl Cole. He also previously dated Danielle Peazer and Sophia Smith. Following his 2021 breakup with Henry, Payne admitted that he felt he struggled being in relationships in general.

“I feel like more than anything at this point, I’m more disappointed in myself that I keep on hurting people. That annoys me,” he said in a June 2021 interview on The Diary of a CEO podcast. “I’ve just not been very good at relationships. And I know what my pattern of things is with relationships, I feel at this point.”

Here’s a look back at Liam Payne’s dating history.

Payne’s first public relationship was with Peazer, whom he started dating in 2010 when he was 17 years old and she was 22. Peazer was a dancer on The X Factor, where she met Payne as he competed on the show.

The two went on to date for three years, before calling it quits in 2013. After Payne’s death, Peazer posted a touching tribute on Instagram, writing that at one point, the late singer was her “favorite person in the whole world,” while recognizing they still had their differences. “You could also wind me up so much and I probably annoyed the hell out of you sometimes too,” she wrote.

She went on to reflect on their relationship, explaining that though it ended over a decade ago, the two remained friends through the years and stayed in contact.

“Our relationship may have ended back in 2013, but that seemed to be just the start of our story,” Peazer wrote. “The things we went through and experienced from then all the way until last year could be described as unique to some and misunderstood by others, but I think deep down we always knew we’d have some sort of connection forever, no matter where our individual lives took us.”

Peazer has since been in a relationship with radio DJ Sonny Jay and the two welcomed a daughter, Mia, together in May 2024. The backup dancer shared that she spoke to Payne as recently as a few weeks before his death, in which he took the time to congratulate her on her growing family.

“Receiving a message from you a couple of weeks ago expressing your happiness for the love I found with Sonny and Mia is something I’ll cherish forever,” she wrote.

Following his breakup with Peazer, Payne began dating his childhood friend Smith in May 2013. The pair had first met when they were both students growing up in Wolverhampton, England.

“I didn’t actually go out with her at the time [when we were younger],” Payne said in a September 2015 interview with Attitude. “I used to see her at school and we’d kind of chat. I asked her sister for her number. She was very shy and didn’t give much indication that she liked me, so I just assumed that she wasn’t interested, as well as thinking, she was way too hot for me anyway.”

The two even talked about marriage, he said, though ultimately decided against it as both were in their early 20s at the time.

“Sophia needs to go off and do what she wants to do,” he said. “I don’t want her to be one of those stay-at-home girlfriends who doesn’t really do much.”

Due to his busy touring schedule and their busy lives, Payne and Smith ultimately broke up in October 2015, a source confirmed to PEOPLE at the time.

“I’m absolutely devastated to have split with Sophia,” Payne told The Sun. “Being on the tour all this year and being away from her was so hard. We spent so much time apart. But in order to do right by somebody sometimes it’s better not to do what your heart wants, but to do what’s better for them.”

Though Payne and Cole, an English singer part of the girl group Girls Aloud, had first met at Payne’s The X Factor audition when he was 14, it wasn’t until late 2015 that the two started dating.

Cole was a judge on the show when Payne auditioned the first time, and again when he reapplied when he was 16 (Cole was 26 at the time). In a May 2017 interview on The Radio 1 Breakfast Show, Payne said he and Cole “don’t like to talk about” their 10-year age gap and admitted that he “always, always had a crush on” the singer, even famously throwing her a wink at the end of his audition.

“I got back to school the next day and when my friends saw it they were literally ripping the piss out of me. Now they can’t say it didn’t work,” he said, joking, “The wink is powerful, it has powers beyond its own means. I have to be careful — it’s a licensed weapon in the UK.”

In November 2016, PEOPLE confirmed Payne and Cole were expecting their first child together, and their son, Bear Grey, was born on March 22, 2017. However, a year later, in July 2018, Payne announced that he and Cole had split and were focused on coparenting Bear together.

The two maintained a strong coparenting relationship since, and Cole posted a tribute to Payne after his death, asking the public for privacy as she admitted she was it was “breaking [her] heart” that she “cannot protect” Bear from seeing details about his father’s death.

“Before you leave comments or make videos, ask yourself if you would like your own child or family to read them,” she wrote. “Please give Liam the little dignity he has left in the wake of his death to rest in some peace at last.”

A month after breaking up with Cole, Payne was tied to model and influencer Maya Henry, though the two didn’t make their relationship Instagram official until September 2019. At the time they started dating, Henry was 18, and Payne was 24. By August 2020, the two confirmed they were engaged.

However, a year later, the couple briefly split, with Payne confirming their break up on The Diary of a CEO podcast.

“I’m just not very good at [relationships] so I just need to work on myself before I put myself on to somebody else,” he said. “And I feel like that’s where I got to in my last relationship.”

Despite the split, Payne and Henry seemingly got back together by March 2022, with Payne stating that “she’s still my fiancée.” A few months later, in May 2022, they called it quits for good.

In May 2024, Henry released a fiction book, Looking Forward, that she told PEOPLE was heavily inspired by her own story dating Payne. In the novel, the main character, Mallory, experiences domestic abuse and is pressured to have an abortion, something Henry said she related to in her own life.

“I definitely chose to forgive a lot of things,” she told PEOPLE, referring to her relationship with Payne. “When you love someone so much, you have those rose-colored glasses. You’re in denial, so you think those things will stop, and they don’t, and that just becomes an issue among other issues.”

Just a week before Payne’s death, Henry issued a cease-and-desist letter, according to the Daily Mail, explaining in a TikTok posted days before his fall that the singer allegedly repeatedly contacted her from different numbers following their breakup.

Payne was first seen with Cassidy in October 2022 and was dating her at the time of his death in October 2024. In the days after, Cassidy posted a tribute on Instagram, writing that she was “at a complete loss.”

“Nothing about the past few days have felt real,” she continued. “I ask and pray that you’ll give me the grace and space to navigate this in private.”

A source close to Cassidy told PEOPLE soon after that the model had stood by Payne during his “legal drama” with Henry.

“She had been super supportive of him through all the legal drama and very much stood by him,” they said, after another source close to the situation told PEOPLE that Payne was “extremely overwhelmed by all of the legal issues.”