Jennifer Aniston's Love Life, Lost First Love, Brad Pitt-Angelina Jolie Drama To Dating A Hypnotist

Jennifer Aniston has never been one to shy away from speaking her truth like 'Rachel Green,' especially when it comes to matters of the heart. In a new candid interview with Vanity Fair, the 56-year-old actress reflected on the time two decades ago when her marriage to Brad Pitt ended when rumours of his growing closeness with his Mr. And Mrs. Smith's co-star Angelina Jolie made headlines.

"It was such juicy reading for people," she said. "If they didn't have their soap operas, they had their tabloids." While she admits she took it personally at the time, her approach was simple to gather herself and keep walking. Although Jennifer has moved on in her personal life, her recent comment made fans recall her dating life, which became a staple for readers. Let's take a look at it. 

Jennifer Aniston's early relationships in the 90s

Jennifer Aniston rose to fame in the 90s after playing 'Rachel Green' on the sitcom, Friends. Simultaneously, she was trying to find the love of her life in that decade. After becoming a household name, she dated actor, Charlie Schlatter briefly in 1990 after meeting on the set of Ferris Bueller. When things didn't worked out, she found her first love in Daniel McDonald at 25, who later died in 2007 from Brain Cancer. Recalling their bond, Jennifer once said to The New York Times:

"He was my first love — five years we were together. He would have been the one. But I was 25, and I was stupid. He must have sent me Justin [second ex-husband] to make up for it all"

In the mid-90s, Jennifer was also linked to musician, Adam Duritz, frontman of Counting Crows. But the relationship was short-lived. Around the same time, she also dated actor, Tate Donovan, who later appeared on Friends as her on-screen love interest. However, they parted ways after being together for three years before ending in 1998.

Jennifer Aniston and Brad Pitt's drama 

Jennifer Aniston began a high-profile romance with Brad Pitt in 1998. At the peak of her career, Jennifer married him in July 2000 in a lavish Malibu ceremony. They were addressed as Hollywood's 'golden couple' for years. However, in early 2005, the pair announced their separation, finalising their divorce later that year. Media speculation tied their split to Pitt's growing closeness with Angelina Jolie. Although Jennifer maintained silence, the 'love-triangle' drew in readers. Next, Brad went ahead to date and marry Angelina, and they have six kids, but they parted ways after 2016 in a messy divorce. 

Jennifer Aniston's alleged romances to failed second marriage 

After her divorce, the Friends actress was linked to several actors, including her The Break-Up co-star, Vince Vaughn. Their relationship lasted about a year before they split in 2006. She was later rumoured to have dated British model, Paul Sculfor in 2007. A year later, she again began dating John Mayer, which ended after months. Jennifer gave a second chance at love and married her Wanderlust co-star, Justin Theroux, in August 2015 at their Bel Air home. But they mutually parted ways in February 2018. Their divorce statement read:

"This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our friendship. Normally, we would do this privately, but given that the gossip industry cannot resist an opportunity to speculate and invent, we wanted to convey the truth directly."

Since her split from Theroux, Jennifer has kept her dating life mostly private. She is currently dating Jim Curtis, a transformational coach and hypnotherapist. They were first spotted together in late June 2025, and their relationship was confirmed after they were seen on a yacht with friends in Mallorca. However, not much is known about their bond.

Despite her efforts to keep things private, Jennifer Aniston's love life always found attention. It came under intense media scrutiny, Yet, the actress has always focused on love and happiness over everything else. 

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