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 newspaper: “After Lily’s split from Ed, 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.”