Once Upon a Time&nbsp;in&nbsp;Brad Pitt's life, he dated...&nbsp;

One of the biggest <a href="https://www.lofficielusa.com/pop-culture/ultimate-celebrity-heartthrobs-by-decade-brad-pitt-harry-styles" target="_blank" rel="noopener">heartthrobs</a> of the '90s, Brad Pitt&nbsp;is famous for his roles in films, including Thelma &amp; Louise, <a href="https://www.lofficielusa.com/film-tv/margot-robbie-movies-film-wolf-of-wall-street-barbie-bombshell" target="_blank" rel="noopener">Once Upon a Time in...Hollywood</a>,&nbsp;and&nbsp;Ocean's Eleven, landing him a spot amongst the top actors in Hollywood. With news of his upcoming film <a href="https://www.imdb.com/title/tt14257582/">Wolfs</a>,&nbsp;L'OFFICIEL decided to take a look back at the A-list actor's dating history. We're here to break down his first engagement, his fourth engagement, and everything in between.&nbsp;

The British singer and Pitt dated for around two years in the late '80s. And years later, after they had both gotten married and then divorced, the singer said Pitt reached out to her. "He has been calling and you know what I said? 'Brad. Move on,'" she <a href="https://www.dailymail.co.uk/tvshowbiz/article-4071220/Sinitta-insists-newly-single-ex-boyfriend-Brad-Pitt-wants-reignite-love-admits-s-good-kisser.html" target="_blank" rel="noopener">revealed</a> during Alan Carr's New Year Spectacular in 2016.&nbsp;

Long before Pitt was married to <a href="https://www.lofficielusa.com/pop-culture/young-jennifer-aniston-sexy-photos-brad-pitt" target="_blank" rel="noopener">Jennifer Aniston</a>, and later, Angelina Jolie, Pitt envisioned his future with someone else. Pitt met Jill Schoeleon on the set of Cutting Class,&nbsp;and ended up getting engaged. But in 1989, after only three short months, Schoelen dropped him for a <a href="https://www.cosmopolitan.com/uk/entertainment/news/a46136/brad-pitt-dating-girlfriends-timeline/#:~:text=Jill%20Schoelen%2C%201989.,Burn%20Part%20II." target="_blank" rel="noopener">movie director.</a>&nbsp;

The two <a href="https://www.instyle.com/news/tbt-brad-pitt-juliette-lewis-relationship" target="_blank" rel="noopener">reportedly</a> met on set of&nbsp;Too Young to Die?, the film. And before ultimately calling it quits, the couple lived together for three years and worked on multiple projects together.&nbsp;

A secret girlfriend? According to Jason Priestley in a&nbsp;<a href="https://www.hollywoodreporter.com/lifestyle/lifestyle-news/jason-priestley-dishes-shannen-dohertys-702045/" target="_blank" rel="noopener">The Hollywood Reporter</a>&nbsp;interview, Davis and Pitt kept their romance from the public eye. The interview notes, "He also remembers Pitt sneaking off to visit his secret girlfriend, Geena Davis, after&nbsp;Thelma&nbsp;wrapped, noting that the far more famous actress refused to visit Pitt&rsquo;s frat-like West Hollywood duplex." We'll just leave that here.&nbsp;

Getty

Next up: one of the most iconic blonde-haired couples of the '90s. <a href="https://www.lofficielusa.com/fashion/gwyneth-paltrow-young-best-90s-style" target="_blank" rel="noopener">Gwyneth Paltrow</a> and Brad Pitt began dating in <a href="https://www.usmagazine.com/celebrity-news/pictures/gwyneth-paltrow-and-brad-pitts-relationship-timeline/they-met-on-the-set-of-se7en/" target="_blank" rel="noopener">1994</a> after meeting on the set of&nbsp;Se7en. Two years later, the two took the next step and got engaged. But not long after, in 1997, the pair had finally called it quits for good. Despite their split, the two still have love for each other. 
In a 2022 <a href="https://goop.com/style/outfitting-ideas/gwyneth-paltrow-brad-pitt-interview/" target="_blank" rel="noopener">Goop</a>&nbsp;interview, <a href="https://www.lofficielusa.com/pop-culture/gwyneth-patrow-body-image-aging-self-acceptance-process" target="_blank" rel="noopener">Paltrow</a> asked Pitt what kind of impact her father had on him while tossing in a reference to their past relationship. She said, "What impact did he have on you? Why did you love him, even though we didn&rsquo;t get married, unfortunately." Pitt replied, "<span style="background-color: transparent; font-family: inherit; font-size: inherit; font-style: inherit; font-variant-ligatures: inherit; font-variant-caps: inherit; font-weight: inherit; letter-spacing: 0px;">Yeah, right. <span style="background-color: transparent; font-family: inherit; font-size: inherit; font-style: inherit; font-variant-ligatures: inherit; font-variant-caps: inherit; font-weight: inherit; letter-spacing: 0px;">Oh man, everything works out, doesn&rsquo;t it?" 
<span style="background-color: transparent; font-family: inherit; font-size: inherit; font-style: inherit; font-variant-ligatures: inherit; font-variant-caps: inherit; font-weight: inherit; letter-spacing: 0px;">Paltrow responded, joking about her current marriage to Brad Falchuk, "Yes, it does. I finally found the Brad I was supposed to marry. It just took me 20 years."

