Jennifer Aniston: The Beginning

His age: 35-42

Duration: 1998-2005

Brad Pitt’s romantic journey with Jennifer Aniston began in 1998 when they first crossed paths. Their relationship quickly blossomed, leading Pitt to propose to the Friends star in 1999.

The couple exchanged vows in a lavish ceremony on July 29, 2000, in Malibu, surrounded by around 200 guests, an abundance of flowers, multiple musical acts, a gospel choir, and a grand fireworks display. The wedding was a spectacle to behold, with Jennifer’s father, John Aniston, describing his daughter as “beautiful” on her special day.