Bennifer’s Twisted Journey To True Love

February 27, 2023 | Sammy Tran

Bennifer’s Twisted Journey To True Love

The epic romance that is Bennifer started 20 years ago. Now, they're back together—and it's blown everyone's minds. But even as we bask in the glow of this couple's second chance at happiness, we mustn't forget how it all began. Their road to true love has been anything but smooth-sailing. And for all us gossip fiends, this story is chockful of drama, heartbreak, and scandalous rumors.

1. They Made A Terrible Film Together

Let's take it all the way back to 2002. Our two stars met on the set of the doomed rom-com, Gigli. Although Ben Affleck and Jennifer Lopez sizzled on screen, not even their chemistry could save this film from becoming an undeniable flop. Professionally, Gigli really took Affleck down a notch—but romantically, it set him up for one of the wildest rides of his life.

He later said, "And I did get to meet Jennifer, the relationship with whom has been really meaningful to me in my life."


2. They Were "Just Friends"

As co-stars, Ben Affleck and Jennifer Lopez were just good friends. After all, she had recently married her backup dancer, Cris Judd. But this didn't stop Affleck from tooting his leading lady's horn. In fact, he went ahead and took out a full-page ad in trade magazines just to express his adoration for her—and what he wrote was enough to melt any cold heart.

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3. He Publicly Gushed Over Her

Although they weren't even together yet, Affleck had some serious feelings when it came to Lopez—and his little ad certainly had some flirtatious undertones: "It has been nothing but an honor and a pleasure to work with you...I only wish I were lucky enough to be in all your movies.” And then he rounded it all out: “With love, respect, and gratitude, Ben Affleck.”

His public gushing certainly stirred the pot. There were rumors about a possible romance between these two—and it didn't take long for the truth to come out.

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4. They Confirmed The Rumors

By the time J.Lo's summer birthday bash rolled around, she had separated from her husband. In fact, she had a brand new man to celebrate with. At her surprise party, Lopez and Affleck were seen cuddling up to one another and even kissing. It was finally time for the tabloids to come out and play—and since then, they've never really left these two alone.

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5. They Became Tabloid Fodder

Two days after the birthday party PDA, Lopez filed for divorce from Cris Judd. After Bennifer made it official, the media went into high alert. Snapshots of these two become pure gold. In August 2002, People magazine spent a whopping $75,000 for photos of the couple galavanting in a Bentley convertible. The cherry on top? A prized photo of the two of them enjoying a sensuous "lip-lock."

As Affleck and Jennifer began to heat up, they also became increasingly self-aware. They knew how much they'd captivated the public's imagination—and had something to say about it. The only problem? It backfired...hard.

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6. The Music Video Went Viral

Who can forget the infamously viral music video for "Jenny From the Block." Not only did it tell the story of the paparazzi's obsession with the couple, but it also gave them exactly what they wanted..and more. The video gave fans an intimate look into the couple's romance. But the video's most sensational moment also became one of Affleck's biggest regrets.

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7. THAT Kiss Was His Idea

Nothing is sexier or more cringe-worthy than Ben Affleck worshipping J.Lo's famed posterior. Yup, in the video for "Jenny From the Block," while sunbathing on a yacht with her, Affleck leans over and plants a smooch on his girlfriend's butt. And even better? This was Affleck's very own idea. It might have seemed like a good choice at the time—but in retrospect, it became a mighty faux pas.

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8. He Had One "Big Regret"

In the years following this statement video, both J.Lo and Affleck began to feel the sting of regret. In fact, J.Lo even tried to get the video removed from MTV, while Affleck called it the "big regret" of the entire relationship. At the time, however, it was all part of their whirlwind romance. Despite criticism, things seemed to be heating up. As we know now, it was all doomed to a messy end.

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9. They Didn't Waste Any Time

Before they imploded, Affleck and Lopez enjoyed a brief but extravagant honeymoon phase. Only months after Lopez ended her second marriage, Affleck was already in planning mode. He wanted a superstar to be his wife–and his proposal needed to fit the bill. In November 2002, he set the scene at his mother's Boston home—and when J.Lo walked in the front door, she couldn't believe her eyes.

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10. He Planned The Perfect Proposal

In an exclusive interview with Diane Sawyer, Lopez described the fairytale proposal: "It’s just a blanket, a quilt of rose petals, all over the whole entire house. So many candles, and vases, bouquets. And my song 'Glad' was playing…I walk in and I was just, like, overwhelmed. I wasn’t expecting it, and I was just like, 'Oh my God.'" But that wasn't the most impressive part.

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11. He Purchased An Unforgettable Engagement Ring

As if this proposal couldn't get any better, Affleck got down on one knee and revealed the ultimate showstopper: a 6.1 carat pink diamond engagement ring from Harry Winston. At the time, Affleck reportedly purchased it for 1.2 million and it certainly stopped J.Lo in her tracks. She later called it "the most magnificent thing I've ever seen." And the intrigue behind the ring didn't end there.

