Lily’s personal life hasn’t been as smooth as her professional life and her ups and downs have affected her mentally and physically too. Her first reported boyfriend was record company executive Seb Chew who she had reportedly met while being in the music circuit. They supposedly started dating in 2005 when Lily was just about 20 years old. Seb was much older but their romance is said to have been quite good till it lasted. Rumors had even spread that Lily had taken the easy route of taking the help of her partner to make it big into the music industry. On an ironical note, some websites cited that it was Seb who had chosen to become famous by dating Lily Allen. But those were mere rumors that gossip circles enjoyed till Lily eventually broke up in January 2007, hence ending a 3 year old relation.

She was quiet in her personal life for a while before she started dating the Chemical Brothers singer, Ed Simons in September 2007 after a short meet up at some event. This affair led to quite a few controversies but the initial period was quite sweet and smooth to the media. Lily was soon pregnant with Ed’s baby but they split almost immediately after she has a miscarriage that she reported, led her into severe depression and trauma. She spent quite a few weeks at the psychiatrist before restarting her music career and eventually moving on.

She reportedly started dating actor Rupert Grint famous for playing the role of Ron Weaseley in the widely acclaimed Harry Potter Series. This was an apparent change from Lily’s usual choice of partners and people had started to take the relation quite seriously before it was found that those were mere rumors and that Rupert was dating someone else. The rumors mostly surfaced where camera caught them together at the movie premiere and Lily’s heartbreak only fueled the process.

Lily’s next relationship, which is subsequently also her last, started with builder Sam Cooper in August 2009 and very little is known about how the two met while friend circles have suggested they met-up through a group of mutual friends and they hit off instantly. She had another miscarriage with Sam before he married her on Christmas, 2010. Lily was reported as calling it the happiest day of her life. She has had two healthy babies since then with the only exception of one stillborn in between. Lily took a long break to concentrate on acting but has been back to music since 2013 much to her fan’s delight. Whatever might be the case, one would want this happy couple to be out of any divorce.