2002: While working on Gigli with Jennifer Lopez, Affleck raises eyebrows by placing an ad in the Hollywood Reporter extolling his costar`s "graciousness of spirit, beauty and courage, great empathy, astonishing talent, real poise and true grace." She is still married to her backup dancer Cris Judd. Then, Affleck shows up to help Lopez celebrate the opening of her Pasadena restaurant Madres, giving her a floral arrangement while Judd stood by.
After hanging out together for months (and after Lopez`s divorce). Affleck and Lopez come out as "Bennifer" in her "Jenny from the Block" video. In the video, they kiss, and read tabloid reports about themselves. Affleck also strokes Lopez`s famous posterior. He gives his new love a token of his affection, a yellow-and-white-diamond bracelet.
Affleck presents Lopez with a 6.1-carat pink-diamond solitaire ring custom-made by Harry Winston.
2003: The National Enquirer runs a story about Affleck`s wild night at a Vancouver strip club. It causes trouble for the pair, but Lopez gets over it, telling Affleck, "You`ve had your bachelor party." A month later, Gigli is released, and is critically panned. The L.A. Times says it is "nearly as unwatchable as it is unpronounceable."
Four days before their $2 million wedding, Affleck and Lopez call off the event. "As the [wedding] date got closer, reality set in that this may not be the person Ben wants to spend the rest of his life with," a friend tells PEOPLE.
With his relationship on the rocks, Affleck visits the troops in Iraq. That January, Lopez breaks up with him. "She finally realized they were never going to get married," a close source tells PEOPLE. By June, Lopez marries Marc Anthony.