The “Slow Hands” singer was first linked to the luxury shoe buyer in July 2020, with the Daily Mail reporting that they had been together for about two months after getting to know one another during quarantine. Though they haven’t publicly commented on their romance, Horan and Woolley made their red carpet debut at a charity gala in September 2021.
Before hitting it off with his new love, the former One Direction member dated Hailee Steinfeld for less than one year in 2018. “I’m a bad communicator in relationships. I struggle to talk about things. I don’t like to let things build up in me and songwriting does help get it out but it can happen too late,” Horan told Fault Magazine in March 2020, while reflecting on how their split influenced his album, Heartbreak Weather. “With any relationship, there are fun moments and there are days when you feel like you’re in a music video with the rains pouring outside as you watch crying through the window.”
He continued: “When you go through a breakup you process the whole relationship and think back to amazing nights times together and the bad ones and I wanted that for this album. I wanted to show the full narrative and create a different kind of breakup album.”
Steinfeld, for her part, seemingly shared her side of the breakup on her song, “Wrong Direction,” which was released in May 2020. “What’s so strange about music is you write it and then you’re in that headspace obviously when you’re writing it and then it’s done,” the Oscar nominee said during an interview on SiriusXM Hits 1’s The Morning Mashup at the time. “You can pack that away and move on to the next song. Then all of a sudden you’re, like, performing and you’re like, ‘OK, this is still very much attached and it’s just like I never left the studio.’”
The Dickinson star hinted about what caused her and Horan to call it quits the following year. “I want a partner who is, first and foremost, loyal and honest but confident in themselves and able to do their thing while I do mine,” Steinfeld told Cosmopolitan in November 2021. “It’s weird talking about it because it’s been in my head for so long. … I also think there’s power in claiming what you want, and maybe what you want is not to be alone.”
Things ended on a much more positive note with another one of Horan’s exes, “We’re still friends,” Ellie Goulding, who was briefing linked to the Ireland native in 2013, told Seventeen three years later. “We went on a few dates, and it was really fun. He’s a really, really lovely guy. He’s got the biggest sense of humor, he’s very caring, and I see him as a genuine friend in the industry.”
Keep scrolling to see all of the leading ladies that Horan has been linked to over the years: