With looks that could launch a thousand ships and a dating history that can make even gods go green with envy, Hollywood heartthrob Brad Pitt’s journey through romance is nothing short of a blockbuster with an ensemble cast that boasts of glamazons in the form of ex-girlfriends and spouses.

As the Oscar-winning actor navigated the glamorous landscape of Hollywood, he left a trail of starry exes in his wake. From former wives Angelina Jolie and Jennifer Aniston to past loves like Gwyneth Paltrow, Christina Applegate and more, Pitt’s romantic escapades are for the books.

However, after a relatively low-key period post-divorce from Jolie, Pitt seems to have stepped back into the limelight hand-in-hand with his current girlfriend, jewellery designer Ines de Ramon.

Yep, despite the occasional spotlight on past flames, it’s the fresh whispers of Pitt and de Ramon doing the rounds in Hollywood that have tongues wagging. This brings us to…

Deconstructing Brad Pitt’s dating history and list of girlfriends 

In light of recent events, we decided to delve deep into the star-studded romantic past, present and possible future of the man who has charmed his way through Hollywood for over four decades.

Sinitta Malone (1986-1988)

Picture Credits: Twitter/Sinitta Malone

The first name on Brad Pitt’s list of girlfriends is British pop sensation Sinitta. In a dazzling revelation during I’m a Celebrity… Get Me Out Of Here! in 2011, the pop star gave details about her alleged romance with Pitt from 1986 to 1988. Describing Pitt as “beautiful with the most amazing body,” Sinitta reminisced about their fun and sweet two-year escapade.

The disclosure added an enigmatic touch to Pitt’s journey in the entertainment industry, offering a glimpse into a lesser-known romantic chapter from his past.

Robin Givens (1988-1989)

Picture Credits: Instagram/Robin Givens

Pitt was linked to Head of the Class star Robin Givens back in the 80s when she was already married to Mike Tyson.

Tyson wrote about his ex-wife’s alleged affair in his memoir Undisputed Truth, mentioning finding them in a car together. Givens later rubbished his claims by saying, “We were coming home from, like, a screening or something.” She also vehemently denied Tyson’s assertion of catching them in bed on a talk show, saying, “Never, ever, ever happened.”

Jill Schoelen (1989)

Picture Credits: Twitter/Jill Schoelen

Pitt’s infatuation with former American actor Jill Schoelen forged on the set of Cutting Glass. However, their romance took a surprising turn when Schoelen fell in love with the film’s director, leading to their much-written-about breakup in 1989.

Schoelen, in 2013, described Pitt as a “deep and soulful” man who showered her with beautiful poems during their time together.

Christina Applegate (1989)

Picture Credits: Twitter/Christina Applegate

Applegate and Pitt’s fleeting romance began in 1989 when they both attended the MTV Movie Awards together. However, their connection didn’t extend beyond that night as the Bad Moms actor soon left him for another guy.

Recalling her teenage encounters with Pitt and 90210 star Jason Priestley (Pitt’s former roommate), Christina Applegate recounted moments of cosiness over barbecue nights on the sets of Married … With Children. 

Elizabeth “E.G.” Daily (1989-1990)

Brad Pitt had a brief fling with actor-singer E.G. Daily. In a revealing moment on E!’s True Hollywood Story in 2021, Daily shared details of her short-lived romance with Pitt, highlighting his intense dedication to his work and a visceral drive toward something significant.

Juliette Lewis (1989-1993)

Picture Credits: Instagram/Juliette Lewis

The next name in Brad Pitt’s dating history is his Too Young to Die? co-star Juliette Lewis. The two met when Pitt was 27 and Lewis was just 17 (!) and dated from 1989 to 1993. Lewis expressed their deep, non-boring love in interviews, and Pitt later praised their relationship as one of his “greatest” in a 1995 Vanity Fair interview.

Jitka Pohlodek (1994)

Attending the premiere of Legends of the Fall in 1994, Pitt brought model Jitka Pohlodek as his date. While they never publicly spoke about their brief romance, Pohlodek once gushed in an interview that Pitt “glows”, hinting at their brief fling in the early 90s.

Gwyneth Paltrow (1995-1997)

Picture Credits: Instagram/Gwyneth Paltrow

Next up on the list of Brad Pitt’s girlfriends is Goopreneur Gwyneth Paltrow. Paltrow wasn’t just another woman in Pitt’s life, the two were pretty seriously committed, so much so that they even got engaged.

They first met on the set of Se7en in 1995 and later got engaged in 1996, only to call off the engagement in 1997. Paltrow detailed the “fantastic” proposal during a 2023 Call Her Daddy episode, highlighting that they continue to be friends.

Jennifer Aniston (1998-2005)

Picture Credits: Instagram/Jennifer Aniston

The next A-lister in Brad Pitt’s dating history is Jennifer Aniston.

Their relationship began in 1998 and their love was all fireworks, so much so that they soon tied the knot in a grand Malibu wedding on July 29, 2000, with 200 guests and 50,000 flowers in attendance.

The two were together for five years but in a surprising turn of events in January 2005, Pitt and Aniston announced their separation, emphasising it wasn’t fueled by tabloid speculation. Aniston filed for divorce in March 2005, finalized by October, marking the end of their seven-year strong union.

“We would like to announce that after seven years together we have decided to formally separate. 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,” the pair had said in a joint statement to People magazine.

Pit then publicly moved on to Angelina Jolie and the Friends star got married to Justin Theroux. However, staying true to their statement, the two have tried to stay friends over the years. Pitt and Aniston occasionally texted each other and he even famously attended her 50th birthday in 2019. Despite memorable encounters, insiders clarified in 2020 that a romantic reconciliation wasn’t on the horizon.