What started as a beautiful romance ended in one of the world's most well-known <a href="https://www.lofficielusa.com/pop-culture/celebrity-love-triangles-justin-bieber-selena-gomez-hailey-bieber-kardashian-jenner" target="_blank" rel="noopener">love triangles</a>. Brad Pitt and <a href="https://www.lofficielusa.com/pop-culture/young-jennifer-aniston-sexy-photos-brad-pitt" target="_blank" rel="noopener">Jennifer Aniston</a> first began dating in 1998 after being set up by...wait for it...their <a href="https://www.marieclaire.com/celebrity/g18655293/brad-pitt-jennifer-aniston-relationship-timeline/" target="_blank" rel="noopener">agents.</a> And in July of 2000, the iconic duo tied the knot. After a few years of wedded bliss, the two announced in 2005 that they were separating.&nbsp;
Their statement to <a href="https://people.com/archive/cover-story-heartbreaker-vol-63-no-3/" target="_blank" rel="noopener">People</a> read: "<span style="background-color: transparent; font-family: inherit; font-size: inherit; font-style: inherit; font-variant-ligatures: inherit; font-variant-caps: inherit; font-weight: inherit; letter-spacing: 0px;">We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months."

Mr. and Mrs. Smith or Mr. and Mrs. Pitt? Spoiler: they get there eventually. Pitt and <a href="https://www.lofficielusa.com/film-tv/angelina-jolie-directing-without-blood-film-salma-hayek" target="_blank" rel="noopener">Jolie</a> met <a href="https://www.glamour.com/gallery/brad-pitt-and-angelina-jolie-relationship-photos" target="_blank" rel="noopener">on set</a> of the former in 2004. After 10 (yes, 10!) years of being a couple, some red carpet appearances, and welcoming children into the world&mdash;the couple shares six children&mdash;the two finally <a href="https://www.glamour.com/story/brad-pitt-angelina-jolie-married" target="_blank" rel="noopener">tied the knot</a> in 2014. Two short years later, in 2016, Jolie filed for <a href="https://people.com/movies/angelina-jolie-and-brad-pitt-to-divorce/" target="_blank" rel="noopener">divorce</a>.
The former couple has been dealing with many legal battles ever since. The most recent feud was in February over a $500 million French vineyard, Ch&acirc;teau Miraval, that they owned together.&nbsp;Jolie and Pitt have also been immersed in an ongoing custody battle over their six children&mdash;Maddox, Zahara, Shiloh, Pax, Knox, and Vivienne.&nbsp;

Nicole Poturalski

In August of 2020, <a href="https://pagesix.com/2020/08/26/brad-pitt-and-german-model-nicole-poturalskis-relationship-confirmed/" target="_blank" rel="noopener">Page Six</a>&nbsp;reported that the Fight Club actor was seeing <a href="https://www.lofficielusa.com/fashion/highest-paid-models-in-the-world-kendall-jenner-gisele-bundchen" target="_blank" rel="noopener">model</a> Nicole Poturalski. However, not much is known about their lowkey relationship. The two were <a href="https://pagesix.com/2020/08/26/brad-pitt-and-german-model-nicole-poturalskis-relationship-confirmed/" target="_blank" rel="noopener">photographed</a> together in 2019 but reportedly had <a href="https://pagesix.com/2020/10/28/brad-pitt-and-girlfriend-nicole-poturalski-break-up/" target="_blank" rel="noopener">split</a> by October 2020.

After being spotted together at a Bono concert on November 13, a source revealed to <a href="https://people.com/movies/brad-pitt-ines-de-ramon-have-been-dating-for-a-few-months-exclusive/" target="_blank" rel="noopener">People</a> in 2022 that Pitt and Ines de Ramon "have been dating for a few months." The insider explained, "They met through a mutual friend. She is very nice," and that "Brad is really into" her. De Ramon currently works for the jewelry brand Anita Ko. 
The couple have been seen in public together ever since de Ramon separated from The Vampire Diaries&nbsp;star Paul Wesley in 2022, and they've been inseparable ever since. Their most recent outting was in December 2023 at Pitt's 60th birthday celebration in Los Angeles. Currently, sources say the couple is trying to keep things more private in an effort to protect and respect their yearlong relationship.&nbsp;&nbsp;

Brad Pitt's Complete Dating History

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