Amy Winehouse’s Dating History Was Filled With Tumultuous Affairs Before Her Death at Age 27

Alex Clare

Amy was briefly linked to the British singer and songwriter in and around 2006, while she was on a break with then-boyfriend Blake Fielder-Civil, whom she’d later marry. When asked in a chat with uInterview what he remembers about his relationship with the late singer, he replied, “When I first heard Amy play a song on guitar — I was sitting alone with her in her apartment…she was just writing the album Back to Black. She played me a song, and I didn’t pick up a guitar or sing for like a month. I was like, ‘What is the point? How could you touch that?’ She blew me away so much. She was an incredibly gifted person, but like a lot of incredibly gifted people, they come with baggage, and she didn’t have the ability to deal with it in a healthy way.” However, things didn’t seem to end well between the two. Alex sold a story about their sex life to the tabloid News of the World, which ran it with the headline “Bondage Crazed Amy Just Can’t Beehive in Bed.”

Blake Fielder-Civil

Amy was married once before her death at 27 years old in 2011. She and the former video production assistant had a tumultuous, on-off relationship over the years but made things official when they tied the knot in Miami in May 2007. However, their marriage ended in divorce in 2009, as their relationship appeared to be extremely toxic. In a 2023 interview with Good Morning Britain, Blake addressed claims and suggestions that he was the reason Amy died of an accidental alcohol overdose at such a young age. “I’ve needed to stop carrying that cross on my own. I’ve carried that burden myself for over 10 years. I feel, to be honest, that I’m the only person within that story that’s ever held any accountability, that’s ever tried to say, ‘Yep, I made some huge mistakes,'” he said. “I was a 20-something-year-old drug addict. So I had absolutely no idea how to make myself clean, let alone somebody else who was a big cog in a machine for a record label, and there were vested interests in Amy carrying on performing.”

Pete Doherty

Though it was merely rumored that Amy dated the cofrontman of The Libertines when she was alive, Pete later opened up about their relationship in a 2012 interview with The Daily Mail. “This is difficult for me to admit,” he said. “But, yes, it’s true. Amy and I were lovers. I loved her then and, well, I still do today. But towards the end, as only lovers can, she became quite mean and cruel to me. She didn’t suffer fools…and believe me, she had a mean right hook.” The two were often spotted out and about together at nightclubs and parties, but the relationship eventually came to an end.

Reg Traviss

Amy was linked to the British writer and film director from early 2010 until her death. According to Digital Spy, the late star’s father told The Sun he believed the pair would marry and have children. “When Reg came on the scene, he was a breath of fresh air. I believe they would have married,” he said. “She wanted to have children and what nicer person to have them with than Reg. His manners are from a bygone era. He looked like my dad in the 1940s. It is so sad they never had the life they planned.” Shortly after Amy’s death, Reg said in an interview (per Us Weekly), “The last three days have been hell. I want to thank all those who are mourning the loss of Amy — such a beautiful, brilliant person and my dear love.”

Kristian Marr and Chris Taylor

Kristian, an English actor and musician, was primarily just a close friend of Amy’s; however, he later admitted in a 2011 interview with The Mirror that they did get intimate. “We swapped numbers and very quickly fell into a weirdly close relationship. She had a boyfriend and I was still seeing Sadie (Frost) so we just became best friends,” he said. “We’d always had a very close relationship but because of my girlfriends and her boyfriends it had never gone further. Then when we were both single for a few weeks last summer I went round and we just ended up in bed. We talked about it later and decided our friendship was too special and we should go back to that.”

And while details are scarce, it’s been widely reported that Chris and Amy previously dated and that her song “Stronger Than Me” from her debut album Frank is about him. He is played by Ryan O’Doherty in the biopic.

Josh Bowman

In 2009, Amy was briefly involved with the British actor, whom she reportedly met while vacationing on the island of St. Lucia. While their affair was short-lived, according to The Daily Mail, the singer was smitten after meeting Josh. “I love it here and have never felt so happy,” she said of being in the Caribbean with the actor. “In fact, I don’t think I’m ever going home. Especially as I met Josh here. He couldn’t be more different from my husband, which isn’t a bad thing.” Years later, Josh was asked during an interview with GQ about his relationship with Amy, to which he simply replied, “Yeah…I’m not really ready to talk about that.”