Jennifer Aniston’s dating history (Picture: Getty Images)

Jennifer Aniston’s split from Justin Theroux is the latest in a long line of failed relationships for the actress.

While she has been married twice – once to Brad Pitt and once to Theroux – she was also once engaged to Tate Donovan, but they never made it up the aisle.

As Jennifer joins the Hollywood singles market once again (d’ya know who else is on that market right now? Brad Pitt, that’s who), we take a look back at her high profile romances.

Daniel McDonald

Jennifer Aniston pictured in 1990, when she was 21, at an NBC pool party in Los Angeles (Picture: Barry King/WireImage)

Credited with being Jennifer’s ‘first love’, TV actor and Broadway star Daniel McDonald dated the actress from 1990 to 1994.

Aniston recalled their relationship in a 2015 interview with the New York Times in which she described him as her soulmate but said he was an ‘unappreciated boyfriend”.

Daniel McDonald, pictured in 1997, died in 2007 (Picture: Walter McBride/Corbis via Getty Images)

‘He was my first love — five years we were together,’ she said. ‘He would have been the one. But I was 25, and I was stupid. He must have sent me Justin to make up for it all.’


Daniel tragically died in 2007 after being diagnosed with a brain tumour.

Tate Donovan

Tate Donovan and Jennifer Aniston at the New Amsterdam Theater in New York City, New York (Photo by Ron Galella, Ltd./WireImage)

Jennifer dated Friends guest star Tate Donovan, who played her crush Joshua, briefly in the mid-90s, with the pair becoming engaged in 1997.

However, sources later told the Daily Mail how Jennifer was still not over her romance with Daniel at the time.

‘Jennifer never stopped loving Daniel, but things were happening very fast with her career by that time – it was just a year before she landed Friends. She’d moved to Los Angeles, and Daniel stayed on in New York and was doing Broadway,’ the source said.

‘After Dan and Jen split, she went on to date and become engaged to actor Tate Donavan, but I don’t think she ever got over letting Dan slip through her fingers.’

Brad Pitt

CANNES, FRANCE – MAY 13: Actor Brad Pitt and wife actress Jennifer Aniston attend the World Premiere of the epic movie “Troy” at Le Palais de Festival on May 13, 2004 in Cannes, France. Aniston wears a dress by Versace. (Photo by Evan Agostini/Getty Images)

Jennifer and Brad started dating in 1998 and they married two years later on 29 July 2000 in a stunning Malibu wedding.

Their marriage lasted for four-and-a-half years, with the pair announcing their split on 7 January 2005. Their divorce was finalised on 2 October that year.

Brad was pictured with Angelina just three months after his split from Jennifer, with press speculation suggesting he had been unfaithful to Jen while filming Mr & Mrs Smith with Jolie. Both denied they had cheated.


Also at the time, it has been reported that they split due to Jennifer’s unwillingness to have children with Brad.

She told Vanity Fair that year: ‘I’ve never in my life said I didn’t want to have children. I did and I do and I will… I would never give up that experience for a career.’ She has also called called her and Brad’s relationship a ‘beautiful, complicated relationship.’

In a January 2015 interview with The Hollywood Reporter, she said of their break-up: ‘Nobody did anything wrong…. It was just like, sometimes things [happen].’

Vince Vaughn

(Picture: Clive Brunskill/Getty Images)

Jennifer dated her The Break-Up co-star Vince Vaughn from 2005 to 2006.

John Mayer

John Mayer and Jennifer Aniston in February 2009 (Picture: Kevin Mazur/VF/WireImage for Vanity Fair)

The Friends star had a brief romance with John Mayer too, dating him from 2008 to 2009.

Justin Theroux

Jennifer Aniston and Justin Theroux in February 2018 (Picture: Jordan Strauss/Invision/AP)

Jen and Justin met on the set of 2012 film Wanderlust and were together for seven years in total.

They became engaged in 2012 and wed in 2015 at their Bel Air home – the ceremony was apparently so low-key that their guests didn’t know they were attending a wedding.

They told friends that they were celebrating Justin’s upcoming birthday, but TMZ reported at the time that ‘the couple made the big reveal once all guests arrived…and Jen apologised for tricking everyone’.

The pair announced they had separated on 15 February.

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