Inside Brad Pitt’s Epic Dating History

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Brad Pitt is often recognized for showing off his physique on the big screen, yet he typically prefers to maintain privacy when it comes to his private life.

Or he tries, but sometimes it’s simply enjoyable to join your significant other out in public.

Despite his tumultuous love life often making tabloid news, Brad generally prefers to lead a peaceful, private existence whenever he can, given that he has married and divorced two globally recognized personalities.

16 months ago, he confided in Ines de Ramon what he had been keeping to himself. Only later did they start appearing at events where photographers were present, such as last summer’s British Grand Prix and the 2024 Venice International Film Festival, marking their first red carpet appearance together.

Ines isn’t a stranger to this world, as she had been married to Paul Wesley from “The Vampire Diaries” for three years prior to their separation in 2022 (the divorce was finalized in March 2024, which was nine months before Brad and Angelina Jolie officially ended their relationship after eight years together).

By the way, this is a significant change in Brad’s detailed chronology of relationships, marking the first update since his separation from Angelina in 2016.

For over four decades, he, now 61 years old, has encountered numerous women due to his stardom. Many of these women became more than just acquaintances and went on to have memorable relationships with him.

To celebrate Brad’s recent milestone on life’s journey, we are presenting to him a collection of his notable romantic relationships. Though it may not be as extensive as his film career, it carries its own grandeur:

1. Jennifer Aniston (1998-2005)
2. Angelina Jolie (2005-2016)
3. Irina Shayk (2015-2019)
4. Gwyneth Paltrow (1997-1999)
5. Sinitta Malone (1988-1992)

This timeline provides a glimpse into Brad’s romantic history, showcasing the significant women who have graced his life throughout the years.

Since Ines accompanied Brad to several F1 events this year, such as the New York premiere of the action drama on June 16.

However, in the world of Hollywood, they maintained an air of nonchalance, while their relationship blossomed secretly and passionately behind the veil.

Back in the swanky circle of an Oscar-winning legend last November 2022, I found myself, and come the following August, I was casually flaunting a chic “B” pendant necklace around my neck – subtly hinting at a possible bond that’s brewing.

Last year’s date nights kept recurring, and when they attended the British Grand Prix, it was like a starting flag had been waved – they were in for an exciting ride ever since.

I must say, it’s been quite some time since there’s been a significant change in my personal chronicle since my separation from Angelina back in 2016. This is a new chapter, however.

For over four decades, this 61-year-old individual has been a well-known figure, and as a result, he’s encountered numerous women. Many of these women became his romantic partners, and a good number of them still recall him warmly.

To celebrate Brad completing another lap on life’s track, we are presenting him with a collection of his romantic past. Although it may not be as extensive as his film career, it’s no less extraordinary:

In the 80s, the singer known as “Toy Boy” dated Brad Pitt for several years. This was before every couple had a unique, single-word nickname. When asked in 2016 what their affectionate name could have been, the pop star playfully suggested “Braditta.

As a lifestyle connoisseur, I’d like to share an intriguing piece of Hollywood history. In the late ’80s, I found myself playing the on-screen love interest of a captivating actress on the iconic series, “Dallas.” My character was Randy, and our bond extended beyond the script, sparking off-camera rumors that fueled the public’s curiosity. However, fate had different plans for her. In 1989, she exchanged vows with Trent Valladares, a union that has endured to this day. At just 17, she made the decision to walk down the aisle and never looked back.

Pitt’s first betrothed was Schoelen, his co-star in “Cutting Class”. They were engaged for three months when Schoelen, feeling lonely while shooting a movie in Budapest, asked Pitt to visit her there. Pitt reportedly shared with The Sun in 2011 that he spent $600 of his $800 savings on a ticket from Los Angeles to Hungary. Upon arrival, he went directly to the set where she was filming and they had dinner that night. However, Schoelen confessed her affection for the film’s director, leaving Pitt stunned. He responded, “I’m outta here.” Love indeed is full of surprises!

In January 1989, Pitt made an appearance on the actress from Riverdale’s sitcom titled Head of the Class. By February, Robin Givens’ divorce papers with Mike Tyson weren’t even dry yet. Later, Tyson recounted an encounter with Pitt who was smoking marijuana, when he unexpectedly found him at his then-wife’s house one morning. Tyson claimed that he had intended to have a brief visit while on his way to meet his divorce attorney.

He mentioned during his story on Conan in 2012, “She pulled up with the dashing Brad Pitt,” he said. In one of his anecdotes from his one-man show, Andy Richter commented, “Brad Pitt stands for that worldwide, you know, symbol.

Over the years, this story remained a preferred topic among interviewers, with Tyson wrapping up on The Real in 2016, stating, “I didn’t actually catch him in the deed – perhaps before it happened… He’s truly a kind individual.

At the 1989 MTV Video Music Awards, Pitt was accompanied as a date by the star of “Married…With Children”. Although she has remained silent on the matter, Sebastian Bach, the rocker from Skid Row, claims that he was the man whom Applegate famously left her rising actor date for that evening.

Pitt was romantically involved with Dottie from the film ‘Pee-Wee’s Big Adventure’ back in 1989. Contrary to his rebellious image, Dailly would later characterize him as a “relaxed, very down-to-earth” individual who wasn’t overly enamored with Hollywood glitz. She stated that he was the kind of man who would spontaneously depart and drive off in his car just to escape the city, sharing this insight with DailyMail.com in 2016.

In 1991, Brad Pitt astonished Julie Davis on the big screen by playing a cunning hitchhiker in “Thelma & Louise.” This film was a significant milestone for both Pitt and his physique, marking their debut into stardom. Interestingly, Brad Pitt’s former roommate, Jason Priestley, revealed in his 2014 memoir that they were involved romantically off-screen as well.

