Here’s How Jennifer Anniston and Brad Pitt’s Agents Set Them up on Their First Date

In the late '90s, Hollywood witnessed the union of two of its brightest stars—Brad Pitt and Jennifer Aniston. Not many know that their union was possible because of their agents, who introduced them to each other in 1998. The pair met each other for the first time at a dinner party that was not exactly accidental for the couple. The agents of both actors ensured they were introduced to each other at the party, which became a stepping stone for their relationship in the future. 

Soon the power couple's romance blossomed against the backdrop of their soaring careers. Pitt, acclaimed for roles in Fight Club and Seven, and Aniston, charming audiences as the affable Rachel Green on Friends, kept their relationship hush-hush initially, making their public debut at the 1999 Emmy Awards.

On July 29, 2000, the duo exchanged vows in a lavish ceremony in Malibu, California, and set out together for a happy married life. The guests included friends, family, and co-stars. In her vows, Aniston charmingly pledged always to make Pitt's "favorite banana milkshake." However, despite the fairytale beginning, their marriage encountered stormy weather. The couple officially called it quits in 2005, paving the way for Pitt's subsequent marriage to Angelina Jolie and Aniston's union with actor Justin Theroux.

Aniston and Pitt made an effort to dispel rumors that Pitt had an affair with Angelina Jolie while filming Mr. & Mrs. Smith. They stated then, "For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media." Pitt seemed to disparage Aniston, his wife from 2000 to 2005, in a 2011 interview with Parade magazine. He said back then, "I spent the ‘90s trying to hide out, trying to duck the full celebrity cacophony. I started to get sick of myself sitting on a couch, holding a joint, hiding out. It started feeling pathetic. It became very clear to me that I was intent on trying to find a movie about an interesting life, but I wasn’t living an interesting life myself. I think that my marriage [to Aniston] had something to do with it. Trying to pretend the marriage was something that it wasn’t."

Brad had to backtrack and clarify his earlier comments, which were an indirect jab at Jen, which insinuated she was the boring one. He went so far as to issue a statement for clarity's sake. Post their tragic separation, Aniston shared, "I really do hope that someday we can be friends again. I will love [Brad] for the rest of my life. He's a fantastic man. I don't regret any of it, and I'm not going to beat myself up about it," in an interview with Vanity Fair.