- Special Features
- Blogs & Columns
- Fun & Games
With Jennifer Aniston’s recent announcement of her engagement to actor Justin Theroux comes the many memories of past Aniston relationships. The beautiful actress has been rumored to have dated numerous Hollywood men in her past. While hoping that Aniston has finally found her happily ever after, here’s a look back at Aniston’s top ten rumored hook-ups and relationships.
10. Jennifer Aniston dated Charlie Schlatter in the early 1990s. While the two played brother and sister on the sitcom Ferris Bueller, off screen they had a brief romantic encounter.
9. After Charlie Schlatter, it was reported that Aniston dated Adam Duritz in 1995. This relationship was short-lived when Duritz hooked up with Aniston’s friend and co-star Courteney Cox. Cox and Duritz then ended up dating for several years.
8. Aniston later had a three-year relationship with Tate Donovan. Donovan and Aniston were engaged and split up in 1998.
7. Aniston’s most famous relationship was her marriage to Brad Pitt. The two began dating in 1998 and married in Malibu in 2000. While Hollywood believed that this pair was a rare successful marriage, the two then split suddenly in 2005.
6. After her divorce with Pitt for "irreconcilable differences," Aniston dated Vince Vaughn in 2005. While filming The Break Up together, the pair was rumored to be dating and then announced their relationship later in the year. This romance was short-lived as they broke up later in 2006.
5. Aniston was then rumored to have been dating Paul Sculfor for a few short months in 2007. The two were spotted out in public for romantic dinners, and soon after that were no longer seen together.
4. John Mayer was then next on the list of Aniston’s hook-ups. From 2008 to 2009, the two tried to make their relationship work. Their relationship was on-again, off-again for the majority of their year together, and eventually ended for good in 2009.
3. Aniston and Bradley Cooper were rumored to have a short-lived relationship in June of 2009. The two went on a date at a romantic restaurant called Il Cantinori in Manhattan. Their one romantic date seemed to be the end of their relations with each other.
2. In 2010 Aniston and Gerard Butler had a secret relationship with one another while filming The Bounty Hunter. Their relationship is still secretive as neither one of them ever confirmed that they even went on a date with each other, but they were spotted together in public often.
1. Aniston has found her happy ever after with actor Justin Theroux. The two quietly dated in 2011 and have now announced their engagement. This will be Aniston’s second marriage and Theroux’s first.