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The Epic Romance of Brad Pitt and Jennifer Aniston: A Journey Through the Years

Although it has been over 15 years since Brad Pitt and Jennifer Aniston ended their relationship, their romance remains one of Hollywood's most captivating tales. From their high-profile wedding to their unexpected reunions, here's a look back at their journey together.

1994: The Casual Encounter Brad Pitt and Jennifer Aniston first crossed paths in 1994 through their managers, who were friends. Aniston recalled in a 2001 Rolling Stone interview, "He was just this sweet guy from Missouri, you know? A normal guy."

1998: A Romantic Spark Their romance didn't ignite until 1998, following Brad's breakup with Gwyneth Paltrow and Jennifer's split from Tate Donovan. Their managers arranged their first date, which Jennifer later described to Diane Sawyer in 2004 as "really fun" and "easy."

September 12, 1999: Red Carpet Debut The couple confirmed their relationship when they walked the red carpet together at the 51st Primetime Emmy Awards.

November 29, 1999: The Engagement At a Sting concert on November 29, 1999, Brad showcased Jennifer's engagement ring, which he had designed with a $500,000 budget and a unique circular diamond setting.

July 29, 2000: The Wedding of the Year Brad and Jennifer's wedding was one of the most talked-about events of 2000. Held on a Malibu bluff overlooking the Pacific Ocean, their ceremony was a lavish affair with 50,000 flowers, a 40-person gospel choir, and a firework display, costing around $1 million.

November 22, 2001: A Friends Appearance In 2001, Brad guest-starred on Jennifer's hit sitcom, Friends. His role was notably antagonistic towards Jennifer's character, Rachel Green.

February 1, 2003: The Love Question During a W Magazine interview in 2003, Jennifer was asked if Brad was the love of her life. She responded thoughtfully, emphasizing their special bond amid the chaos of their lives.

February 2004: Family Plans As Jennifer's time on Friends drew to a close, she expressed her desire to start a family. She believed that working while pregnant was possible and looked forward to slowing down.

May 2004: Rumors Begin Rumors of an affair between Brad and Angelina Jolie, his Mr. & Mrs. Smith co-star, began circulating. Jolie later described their on-set connection as evolving into a deep partnership.

January 7, 2005: The Separation Announcement On January 24, 2005, Brad and Jennifer announced their separation, citing thoughtful consideration rather than tabloid speculation. They emphasized their continued respect and care for each other.

March 25, 2005: Divorce Filing Jennifer filed for divorce from Brad on March 25, 2005.

September 2005: Jennifer Speaks Out In September 2005, Jennifer addressed the divorce, acknowledging her feelings of loneliness and confusion. She criticized the timing of Brad's photos with Jolie, stating it seemed inconsiderate.

October 2, 2005: The Final Divorce Brad and Jennifer's divorce was finalized on October 2, 2005.

September 15, 2011: Brad's Remarks Brad made controversial comments about his marriage to Jennifer in a Parade interview, describing himself as unfulfilled. He later apologized, clarifying that he didn't view Jennifer as dull but rather himself as stagnant.

August 10, 2012: Jennifer's Engagement Jennifer became engaged to actor Justin Theroux, who proposed with a $500,000 ring.

August 23, 2014: Brad and Angelina's Wedding Brad married Angelina Jolie on August 23, 2014, at their French chateau with their six children present.

August 5, 2015: Jennifer's Marriage Jennifer married Justin Theroux on August 5, 2015, almost a year after Brad's wedding.

September 20, 2016: Jolie Files for Divorce Jolie filed for divorce from Brad in September 2016, citing irreconcilable differences.

February 11, 2017: A Text from Brad Brad allegedly texted Jennifer on her 48th birthday, expressing his struggles with his split from Jolie. They reportedly reminisced about their past.

February 15, 2018: Jennifer's Split Jennifer announced her separation from Justin Theroux on February 15, 2018, after two-and-a-half years of marriage.

February 11, 2019: Birthday Party Invitation Brad attended Jennifer's 50th birthday party in February 2019, sparking media speculation about their relationship.

December 14, 2019: Holiday Party Presence Brad was also seen at Jennifer's holiday party in December 2019, arriving early and leaving late.

January 19, 2020: The Viral Moment At the Screen Actors Guild Awards in January 2020, Brad and Jennifer's flirtatious interaction made headlines, fueling rumors of a rekindled romance.

September 17, 2020: Charity Table Read Brad and Jennifer reunited for a charity table read of Fast Times at Ridgemont High in September 2020, displaying playful chemistry during their performances.

June 2021: Jennifer Clears the Air In June 2021, Jennifer clarified on The Howard Stern Show that her relationship with Brad was purely friendly. She expressed her interest in finding a meaningful partnership but not necessarily through online dating.

Brad Pitt and Jennifer Aniston's romance, from its glamorous beginnings to its heartfelt evolution, remains one of Hollywood's most memorable love stories. Despite their separation, their continued connection and friendship highlight the enduring nature of their bond.