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12. He Spent A Fortune On Her

That massive pink ring became one of the most recognizable pieces of jewelry in Hollywood—and today, it's estimated to be worth anywhere from $2.7 million to $12 million. Affleck turned out to be quite the romantic, explaining that he specifically selected the ring because he wanted his fiancé to "have something that nobody else would have."

Unfortunately, no amount of money would free the couple from the media attention that dogged their every step.

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13. They Claimed To Be Innocent

Considering their rapid engagement, rumors about infidelity began to surface. They insinuated that Bennifer had gotten together while Lopez was still married to Judd. These comments threw them for a loop, especially Affleck, who told Vanity Fair, "That is absolutely not true. It goes against the fundamental code I believe in and live by: being honest, doing things with which I can live, rather than be ashamed of—doing esteemable things."

Little did Bennifer know, this was only the calm before the storm.

Bennifer FactsShutterstock

14. Disgusting Rumors Begin To Surface

Their bliss began to nosedive during the summer of 2003. Mere hours after their personal Dateline interview dropped, so did another stunning revelation. Allegedly, Affleck had been spotted at a Vancouver strip joint, with some sources claiming that he'd cheated on J.Lo with another woman. The rumors began spiraling, and there were even references to taped evidence.

It was a real eye-opener for the couple—and it was only a matter of time before the perils of Hollywood began to poison everything.

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15. They Called Their Wedding Off

The anticipation that revolved around Affleck and Lopez's wedding became akin to a royal affair. But as the big day approached, doubt crept in. Only a day before the ceremony, the couple released a jaw-dropping statement. They had decided to postpone their nuptials. The media had finally gotten under Bennifer's skin, destroying their special day in one fell swoop.

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16. They Almost Had "Decoy Brides"

Unnerved by the constant attention, Affleck and Lopez had even considered implementing "decoy brides" to throw the press off. It drained them of the excitement they were supposed to feel. Their statement read, "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."

For Bennifer, this was the beginning of the end (well...sort of).

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17. They Ended It

By January 23, 2004, the relationship was over—and the headlines were brutal. The Chicago Tribune headline just read, "Dumped." Lopez released a very simple statement about the broken engagement and asked that her privacy be respected. But this left the public with a lot of unanswered questions: Why in the world did this power couple come to such a sudden end?

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18. Their Second Film Was A Disappointment

Affleck and J.Lo made one more film together before breaking up, and they might have been kicking themselves for doing so. Only months after parting ways, their film Jersey Girl hit theatres, and it stunk just as bad as Gigli. The film's failure only echoed the failure of Bennifer. It was finally time to move on, and both actors didn't waste any time.

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19. Within Months, She Married Another Man

In the wake of the breakup, J.Lo found herself floating back to an old flame, singer Marc Anthony. They'd met back in 1999 while collaborating on the song "No Me Ames," and rekindled their love in 2004. In fact, only months after breaking her engagement with Affleck, Lopez married Anthony. She later wrote, "All the heartache and pain of my recent breakup couldn’t have been for nothing, could it? Maybe I had to go through the bad so I could end up with the person I was meant to be with all along."

Affleck, on the other hand, had a romance as well. For the media, his new lady was a glaring clue as to why Bennifer imploded in the first place.

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20. His New Girlfriend Sparked Rumors

In the autumn following J.Lo's marriage, Ben Affleck stepped out with his new girlfriend and old co-star, Jennifer Garner. It didn't take long for everyone to do the math. Although the couple had originally met on the set of 2000's Pearl Harbor, they'd become much closer on the set of 2003's Daredevil. This only meant one thing.

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21. He Fell In Love With Another Jennifer

In an interview with Playboy, Affleck confirmed what everyone suspected: He'd fallen in love with Garner in the summer of 2002 while filming Daredevil. He told them, "We met on Pearl Harbor, which people hate, but we fell in love on Daredevil. By the way, she won most of the fights in the movie, which was a pretty good predictor of what would happen down the road—my wife, holding swords and beating the living s--- out of me."

It certainly sounded romantic, but in reality, it was all a big mess.

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22. They Sparked Scandalous Rumors

At the time, Affleck was still with J.Lo, and Garner was married to actor Scott Foley. In fact, Bennifer's romantic engagement came after this summer of action hero love. But if you take a closer look, the truth of it all starts to bubble to the surface. While still attached to other people, Affleck and Garner were guests on Dinner for Five—and their interactions were so flirtatiously charged, it was hard not to notice.

