.Jenny Shimizu marked Angelina Jolie's inaugural public relationship with a woman, and Jolie was deeply enamored with her. They crossed paths during the filming of Foxfire, and although the exact timeline is somewhat uncertain, their connection endured on-and-off from 1996 to 2000.number 2 .Less prominently discussed than her other relationships, Angelina reportedly dated her Playing God (1997) co-star Timothy Hutton in 1996, shortly following her separation from Jonny Lee Miller. The duration of their relationship remains unclear, but it appears to have overlapped when, in 1999, she encounterednumber 3 Rumors surfaced of a brief liaison between Angelina and Irish heartthrob Colin Farrell during the shooting of Alexander in 2003. Despite sparking curiosity among fans and media, neither party confirmed the alleged romance.number 4 .Miller and Jolie crossed paths while collaborating on the 1995 film Hackers. They subsequently exchanged vows in a small civil ceremony in 1996. However, their union faltered just a year later, citing hectic schedules as the primary cause. Jolie initiated divorce proceedings in 1999, which were finalized the same yearnumber 5 .Jolie sent shockwaves in 2000 by marrying Billy Bob Thornton. Despite their passionate connection, the marriage proved short-lived, ending abruptly in 2002 and culminating in a finalized divorce the following yearnumber 6 .Val Kilmer and Angelina didn't pursue a romantic relationship until after their film's release in 2004. Kilmer expressed gratitude for being "rescued" by his former co-star in a touching tributenumber 7 .Angelina Jolie's rumored relationship with The Weeknd was reportedly met with disapproval from her children, who wished for her reconciliation with her former husband, Jonny Lee Miller. Jolie's love life continues to captivate Hollywoodnumber 8 . Speculations swirled about Angelina dating actor and musician Jared Leto twice: first in 2004 and later in 2010. However, these alleged relationships remained brief and unconfirmednumber 9 . On August 23, 2014, Brad Pitt and Angelina Jolie exchanged vows in an intimate destination wedding. Surrounded by 20 close friends and relatives, including their six children, the couple, who began their relationship in 2004, solidified their bond. Their subsequent split involved disputes over their children and a French winery.