Lopez had another high-profile coupling in 2002 when she began dating Ben Affleck. The relationship left a big mark on her career. Lopez dedicated to him most of her third studio album, This Is Me...Then, and featured him in the voyeuristic lead video, "Jenny From the Block." The pair also starred together in the 2003 film Gigli — an epic commercial and critical flop. After numerous canceled weddings, the pair split in 2004.
(Photo: Columbia Pictures)