Lopez and Affleck first met in 2001 while filming their 2003 rom-com Gigli. Although the Hustlers actress was married to her husband Cris Judd at the time, Affleck later admitted her marriage allowed them to get to know each other and form a close friendship without "any of the falseness that goes with a courtship."
The power couple began dating not long after the "On the Floor" singer filed for divorce and got engaged that same year, but it would be their popularity and constant public attention that later spelled doom for their relationship.
"We began to feel that the spirit of what should have been the happiest day of our lives could be compromised," they explained in a joint statement after canceling their 2003 nuptials. "We felt what should have been a joyful and sacred day could be spoiled for us, our families and our friends."
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Both Lopez and Affleck quickly moved on to new marriages. The pop star tied the knot with Marc Anthony in 2004, while the Gone Girl star and Jennifer Garner said "I do" the following year after costarring together in Elektra.
Although the former flames remained friendly, they sparked dating rumors nearly two decades later when they reconnected in Los Angeles in April 2021. Throughout the year, their whirlwind romance continued and the duo was spotted cuddling and kissing all over the country from flashy Miami getaways to romantic walks in Montana.
A year after they sparked rumors of romance, Affleck got down on one knee and popped the question — for the second time! — with a gorgeous, green diamond ring while the "Lets Get Loud" singer was lounging in a bubble bath.
"I was taken totally off guard and just looked in his eyes smiling and crying at the same time trying hard to get my head around the fact that after 20 years this was happening all over again," she explained in an April edition of her newsletter. "I was quite literally speechless and he said, ‘is that a yes?’ I said YES of course that’s a YES."