Bennifer FactsDinner for Five, IFC

23. He Couldn't Resist Her

While watching Garner and Affleck chat on Dinner for Five, some viewers sensed some romantic tension between the co-stars. A writer for Vulture commented that, during one scene, Garner gazes at Affleck with "such a genuine look of gratitude and affection, it still makes me a bit uncomfortable to see it on television." Turns out, sometimes, the rumors are correct.

Almost a year after going public, Affleck and Garner married in a private, understated ceremony. At this point, nobody could have predicted that Affleck and Lopez would one day reunite.

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24. They Moved On

For the next decade, Affleck and Lopez worked hard on their marriages. By 2009, Affleck had two daughters, Violet and Seraphina, while Lopez had twins, Max and Emme. On the surface, everything seemed to be going well—but behind the scenes, demons stalked both Affleck and Lopez. Before they knew it, their individual struggles had led them straight to the deep end.

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25. His Vices Poisoned Everything

Sadly, Ben Affleck has had a long-standing drinking problem that can be traced all the way back to his teen years. During his marriage to Garner, he continued to struggle with addiction, as well as anxiety and depression. In fact, in his fight to stay sober, there were periods of the actor's life where he'd drink until he "passed out" every night.

Throughout his career, Affleck has been dragged through the mud for his relapses and stints in rehab—and it may have been a factor in the collapse of his marriage.

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26. J.Lo's Divorce Shocked Everyone

Three years after Lopez and Anthony welcomed their twins, they shocked the world by announcing their divorce. In her book, Lopez wrote that she told her husband, "This is not working. You know it's not working. We're not living like a family, and I don't see how things are going to change. Neither of us is happy, and the kids are wondering what is going on. I think we should move on with our lives."

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27. Everyone's Breaking Up

Miraculously, Lopez's split with Anthony was one of the most amicable and successful breakups imaginable. They still had a deep love for one another and, since then, have maintained a close friendship. But while her own marriage dissolved, so was her ex-fiancé's relationship. In 2015, Affleck and Garner announced their separation—and it absolutely cut the actor to his core.

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28. It Was His "Biggest Regret"

After a decade of declaring his undying love for Jennifer Garner, Ben Affleck had to accept that his marriage was finally over. He even called their split "the biggest regret of my life." Although he knew this was the right decision, he couldn't deny that the "painful experience" was one of the hardest challenges of his life, especially with three kids involved.

With both Affleck and Lopez released from their long-term relationships, the press waited in the wings with bated breath.

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28. He Was Always The One That Got Away

In 2016, Jennifer Lopez spoke to People magazine and commented on her brief engagement with Ben Affleck. What she had to say was more than a little prophetic: "I think different time, different thing, who knows what could’ve happened, but there was a genuine love there." Unfortunately, both Affleck and Lopez had another round of heartbreak to face before finding their way back to one another.

Jennifer Lopez And Marie Osmond Launch 'Put Your Money Where The Miracles Are' CampaignGetty Images

29. She Had ALL The Bling

After her split with Marc Anthony, J.Lo's next big romance was with former Yankee, Alex Rodriguez. After dating her for two years and watching Lopez grow close with his daughters, Rodriguez decided to pop the big question. To stand out from her former suitors, he certainly went the extra mile, proposing to her with a $1.8 million emerald-cut engagement ring.

Meanwhile, Affleck himself began moving forward. However, his next romance shocked everyone.

Alex RodriguezShutterstock

30. He Fell For Another Co-Star

A year after Lopez's engagement announcement, Affleck found himself falling hard—and he was not complaining. On the set of the romantic thriller Deep Water, he met the gorgeous up-and-comer, Ana de Armas. In the film, the stars play a married couple, but surprisingly, they kept things professional until filming paused due to the pandemic.

Once they had time away from work, however, things really started heating up.

Bennifer FactsShutterstock

31. He Followed Her Home

Nothing says romance like going on a trip to your girlfriend's home country. On a trip to Havana, Cuba, Affleck and de Armas were spotted looking very much in love. According to eyewitnesses, the Cuban actress showed him all her favorite spots, and Affleck even conversed with her in her native tongue. This set the scene for a quarantine like no other.

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32. He Performed For The Paparazzi

During quarantine, Affleck and de Armas became the paparazzi's dream team. They had no qualms about stepping out together and showing off some PDA. Affleck seemed completely smitten with de Armas: There were Instagram posts, selfies, public smooches, and lavish birthday gifts. But that wasn't the best part.

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33. She Blew Him Away

As much as Affleck doted on de Armas, he also respected her as an actress. The first time they sat down to read lines together, de Armas blew him away. He later commented on her performance, saying, "Not only does she know how to do it with ease, she also manages to surprise you in every shot. Her talent is infinite." But you know what was not infinite? Their relationship...