In 2021, Aniston further affirmed their friendship, stating in an interview with Howard Stern that she and Pitt are “buddies” and “friends”, highlighting their evolution from a spectacular wedding to a mature and endearing connection.

Angelina Jolie (2003-2016)

Picture Credits: IMDb/Mr. & Mrs. Smith

Angelina Jolie and Brad Pitt’s love story began on the set of Mr. & Mrs. Smith in 2003, while the Hollywood heartthrob was still married to Aniston. Jolie recalled their initial friendship in an interview with Vogue in 2007, saying, “We found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair.”

After Pitt and Aniston’s separation in 2005, Brangelina became a thing and started making public appearances together. The next year in the summer of 2006, Jolie, who was already a mother to son Maddox Chivan, adopted daughter Zahara Marley, emphasising the idea of creating a family together. Pitt also decided to officially adopt these two remarkable young individuals as his own.

In 2006, Pitt and Jolie welcomed their first biological child Shiloh Nouvel and later adopted Pax Thien from Vietnam. Their family expanded further with the birth of twins, Knox Léon and Vivienne Marcheline, in 2008. The couple married much later in 2014 in a simple and relaxed wedding at their Château Miraval estate chapel, a laughter-filled day shared with their children.

However, their married life blessed with six children took a turn for the worse in 2016 when Jolie filed for divorce, citing Pitt’s abusive behaviour as the primary reason. Pitt expressed sadness in a public statement and denied allegations of abuse. He said, “I am very saddened by this, but what matters most now is the well-being of our kids. I kindly ask the press to give them the space they deserve during this challenging time.”

Despite being declared legally single in 2019, the custody and asset negotiations continue, marking the ongoing complexities of their post-marriage relationship.

Sienna Miller (2017)

Picture Credits: Instagram/Sienna Miller

Dating rumours between Brad Pitt and Sienna Miller surfaced in April 2017, triggered by their engrossing conversation at a Lost City of Z dinner event in LA. An insider revealed to Us Weekly that the two were “spending some time together,” fueling speculation about a potential romance. Two months later, the duo reunited at England’s Glastonbury Festival alongside Bradley Cooper, adding more fuel to the fire.

Despite shared events and meetups, neither Pitt nor Miller publicly addressed or confirmed the nature of their relationship, leaving fans still wondering if they ever dated.

Neri Oxman (2018)

Following his separation from Jolie, Brad Pitt’s romantic life made headlines when he spent time with professor and architect Neri Oxman in April 2018. A source revealed to People magazine that “It took him a long time to date, but he is now,” pointing to George and Amal Clooney’s relationship as the inspiration for Pitt to move on. The source further highlighted Pitt’s appreciation for women who challenge him intellectually, a quality he admired in Amal.

However, in October of the same year, Oxman denied any romantic involvement with Pitt. Despite dismissing the dating rumours, she praised him as “the last of the Mohicans in post-Netflix Hollywood”, acknowledging his unique ability to blend the timely and timeless aspects of cinema. While their connection may not have been romantic, the episode provided a glimpse into Pitt’s post-divorce journey and his pursuit of meaningful connections.

Nicole Poturalski (2019-2020)

In the summer of 2020, Brad Pitt’s romantic escapades led him to a short-lived romance with German model Nicole Poturalski. The duo’s connection, however, had roots extending back at least a year, with witnesses recalling a flirtatious interaction at a Berlin Film Festival party in 2019.

Their paths converged again in August 2020 when they were spotted enjoying each other’s company at Château Miraval. In the same month, public confirmation of Pitt’s relationship with the then-27-year-old model occurred when they were seen arriving at Le Bourget airport outside Paris. Their romance, however, concluded after two months, described as a “short-lived relationship that was never too serious,” as confirmed by US Weekly.

Emily Ratajkowski (2022)

Picture Credits: Instagram/Emily Ratajkowski

After a hiatus of about two years, Pitt once again found himself in “love”, this time with model Emily Ratajkowski. Following a split from her estranged husband Sebastian Bear-McClard, Emily started dating Brad in September 2022. People magazine reported that the two were “spending a lot of time together,” although the nature of their connection remained uncertain.

There were reports that Ratajkowski was not seeking a serious romance post-divorce. However, she was dubbed perfect for Pitt by many news portals. Described as having the vibes that Pitt appreciates, Ratajkowski, an art enthusiast like the Oscar winner, engaged in enjoyable conversations with him. While an attraction was acknowledged, their interaction was later clarified as not developing into anything serious.

Ines de Ramon (2022-2023)

Making their public debut at a Bono concert in Los Angeles in November 2022, Brad Pitt and Ines de Ramon’s relationship gained attention about two months after de Ramon’s separation from husband Paul Wesley. Sources close to de Ramon confirmed that they had been dating for a few months, having initially met through a mutual friend.

While not described as an exclusive relationship, Pitt was reportedly “really into” de Ramon. In December 2022, they attended the L.A. premiere of Pitt’s film Babylon together, with photographs capturing their flirtatious and happy demeanour at the afterparty. Celebrating Pitt’s 59th birthday at an Italian restaurant in Hollywood, sources noted the couple’s evident happiness, dubbing the two as being “in love”.

Cut fall 2023 and the two have become a bonafide thing with a stable and steady future

Frequently Asked Questions (FAQs)

– Who is Brad Pitt dating currently?
Brad Pitt is currently dating jewellery designer Ines de Ramon. They made their first public appearance in November 2022.

– How long were Brad Pitt and Jennifer Aniston married?
Brad Pitt and Jennifer Aniston were married for five years, from 2000 to 2005.