Entertainment

Brad Pitt's Dating History: 15 Surprising & Unforgettable Romances

EntertainmentPublished Apr 26, 2018
By Kayla Boyd
brad pittMario Anzuoni/Reuters/Splash

When it comes to Hollywood, there are certain questions people can't help but ask -- like what's up with the hot celeb guys named Chris? And who is Brad Pitt dating? This Hollywood heartthrob has been in the public eyes for many years, which means his relationships have, too. Although fans know all the details about Brad Pitt and his marriages to Angelina Jolie and Jennifer Aniston, he actually did quite a bit of dating in his former years (think '80s and '90s). And some of the women he's reportedly been with might cause a shock!

Brad Pitt's dating history shows that he has had his fair share of costar romances, one-off dates (including a somewhat long list of singers, actresses, and models, possibly even a professor), and many serious relationships that led up to engagements -- four of them to be exact! And though the status of his relationships isn't always clear, we know that Brad does not exactly have a lot of trouble when it comes to finding someone new to spend his time with.

The famous single dad of six has always been a good-looking guy, with many of his exes calling him sweet and nice. (After all, he is Brad Pitt.) This man has definitely had a lot of love in his life, so here is a guide to Brad Pitt's complicated dating history.

1/15
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Sinitta
James Higgins/Splash News

Sinitta

Brad dated singer Sinitta on and off from 1984 to 1986. Sinitta once confessed in an interview, "[Brad] was fun, he was young and very sweet."

2/15
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Robin Givens
Vinnie Zuffante/Getty Images

Robin Givens

Brad also had a fling with Robin Givens in the '80s as well. The pair posed for this picture together in 1989, but they were apparently seeing each other well before then. It was pretty big celebrity scandal because of the rumored overlap with his relationship with Sinitta. (Robin was married to Mike Tyson at the time.) The boxer once said in an interview that he caught Brad and Robin together at her house, but he didn't care because they were already getting divorced, and Brad's "a really nice guy."

Wow!

3/15
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Shalane McCall
Ron Galella, Ltd./Getty Images

Shalane McCall

Brad played Shalane McCall's boyfriend on a few episodes of Dallas between 1987 and 1988. They were rumored to have had an off-camera romance during that time.

4/15
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Jill Schoelen
Ron Galella, Ltd./Getty Images

Jill Schoelen

Brad met Jill Schoelen on the set of Cutting Class. She became his first fiancée after he proposed to her back in 1989. They were only engaged for three months before Jill dumped him.

5/15
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Christina Applegate
Barry King/Getty Images

Christina Applegate

Actress Christina Applegate took Brad as her date to the MTV Movie Awards in 1989. However, she reportedly ditched him halfway through the night to hang out with another guy! (Talk about a celebrity tragedy!)

6/15
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E.G. Daily
Barry King/Getty Images

E.G. Daily

This photo from 1989 captured Brad and E.G. Daily when they were briefly dated. For those who might be scratching their heads, E.G. Daily is likely best known as the voice of Tommy Pickles in Rugrats. (She also had a guest role on Friends.)

7/15
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Juliette Lewis
Ron Galella, Ltd./Getty Images

Juliette Lewis

Brad dated his Too Young to Die? and Kalifornia costar Juliette Lewis from 1989-1993. At the time when they first got together, Brad was 27 and Juliette was 17.

8/15
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Geena Davis
Thelma & Louise/IMDb

Geena Davis

The '90s heartthrob's career really took off in 1991, thanks to Thelma & Louise. And apparently, the film led to an unexpected romance, too. Brad and costar Geena Davis were rumored to have had a fling when cameras weren't rolling.

9/15
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Thandie Newton
Splash News

Thandie Newton

In 1994, Brad and Thandie Newton dated for a short time after meeting on the set of Interview With the Vampire.

10/15
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Jitka Pohlodek
Ron Galella, Ltd./Getty Images

Jitka Pohlodek

It was only a matter of time before a celebrity model made this list. Jitka Pohlodek was Brad Pitt's date to the 1994 premiere of Legends of the Fall, but nothing seemed to come of it.

11/15
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Gwyneth Paltrow
Kevin Mazur Archive/WireImage/Getty Images

Gwyneth Paltrow

Brad started dating actress Gwyneth Paltrow after meeting her on the set of Se7en. He proposed to her in 1997 after three years of dating, but the engagement was called off seven months later.

(Seven. Full circle.)

12/15
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Claire Forlani
Ron Galella, Ltd./Getty Images

Claire Forlani

After his breakup with Gwyneth, Brad reportedly dated his Meet Joe Black costar Claire Forlani for a brief time. The couple attended the 50th Annual WGA Awards together.

13/15
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Jennifer Aniston
Ronald Asadorian/Splash News

Jennifer Aniston

Cue the Brad Pitt and Jennifer Aniston pause. The couple met on a blind date, and after two years of dating, they got engaged -- with Jen becoming his first wife in July 2001. Trouble, however, came along a few years later when Brad met Angelina Jolie while filming Mr & Mrs Smith, leading to Brannifer announcing their divorce in January 2005.

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Angelina Jolie
Splash News

Angelina Jolie

Brad and Angie news alert! "Brangelina" became a thing shortly after Brad's split with Jen -- resulting in 12 years of togetherness, including two years of marriage -- before Angelina filed for divorce in September 2016. They have six kids together: Maddox, 16; Pax, 14; Zahara, 13; Shiloh, 11; and twins Knox and Vivienne, 9.

15/15
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Neri Oxman
Jacopo Raule/Getty Images

Neri Oxman

Since his split with Angelina Jolie, Brad is reportedly dating Neri Oxman, an MIT professor, architect, and designer. While the pair have yet to confirm their possible relationship, sources claim Brad and Neri's chemistry is "off the charts."

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