Jennifer Aniston
Pitt met Aniston in 1998, proposed in 1999, and married a year later in 2000. The wedding was the event of the year with four bands, over 200 guests, a gospel choir, 50,000 flowers, and fireworks. Sadly, just five years later, they announced their breakup and filed for divorce in March 2005. After he broke up with Angelina Jolie, it was reported that the two texted once in a while and that he came to her birthday party in 2019, but insiders confirmed they’re not looking to get back together.
Angelina Jolie
These two met on the set of Mr. & Mrs. Smith in 2003 but didn’t start dating right away, especially as Pitt was still with Aniston. However, the two couldn’t deny their romance by the end of the film. Pitt and Aniston split in 2005, and by 2006, Zahara and Maddox changed their last names to Jolie-Pitt. The same month, Jolie announced she was pregnant with Shiloh. They then adopted Pax Thien, and in 2008, Angie was pregnant again. The couple made it official by marrying in 2014 after being urged by their kids, but in 2016, after just two years of marriage, they went through an ugly divorce following a heated fight on a private plane that evidently turned physical. Negotiations spanned five years, and their legal battle over their winery continues to this day.
Ines de Ramon
After Pitt and Jolie broke up, the actor was rumored to be dating several women, including Alia Shawkat, Sat Hari Khalsa, and Neri Oxman. The only one that stuck was his relationship with Ines de Ramon, a jewelry company executive he was first connected to in November 2022 after being spotted at a Bono concert in LA together. Public knowledge revealed that she moved into his home in 2024, the same year they made their red carpet debut together.
