Jennifer Aniston and Angelina Jolie were known for being part of Brad Pitt’s romantic life. Recently, Pitt and Aniston sent the internet ablaze with their heartfelt reunion at the SAG Awards and also during their star-studded table read of Fast Times at Ridgemont High. 

Meanwhile when it comes to Pitt and Jolie, they have been on the cover of magazines since their Mr. and Mrs. Smith days up until their more recent divorce and custody battle. Pitt has also dated other A-listers such as Gwyneth Paltrow.

The couple dated from 1994 to 1997. Pitt and Paltrow’s relationship started on the set of 1995’s Se7en. E Online reported that the actor thanked Paltrow and called her his “angel” and the “love of [his] life” after winning the Golden Globe for 12 Monkeys. The actor then proposed and the pair were engaged briefly before they split up. Since then, Paltrow has explained the reasons that led to their split, placing most of the blame on herself.

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According to Entertainment Tonight, Paltrow opened up about her relationship with Pitt during an interview with Howard Stern. She shared about falling in love with Pitt but that love is not enough.

She stated, “I definitely fell in love with him. He was so gorgeous and sweet. I mean he was Brad Pitt.”

When asked to explain how she figured out it wasn’t meant to be, how “you find you’re not right for each other,” she replied:

“I was such a kid. I was 22 when we met. And, it’s taken me until like 40 to get my head out of my ass. I wasn’t ready, and you know, he was too good for me.”

Brad Pitt and Gwyneth Paltrow were engaged for a short while. Picture: YouTube

The duo had a decent age difference, with Pitt being eight years older than Paltrow. Eight years means people are in different life stages when it comes to people in their 20s and 30s. Paltrow said that she had to work some stuff out on a personal level before settling down. Her father was also devastated when his daughter broke up with Pitt.

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“My father was so devastated when we broke up. My father loved him like a son,” said Paltrow.

After Pitt, Paltrow dated Ben Affleck. In 2003, she married Coldplay’s frontman Chris Martin and they remained married until 2016.  Today, Paltrow is married to Brad Falchuk — a director, writer, and producer who co-created Glee, Pose, and American Horror Story with Ryan Murphy.