Lily Allen’s Complete Dating Timeline, From David Harbour to Rupert Grint
Lily Allen has recently been under the spotlight, with a flurry of attention around her past relationships and the ups and downs of her marriage with David Harbour. Despite her reputation as a bold and quirky music artist known for hits like “The Fear” and “Not Fair,” her personal life has also been quite eventful.
Before tying the knot with Harbour, Allen was previously married to Sam Cooper, with whom she shares two children. However, her romantic history is filled with intriguing escapades, including rumored relationships with DJs and even gossip about a possible romance with Harry Potter star Rupert Grint. Regrettably, Allen has also been open about struggles with infidelity in past relationships.
To unravel the full saga, let’s rewind the clock by two decades and delve into Lily Allen’s entire dating timeline:
Seb Chew (2005-2007)
Allen dated Seb Chew from 2005 to 2007 before moving on to a relationship with Chemical Brothers DJ Ed Simons. Although details about her relationship with Chew remain sparse, she confirmed their breakup during the GQ Awards in London, where she expressed her status as a single woman. Interestingly, the two reconnected a decade later, with Chew co-producing two of Allen’s albums, No Shame (2018) and West End Girl (2025).
Ed Simons (2007-2008)
Following her split from Chew, Allen began dating Ed Simons in 2007, reportedly introduced to him through mutual friends. Their relationship took a significant turn when they revealed they were expecting a child, only to face the heartbreaking loss of a miscarriage. The pair parted ways shortly after this traumatic event. Allen also shared insights into the aftermath, highlighting the complexities and emotional challenges they navigated, despite maintaining a cordial friendship.
Rupert Grint (2008)
In the aftermath of her breakup with Simons, Allen found solace in a friendship with Rupert Grint in 2008. Their companionship blossomed after connecting at the premiere of Order of the Phoenix, leading to shared meals at various London eateries. While rumors of a budding romance swirled around them, sources clarified that their relationship was rooted in friendship. Grint’s supportive presence and ability to make Allen laugh contributed to their close bond and public outings.
Wade Oates (2008)