Lily Allen’s dating history: From Harry Potter’s Rupert Grint to Stranger Things’ David Harbour
From chart-topping hits to headline-grabbing romances, Lily Allen’s love life has often shared the spotlight with her music.
Lily Allen’s dating history: From Harry Potter’s Rupert Grint to Stranger Things’ David Harbour
From chart-topping hits to headline-grabbing romances, Lily Allen’s love life has often shared the spotlight with her music. Her 2024 divorce from David Harbour has been thrust into the public eye, fueled by the late 2025 release of West End Girl, an album that hints at infidelity and gaslighting. But it's pot calling the kettle black for Lily who had her own affairs...
Rupert Grint (2008)
Following her split from Ed Simons in 2008, Lily Allen found herself spending time with a very familiar red-haired Brit. She struck up a friendship with Harry Potter star Rupert Grint after meeting at the Order of the Phoenix premiere, and the pair were soon spotted hopping between London restaurants.
An insider told the Daily Star: “After Lily’s split from Ed [Simons], Rupert offered a shoulder to cry on. Last week they enjoyed a Japanese meal together. They had a really long and intense talk, but also lots of fun, too. They get on really well and he makes her laugh… Rupert drove Lily to the restaurant in his black mini and sheltered her from prying eyes.”
Jay Jopling (2009)
In 2009, Lily Allen, then 23, raised eyebrows after being spotted kissing and cuddling with millionaire art dealer Jay Jopling, who was 45 at the time, while holidaying on a yacht in St Barts. The sun-soaked romance may have been short and sweet, but that didn’t stop the rest of the world having a complete meltdown over it.
Sam Cooper (2009-2018)
Lily Allen’s most significant relationship began in 2009, when she met builder and decorator Sam Cooper. Their relationship moved fast with Sam proposing on Christmas Day 2010 during a trip to Indonesia in Bali. The couple tied the knot six months later at St James the Great church in Cranham, Gloucestershire. They went on to have two daughters, Ethel Mary, born in November 2011, and Marnie Rose, who arrived in January 2013. However, their happily ever after was anything but. It was a tumultuous relationship marked by devastating loss. Allen had been expecting a baby boy, George, due in early 2011, who was tragically stillborn.
Opening up to The Sun in 2010, she said: “It’s something that I still haven’t dealt with. I never will get over it. I have dealt with it, you know, as being at one with it. But it’s not something that you get over. I held my child and it was really horrific and painful – one of the hardest things that can happen to a person.”
Cracks in their relationship began to show, with Allen later confessing to multiple affairs, including hiring female prostitutes, and revealed in her memoir My Thoughts Exactly that she had a relationship with Oasis frontman Liam Gallagher while both were married.The pair separated in 2016 and officially divorced in 2018. Today, they share custody of their daughters.
Liam Gallagher (2015)
Also in her memoir, the Not Fair hitmaker revealed she had an affair with Wonderwall singer Liam Gallagher, who was married to Natalie Appleton at the time. With Allen admitting their encounter was anything but random.
She wrote: “There was a particular celebrity that I was really after, romantically, and I looked at his touring schedule and he was gonna be in Japan. So I made sure that I was at this festival and that I would be one of the very few English-speaking people at the same festival as him.”
Allen and Gallagher became official members of the mile high club on a flight to Japan’s Fuji Rock Festival in 2009.
David Harbour (2019 - 2025)
Lily Allen’s whirlwind romance with Stranger Things star David Harbour began in 2019 and moved at full speed. Just a year later, the couple tied the knot in a very on-brand Las Vegas elopement in 2020, complete with an Elvis impersonator officiating the ceremony.
By 2025, however, the marriage had come to an end. Insiders told People: “Her marriage has been crumbling and they have split….[It’s been] very hard for her and her girls.”
Allen later unpacked the breakdown of their relationship on her 2025 album, West End Girl. Across several tracks, she hinted that Harbour crossed boundaries within their “open” marriage. On “Madeline,” she spelled out the key rule: “It had to be with strangers.”
