Cancelled Engagements To Rekindled Relationships! Jennifer Lopez & Ben Affleck's Relationship Timeline

It's no secret that Ben Affleck and Jennifer Lopez are one of Hollywood's hottest couples of 2021, but their relationship has seen its fair share of ups and downs.

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2002 was a big year for Bennifer! Affleck famously appeared in Lopez's "Jenny from the Block" music video, and the happy couple also filmed their second movie together — Jersey Girl directed by Kevin Smith.

Following a whirlwind summer relationship, in November, the pair announced their engagement.

"...he is brilliantly smart, loving, charming, affectionate," Lopez gushed to Diane Sawyer in the bombshell interview. "And I just admire him in every way. I respect him. I feel like he teaches me things."

Calling it quits! Public attention took a toll in 2003, leading the duo to postpone their impending nuptials only days before the wedding was meant to take place.

"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. "We felt what should have been a joyful and sacred day could be spoiled for us, our families and our friends."

Only four months later, the couple officially ended their relationship, which J.Lo describes as her "first big heartbreak".

Moving on! Following their January split, the Hustlers actress didn't take long before she jumped head first into a brand new relationship — and planned a new wedding! Lopez married "When I Dream at Night" singer Marc Anthony in June of 2004.

Affleck wasn't far behind. After costarring alongside Jennifer Garner in Elektra the year before, the high profile pair began dating, and tied the knot in 2005.

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Fast forward! 17 years after their bombshell breakup, The Town star and the "Let's Get Loud" artist set tongues wagging when they were spotted together in Los Angeles shortly after the pop star's split with slugger Alex Rodriguez.

Once the sightings started, they didn't stop! The A-Listers were caught spending a few nights in Montana at the ultra-exclusive Yellowstone Club where they reportedly swam, took romantic walks and lounged together in the hot tub.

Days later, the couple went "PDA official" when they were seen sharing "a kiss in between sets" at Anatomy Fitness in Miami.

Instagram official! After months of speculation, J.Lo was finally ready to show off her man to the world! The megastar took to social media to post a series of birthday pics, including one of her and the Gone Girl actor locking lips in a steamy kiss.

Over the next few days, the Internet was teeming with nonstop sultry snapshots of the A-List lovebirds as they sailed the French Riviera.

Later that summer, it looked like Mr. Affleck might be considering popping that big question to his leading lady when he was spotted browsing engagement rings at Tiffany's in Century City, Calif., accompanied by his mother and his son.

This came only two months after a source spilled the pair may make it official sooner rather than later. “Let’s be honest, the new relationship might technically only be a few weeks old, but in reality they are picking up where they left off. Jen and Ben both know everything about each other — the good, the bad and the ugly. They are not starting at square one.”

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Bennifer 2.0 have been far from shy about flaunting their love, but they set the red carpet ablaze when they made their first red carpet debut as a couple since their initial split.

The head-over-heels duo attended the Venice Film Festival together on Friday, September 10 to support Affleck’s starring role in The Last Duel.

In it for the long haul! In early November, a source dished that despite being apart to film different projects, the high profile pair are "looking forward to their future together."

"They are madly in love," the insider revealed. "Spending time in different cities during the week has made them miss each other like crazy and fall even more in love."

Family first! OK! learned in mid-November that J.Lo, Affleck, and Garner planned to spend Christmas together with their kids as a blended family. The "Love Don't Cost A Thing" singer shares 13-year-old twins, Maximilian and Emme, with Anthony, while the Justice League star shares Violet, 15, Seraphina, 12, and Samuel, 9, with the 13 Going on 30 actress.

“Once it was clear that Ben and Lopez were serious about getting back together, Jennifer reached out," an insider told Radar. "When you have children with an ex and that person starts dating again, all three of you are linked together like it or not. Jennifer was determined to make sure that she had a relationship with J. Lo, if for nothing else, so that things were not awkward for her kids."

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During her appearance on the Today show on Thursday, November 17, while promoting her new rom-com, J.Lo admitted she wouldn't mind getting married again.

“The two words ‘Marry Me’ — are those two words you would like to hear in the future?” Hoda Kotb teased, to which the 52-year-old replied, “I don’t know. Yeah, I guess ... I mean, you know me. I’m a romantic. I always have been.”

In early December, the cuddly couple packed on the PDA once again — this time, they were courtside at a basketball game while cheering on Affleck's favorite team the Boston Celtics.

The 49-year-old actor faced backlash after speaking perhaps a little too candidly in an interview with Howard Stern on December 14 in which he seemed to claim he "would probably still be drinking" if he hadn't divorced the mother of his children.

The Triple Frontier star later clarified on The Jimmy Kimmel Show that his quotes were severely taken out of context, and the media twisting his words "hurt his feelings."

"I had gone on and said how much we respect each other and cared about each other and cared about our kids and put them first," he explained, adding the coverage of the interview "made me out to be the worst, most insensitive, stupid awful guy."

Following reports that claimed the Grammy winner was "livid" with her boyfriend over his controversial interview, Lopez was quick to shut down the rumor mill.

"This story is simply not true. It is not how I feel," Lopez told People. "I couldn't have more respect for Ben as a father, a co-parent, and a person."