The Leftovers actor popped the question to Aniston on his 41st birthday on August 10, 2012.
Looking chic in all black and strappy heels, the 47-year-old actress dined at The Smile restaurant with Theroux, 45, who was also dressed in all black.
Though Aniston has not yet commented publicly on the breakup, photogs did catch her flashing a small smile. RELATED: Inside Brad Pitt's Relationship With Son Maddox In the latest on the drama surrounding the Hollywood power couple's relationship, Jolie moved with their six children -- Maddox, 15, Pax, 12, Zahara, 11, Shiloh, 10, and twins Vivienne and Knox, 8 -- into a Malibu mansion.
“My first [thought] was that this was completely easy,” she explained to Pop Sugar of Theroux.
“He is funny, kind and easy to be with."Fast-forward two years and Theroux was ready to make it official.
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The character was widely popular during the airing of the series and was later recognized as one of the 100 greatest female characters in United States television.
Aniston has played the female protagonist in a number of comedies and romantic comedies.
Jen went on to date other hot celebrity guys (including a couple of costars) before finding true love with the adorable Justin Theroux.
While Jen has made headlines for her past relationships, she has also served as an inspiration for women and will forever be one of the shining examples of resiliency after a bad breakup.
Look back at the famous men who have been "more than friends" with the beloved actress.