#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.

By Isabel Jones
Updated May 11, 2021 @ 6:00 am
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Who: Legendary multi-hyphenate Jennifer Lopez, 51, and Oscar-winning actor-cum-director Ben Affleck, 48.

Arrest Warrant Issued For Ben Affleck After Alleged Threats
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How they met: Ben and Jen reportedly met in 2001, on the set of their notoriously low-brow film Gigli. At the time, J.Lo was still married to her second husband, dancer Cris Judd, but they divorced in 2002 and she and Affleck began dating soon after. They got engaged later that same year - Affleck proposed while playing Lopez's song, "I'm Glad."

Lopez told Diane Sawyer that her relationship with Affleck was "bigger and realer" than those she'd had previously.

Gigli California Premiere
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Why we loved them: As Jen herself will admit, her and Affleck's romance was one of the first of the major celebrity gossip era, or the "birth of the tabloids" as Lopez calls it. The frenzy surrounding their relationship even bore its own (and one of the first) celebrity portmanteaus: Bennifer.

Though the lightning-quick engagement is something of a craze among young Hollywood today, Bennifer essentially started the trend in 2002. Ben proposed with one of the most iconic rings of the 21st century: the 6.1-carat Harry Winston pink diamond (which is appraised at around $1.2 million).

'Gigli' Press Conference with Jennifer Lopez, Ben Affleck and Justin Bartha
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Plus, we have no choice but to stan a couple who shares fashion tips.

In 2014, Lopez told Andy Cohen that she subtly guided his early aughts style transformation. "I did kind of like say, 'You need to be, you know, you're a movie star! You should wear a suit, you know? You should do this with your hair," she said. "He had some good fashion moments when he was with me."

When they peaked: There is absolutely question about it. From 1:35 and on in the music video for "Jenny from the Block" is definitively when they peaked as a couple.

The breakup: The wedding of the century was initially scheduled for September 2003, but it was "postponed" just one week prior, reportedly due to the "excessive media attention." In early 2004, "postpone" evolved into "called off" as it was announced that J. Lo had "ended her engagement to Ben Affleck."

Rumors abound as to why Bennifer ultimately sang their swan song. Gigli's release and box office flop couldn't have done the couple any favors. Lopez describes the fallout as leaving her "eviscerated." She told Vanity Fair, "I lost my sense of self, questioned if I belonged in this business, thought maybe I did suck at everything."

Gigli California Premiere
Credit: Jeff Kravitz/Getty Images

For Affleck, it took years to reestablish himself as a major player in Hollywood post-Gigli. It wasn't until his Academy Award win for Argo that he really returned to the cinematic fore.

The New York Post claimed that Ben "wasn't ready to settle down" and straight-edge Jen was fed up with his partying and "wandering eye."

Of course, the media was hardly blameless in the rise and fall of Bennifer. In their joint statement announcing they'd postponed their wedding, Ben and Jen wrote, "When we found ourselves seriously contemplating hiring three separate 'decoy brides' at three different locations, we realized that something was awry." Just your average something borrowed, something blue, someone paid to impersonate you …

Where they are now:

Since their high-profile split in 2004, Ben and Jen have both remarried and divorced.

Affleck wed another famous Jennifer (Garner) in 2005, igniting the era of Bennifer 2.0. The pair were married for 10 years and had three children together (Violet, 15, Seraphina, 12, and Samuel, 9) before announcing their separation in 2015.

85th Annual Academy Awards - Arrivals
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Post-Garner, Ben moved on to SNL producer Lindsay Shookus - after their split in summer 2018 he started dated 22-year-old Playboy model Shauna Sexton. He was most recently linked to Ana de Armas before splitting up with her in 2020.

Lopez wed fellow singer Marc Anthony in 2004. They began dating soon after her "first big heartbreak" with Ben. Of the courtship, Lopez told Today "The first person who shows up and gives me a little comfort and gives me a little chemistry, boom, we're in. To have one of my best friends, who I'd known for years, who I actually love and did have chemistry with, come into my life and say, 'I'm here.' ... What you need to know is, nobody can save you or heal you. Only you can do that for you."

Lopez and Anthony welcomed twins (Max, 13, Emme, 13) in 2008, and like Affleck and Garner, divorced after 10 years of marriage in 2014.

20th Annual Childrens Fund Gala - Arrivals
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Lopez was most recently engaged to Alex Rodriguez. The pair started dating in 2017, but in April 2021, announced that they were going their separate ways. "We will continue to work together and support each other on our shared businesses and projects," they said in a joint statement. "We wish the best for each other and one another's children. Out of respect for them, the only other comment we have is to say is thank you to everyone who has sent kind words and support."

2018 MTV Video Music Awards - Arrivals
Credit: Jamie McCarthy/Getty Images

If you read all the way to here you probably know what comes next in this story. Following her split with A-Rod, Lopez and Affleck were spotted hanging out again. Reports are still swirling about a potential rekindled romance (even Matt Damon wants to see it happen) but as of May 11, 2021, neither has confirmed nor denied.

This story was updated.