Jennifer Aniston's romantic history

Tears for Matthew Perry
Matty, I love you so much
Romance with Matthew Perry?
Tate Donovan (1995)
Brad Pitt (1998)
Seven years of happiness
Shocking: Jennifer Aniston and Brad Pitt's separation
Vince Vaughn (2006)
John Mayer (2008)
Gerard Butler (2010)
Justin Theroux (2011)
Justin and Aniston's failed marriage
Chris McMillan, 'the man of her life'
Ross. Always Ross.
Tears for Matthew Perry

Jennifer Aniston got genuinely emotional when she was asked about 'Friends' in the Variety segment 'Actors on Actors'. The video of the famous actress crying and tapping her eyes with a tissue went viral in early June 2024. "I'm sorry, she said, "I just started thinking about –" And most viewers figures she referred to Matthew Perry, her buddy from 'Friends' who suddenly died in late 2023.

Matty, I love you so much

The actress who played Rachel in 'Friends' explained that the six actors of the show are "a family forever." About Matthew Perry she wrote on Instagram right after his death: "He was such a part of our DNA... Matty, I love you so much and I know you are now completely at peace and out of any pain. I talk to you every day..."

Romance with Matthew Perry?

Was there more between the two actors? People say (but never confirmed) that Jennifer Aniston and Matthew Perry had a brief romance in 2005, after 'Friends' had ended. No one would have imagined Chandler and Rachel together on the show, but it may have happened in real life.

Tate Donovan (1995)

If we look at Jennifer Aniston's confirmed romantic history, Tate Donavan is there. They were steady for over three years, from 1995 to 1998. Curiously, the couple broke up days before the actor had a role in the series as Rachel's boyfriend! That must have been awkward!

Brad Pitt (1998)

Before she'd started seeing Tate Donovan, Jennifer Aniston had already met Brad Pitt. It was 1994, People magazine recounts, and they didn't get romantically involved at the time. However, in 1998, the time was right for one of the It Couples of the 90s and 2000s!

Seven years of happiness

For seven years, Brad and Jennifer were among the most famous couples in the world. They married in the summer of 2000 in Malibu, while each of them enjoyed a high point in their career. The couple would even style the same way whenever they walked a red carpet.

Shocking: Jennifer Aniston and Brad Pitt's separation

But then came 2005, and Brad Pitt shot 'Mr & Mrs Smith' with Angelina Jolie. No one would have suspected Pitt to leave Jennifer for someone else, especially when they saw him looking at her this way during the Primetime Emmys in 2004.

Have a look at these photos if you want to see more of Jennifer and Brad's iconic love story

Vince Vaughn (2006)

It took Jennifer Aniston a year to fall in love again after she separated from Brad Pitt. She got to know Vince Vaughn on the set of 'The Break Up'. While they had a similar sense of humor and must have had a lot of laughs together, the relationship lasted only a year.

John Mayer (2008)

This Casanova is the subject of Taylor Swift's song 'Dear John,' and he also dated Jennifer Aniston at some point. They met at an Oscar afterparty in 2008 and dated for about a year. .

Gerard Butler (2010)

On the set of their film 'The Bounty Hunter', Jennifer Aniston and Gerard Butler hit it off. However, they didn't last much longer than the time it took to shoot the film and promote it.

Justin Theroux (2011)

After these brief romances, Justin Theroux appeared as a new, serious partner for Jennifer Aniston. He was handsome, friendly, and had a skin that, according to Jennifer, was smoother than her own. The two met in 2007 and became romantically involved in 2011, People magazine reports.

Justin and Aniston's failed marriage

They married in the summer of 2015, but two and a half years later they suddenly announced their divorce. No one knows what happened, but fans and media soon began to speculate about a new life for the Aniston-Pitt relationship, as Brad Pitt had separated from Angelina Jolie in 2016.

Chris McMillan, 'the man of her life'

It may not have been a romantic relationship, but it's definitely been stable. Chris McMillan is Jennifer Aniston's hair stylist, close friend, and business partner. What's more, McMillan 'invented' the hairdo that is known as the 'Rachel Hairstyle', which someday will become a UNESCO cultural heritage.

Ross. Always Ross.

Having seen all of Jennifer Aniston's wonderful boyfriends and husbands, we must say that none of them has been as worthy of the actress's love (real or fictional) as David Schwimmer. For a series to completely change its plot and maintain it for 10 seasons based on the chemistry of two actors is incredible, and it happened with Ross and Rachel. Let no one ever forget it.

Follow Showbizz Daily to see the best photo galleries every day

More for you