Lily Allen's marriage - and subsequent split in 2024 - from Stranger Things alum David Harbour was the latest development in her dramatic love life. The Grammy Award-nominated singer-songwriter has generated countless headlines for her two marriages - first to Sam Cooper and then to Harbour - as well as for her frank comments about her romantic prospects for the future. "The dating scene is much harder as a 40-year-old woman with two teenage children than it is for a 34-year-old woman," she admitted to Paper Magazine in October 2025. "It's bitterly disappointing. There's an element of humiliation and shame around it. The world doesn't portray women of my age as being desirable." She went on, "[Dating] just feels like climbing up a mountain. But also, at the same time, I'm like, I don't have to get involved with it. But something in me says that I do." Lily Allen Recalls Spotting Her Own 'Red Flag' Behavior With 1st Boyfriend Keep scrolling for a look back at Allen's dating and marriage history. Ed Simons Lily Allen, Ed Simons. Getty Images (2) Shortly after the release of her debut single, "Smile," Allen started dating Ed Simons, who is half of the electronic music duo Chemical Brothers. Allen's spokesperson announced the singer was expecting her first child with Simons three months later. "As the pregnancy is at a very, very early stage, the couple ask that you respect their privacy," her representative told People in December 2007. "The couple will be making no further comment but they are obviously both thrilled by the news." It was reported in January 2008 that Allen suffered a miscarriage and her relationship with Simons ended soon after. Liam Gallagher Lily Allen, Liam Gallagher. Getty Images (2) Rumors swirled in the British press for nearly a decade that Allen hooked up with Oasis frontman Liam Gallagher on an airplane while he was still married to his ex-wife Nicole Appleton. (Gallagher and Appleton were married from 2008 to 2014, and they share a son, Gene Gallagher.) Appleton seemingly lent credence to the accusations by tweeting in April 2018: "One day our paths will cross @lilyallen!" Allen initially attempted to downplay the airplane hookup rumors when asked about them by The Guardian in May 2018. "I mean, I haven't said one thing [to suggest that]. I literally have never said anything." she insisted. "Nine years ago, they first tried to print this story, and I didn't say anything then. And now Nicole Appleton, bless her, she's reacted to it, so that's made it seem real. Now my Twitter feed is: 'Oh, stupid attention seeker, she just wants another minute in the limelight.' But I literally haven't said anything. I haven't even liked a tweet. Nothing." However, Allen eventually claimed in her memoir My Thoughts Exactly that she did hook up with Gallagher while they were traveling to the FujiRocks festival in 2009. "We got hammered on the plane," she recalled. "At some point Liam and I found ourselves together in the toilet doing something that he shouldn't have been doing, and it wasn't drugs. Then we were in a lie-down bed together. When we landed in Tokyo, Liam said, in his distinctive nasal twang, 'What you doing now? Why don't you come back to our hotel' ... I was like, 'Yeah, OK.'" Allen insisted that she was not aware that Gallagher was married until after they'd already hooked up in Tokyo. "It wasn't until the next day when he said something like, 'No one can hear about this because of Nic,' that I clocked he was married," she wrote. "I knew [Liam's brother] Noel [Gallagher] was married and I knew Liam had been married to Patsy Kensit. That was partly why I fancied him. I'd grown up an Oasis fan. I was 12 when he and Patsy Kensit were on the cover of Vanity Fair as the coolest couple." In her autobiography, the "LDN" musician described an awkward situation that took place months later when Gallagher surprised her on the phone with Appleton. "Six months later I was in my car with my driver when the phone rang. . . It was Liam,' she wrote in her memoir. "He sounded awful, like he'd been up all night. 'Lil,' he said. 'I just need you to get on the phone. I've got Nic here. One of your mates is, like, trying to do a wind-up or something and saying that you and me had it off or whatever, and I need you to speak to Nic and say that it's all bollocks.'" Allen went on: "[I said,] 'Oh, Liam, yes sure, it's all bollocks. Let's say it's all bollocks - of course I'll tell Nicole that it's all bollocks if that's what you want - and not think about it too much or even at all, and then maybe it will go away and not disrupt what really matters: The people we love and rely on.'" Gallagher has never publicly commented on the allegations. Sam Cooper Lily Allen and Sam Cooper. Martin Grimes/FilmMagic Allen started dating builder and decorator Sam Cooper around the same time as her alleged hookup with Gallagher in July 2009. They announced they were expecting their first baby together in August 2010. After su