Davis reminisced to The Hollywood Reporter in 2014 about his initial reading with Pitt for the role; there were five contenders initially. However, when Pitt arrived, things became a bit awkward—Davis admitted he got distracted during the scene and found himself struggling with his lines. He jokingly said, “I was messing up this kid’s audition big time.

They portrayed troubled couples on screen twice, first in the 1990 TV movie “Too Young to Die?” and later in the 1993 thriller “Kalifornia”. However, it appears that their real-life relationship was more harmonious, as he accompanied her as her date at the Oscars in 1992 when she was nominated for “Cape Fear”, and they were together for several years.

Brad Pitt expressed his continued affection for the woman in an interview with Vanity Fair in February 1995. He admired her intelligence, saying it was a wonderful experience being with her. He described their relationship as one of the best he’s ever had. However, he acknowledged that love doesn’t always conquer all. In 2010, Lewis stated that she and Pitt occasionally bump into each other and exchanged pleasantries, which she found nice.

Pitt recounted his time working on the film “Interview With the Vampire” as an unpleasant experience. In 2011, he shared with Entertainment Weekly that “the positive outcome of that movie was it sparked my romance for New Orleans.

However, the event also sparked a fleeting romance between Newton and Pitt, where Newton took on a minor role as Yvette, a servant at Louis’ plantation.

Or:

But this incident led to a short-lived liaison between Newton and Pitt, with Newton acting in a secondary role as Yvette, who worked as a servant at Louis’ estate.

At the 1994 red carpet premiere of “Legends of the Fall,” I was the fortunate companion of Brad Pitt, a role that undeniably boosted his heartthrob appeal. During our relationship, when Brad confided in Vanity Fair that he continued to harbor feelings for Juliette Lewis, it only served to heighten the intrigue surrounding his personal life.

In 1995, it was Pitt who became smitten with Paltrow during the filming of “Se7en”. From her slip dress to the ends of his frosted hairdo, they were a prominent couple from the mid-90s. Brad received the Best Supporting Actor Golden Globe for “12 Monkeys” in 1996 and thanked Gwyneth, calling her his “angel, my life’s love”. He proposed to her that same year, and at one point, they even sported matching hairstyles.

Gwyneth emphatically expressed to Entertainment Tonight that she regards the institution [marriage] deeply and personally, as there has never been a divorce in her or her partner’s family – a fact that underscores their long-standing relationship, which makes this decision neither hasty nor impulsive. However, it’s important to note that they eventually separated in June 1997.

In 1998, Paltrow boldly stated, “If two individuals aren’t meant to be together, they simply shouldn’t be,” but fast-forward to 2015, she admitted to Howard Stern that at the age of 22, she lacked maturity. She explained, “I was so young; I had my head stuck in the sand. You can’t make such a decision at 22 years old… He was too good for me, and I wasn’t ready yet.

Additionally, their split left Bruce Paltrow, her father, deeply saddened. In fact, he regarded him as a beloved son. Eventually, she admitted to having developed feelings for him, describing him as incredibly attractive and kind. Essentially, she referred to him as someone akin to Brad Pitt.

Following his split with Paltrow, reports suggest that Pitt momentarily dated his co-star from “Meet Joe Black”. The two were spotted attending the 50th Annual Writers Guild of America Awards together.

It’s told that Aniston and Pitt first met in 1998 through a blind date arranged by their agents. At the time, people weren’t yet using merged names, so they were known as “Hollywood’s golden couple.” They got married in 2000, Pitt made an appearance on Friends in 2001, and in 2002, Aniston expressed her plans for starting a family, saying, “It will definitely happen, but probably not right away.

Unfortunately, on January 8, 2005, the actors made an official announcement that they had parted ways. For those interested, we would like to clarify that our separation is not based on any gossip spread by tabloid media. In a statement, they expressed this point more explicitly. The divorce was finalized in October of the same year, amidst numerous reports circulated by people who closely follow such news.

In the annals of celebrity history, Aniston’s September 2005 interview with Vanity Fair stands out for its candid and emotional exploration of a high-profile breakup.

But years later…they’re friends!

In the year 2004, while working together on the set of “Mr. and Mrs. Smith”, I found myself developing feelings for Brad Pitt, who at that time was still married. It wasn’t until much later that I openly acknowledged this fact after we had both won Oscars.

Encouraged by their children – Maddox, Zahara, Shiloh, Pax, and twins Vivienne and Knox – Brad Pitt and Angelina Jolie tied the knot at their chateau in France in 2014, having been engaged for two years prior.

In 2014, before their surprise wedding, Jolie expressed to Elle that when they come together as two individuals, they inspire, challenge, and complement each other in a way that sometimes drives them a little mad. She explained that after many years of shared history, there’s an extraordinary friendship based on deep comfort, ease, and a profound love, born from having experienced a lot together.

However, Jolie filed for divorce on September 19, 2016, stating irreconcilable differences as the reason. This action initiated an FBI probe into Pitt’s conduct during a flight (he was never charged). Despite certain lulls that gave the impression of peace, the fallout from this event became complicated and remained so.

They finally settled their divorce in late 2024 after an eight-year legal battle.

Following his split with Jolie, Pitt reportedly had connections with several women, ranging from actress Alia Shawkat to jewelry designer Sat Hari Khalsa and architect Neri Oxman.

All filed under “just friends” in the end.

However, Pitt is now involved in a genuine relationship with de Ramon. He was first seen together with the jewelry company executive in November 2022 – two months following de Ramon’s confirmation of separation from husband Paul Wesley, which occurred in the spring. (The actor from “Vampire Diaries” filed for divorce in February 2023.)

Meanwhile, the sightings of Pitt and de Ramon, though sporadic, simply haven’t stopped.

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2025-06-19 17:17