As Lopez and Ben Affleck are appearing out and about together more often recently and heating up the headlines, let's take a look back the duo's history.
December 2001
Lopez and Affleck met on the set of the rom-com "Gigli," where they played criminals stuck on a job together and the pair strike up real-life friendship.
April 2002
Speculation that Ben and Jen may be more than just friends began after he took out a full page ad in trade publications to both promote their film and praise her performance.
"It has been nothing but an honor and a pleasure to work with you," the ad read. "I only wish I were lucky enough to be in all your movies." Signed: "With love, respect, and gratitude, Ben Affleck."
Lopez and Chris Judd file for divorce during the summer of 2002, but have reportedly been split for a bit by then.
"Jennifer Lopez and Cris Judd have announced they have resolved all issues arising out of their marriage," the couple's lawyers say a statement at the time. "The resolution was extremely amicable . . . The two will remain friends."
August 2002
Paparazzi photos began circulating of Lopez and Affleck smooching.
November 2002
The couple get engaged after Affleck pops the question with a magnificent, custom 6.1-carat pink diamond ring from Harry Winston.
He also appears as Lopez's love interest in the music video for her single "Jenny From the Block," the storyline of which takes on the paparazzi treatment of their relationship.
In the video, Affleck -- literally -- kisses her famous booty in a scene of the couple on a yacht.
March 2003
Lopez and Affleck make a stunning pair on the red carpet at the 75th Annual Academy Awards.
The couple attend the premiere of their "Gigli" film, which eventually bombs at the box office.
September 2003
Days before the pair are set to wed, they postpone their nuptials and release the following statement:
"Due to the excessive media attention surrounding our wedding, we have decided to postpone the date. When we found ourselves seriously contemplating hiring three separate 'decoy brides' at three different locations, we realized that something was awry. We began to feel that the spirit of what should have been the happiest day of our lives could be compromised. We felt what should have been a joyful and sacred day could be spoiled for us, our families and our friends."
Sources told CNN at the time that the couple was "taking a break."
January 2004
The duo officially called off their engagement and split.
March 2004
Another film in which the two costarred together, "Jersey Girl," is released and underwhelms at the box office.
Lopez married friend, singer Marc Anthony, with whom she shares twins -- a son and a daughter.
In her 2014 book, "True Love," Lopez reportedly wrote that the end of her relationship with Affleck was her first "real heartbreak" and "Marc came back into my life three days after I should have been at the altar saying 'I do' to another man."
A year later, Affleck married actress Jennifer Garner in a private ceremony. They go on to have three children together.
Fans are stunned when Lopez and Anthony announce they are separating. He filed for divorce in April 2012.
There's even more shock when Garner and Affleck announce their split. Their official divorce filing came two years later.
"They remain friends and continue to co-parent their three kids amicably," a source close to the couple told CNN at the time. "They had always planned to divorce but just needed time. As always, their children are their first priority."
March 2019
Lopez and former baseball player Alex Rodriguez become engaged, two years after they started dating and 20 years after she autographed a poster for the self-avowed Lopez fan.
February 2020
He said he has no regrets about making "Gigli" because "I made a great friendship with Jennifer Lopez, who I think is a fabulous person and I'm so excited for her continued success."
"I don't think she always got the respect that she deserved, in part, because she was a powerful woman," he said. "And also because she was a Latina and she was really groundbreaking and nobody wanted to acknowledge that. They just wanted to kind of hate, so it's nice to see her having that success."
March 2021
Some confusion as Lopez and Rodriguez reportedly split, only to say days later in a statement that they were still a couple after all.
April 2021
Rodriguez and Lopez formally announced their engagement was called off.
They released the following statement.
"We have realized we are better as friends and look forward to remaining so. We will continue to work together and support each other on our shared businesses and projects. We wish the best for each other and one another's children. Out of respect for them, the only other comment we have to say is thank you to everyone who has sent kind words and support."
Soon after, Affleck was photographed visiting Lopez's Los Angeles home.
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