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34. He Threw Her In The Trash

After one year of dating, Affleck and de Armas amicably parted ways. However, leave it to Affleck to expose their breakup in the most hilarious way. Over the summer, his kids had played a prank on him, using a large cardboard cutout of the Ana de Armas. Sadly, onlookers spotted the very same cutout stuffed in Affleck's trash.

Affleck may have been heartbroken all over again—but don't worry, fate was about to step in.

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35. The Cheating Rumors Poisoned Everything

While Affleck enjoyed his summer fling/quarantine with de Armas, Lopez had her own struggles to attend to. Because of coronavirus, her lavish wedding had been postponed multiple times. Unfortunately, things went from bad to worse. At the start of 2021, cheating rumors about Rodriguez and Madison LeCroy were everywhere.

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36. Another One Bites The Dust

No matter how hard she tried, Lopez couldn't escape the press. They published inaccurate articles and even announced her split with Rodriguez before she'd actually confirmed it. But as it turns out, the media's speculations were correct. In April 2021, the couple released a joint statement—and it was the nail in the coffin: "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."

On the heels of grief and heartbreak, the stage was finally set for Bennifer to make their glorious comeback.

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37. They Claimed To Be Just "Friends"

On April 30, 2021, Ben Affleck and Jennifer Lopez shocked the world. Affleck had been spotted visiting her LA mansion on multiple occasions. After 17 years, this unforeseen reunion became the perfect tabloid fodder. Of course, Bennifer fended off the rumors by citing their longstanding "friendship." And according to some sources, that's exactly how it all began.

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38. He Reached Out To Her

There's nothing like two single "friends" reconnecting and bonding over their failed relationships—but for Affleck and J.Lo, it meant so much more. Allegedly, it was Affleck who decided to reach out to her, with one source saying, "They picked up where they last left off and are enjoying each other’s company right now." Suddenly, the impossible seemed possible.

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39. Bennifer Is Back

For the next month, this tentative couple kept the press on its toes, with everyone on the lookout for a much-anticipated kiss. And then, it actually happened. On June 13, 2021, a photograph of a sultry Bennifer lip-lock surfaced. They'd attended Lopez's sister's 50th birthday and shamelessly packed on the PDA, kissing and holding hands beneath the table.

And once these two started, they just couldn't stop.

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40. She Showed Him Off On Social Media

By the time J.Lo's own birthday rolled around, she knew exactly how she wanted to spend it: Wrapped up in Ben Affleck's arms. There was no turning back now. She even took to Instagram to make it official, welcoming Affleck to her social media via a snap of the sun-kissed couple making out. Fans swooned for Bennifer—but this was just the beginning.

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41. They Aren't Afraid Of The Press

Although the voracious press was one of the reasons Bennifer failed the first time around, the couple navigated the attention with the ease of seasoned pros. In fact, they gave the paparazzi exactly what they wanted. In July 2021, Affleck and Lopez enjoyed some time on a yacht in Mexico. The entire scene was a nostalgic throwback to the infamous "Jenny From the Block" video—and then Affleck did something that made jaws drop.

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42. They Recreated THAT Infamous Bennifer Moment

Cuddled up to his old flame, Affleck decided to unintentionally (or intentionally) recreate his scandalous music video moment by placing his hand on J.Lo's perfect posterior. It may have been his "big regret" back then, but it certainly didn't seem that way now. Nope. Bennifer was full steam ahead. In the following weeks, the proof was definitely in the pudding, with Lopez rocking a necklace that spelled out one tell-tale word—"BEN."

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43. It Was A Fairy Tale Come True

At the 2021 Venice Film Festival, Ben Affleck and Jennifer Lopez stepped onto a red carpet together for the actor's new film, The Last Duel. It had been a whopping 19 years since their very first red carpet appearance—and to see them together again, well, it looked like a fairytale love story come true. Bennifer was finally back and hotter than ever, their chemistry sizzling in every photo.

But as jubilant as the press was to report on this couple all over again, they were also on the hunt for drama. One wrong move and the gossip mill would be out for blood.

jennifer-lopez-and-ben-affleckElle US

44. He Put His Foot In His Mouth

Right when things seemed to be going smoothly, Ben Affleck placed a toe out of line. Or more accurately, he said the wrong thing. In an interview with Howard Stern, he confessed that he'd felt "trapped" in his marriage to Jennifer Garner. But he didn't stop there. While contemplating what would have happened if he'd stuck out the marriage, Affleck said, "We probably would’ve ended up at each other’s throats. I probably still would’ve been drinking." Bad move Ben, bad move.

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45. He Got Torn Apart

It didn't sit so well with fans that Ben Affleck attributed his marriage to Jennifer Garner as a reason for his addiction issues. The press hung on to this negative tidbit with all their might, even claiming that his comments enraged Jennifer Lopez. However, Lopez denied the rumors, fully supporting Affleck. With the criticism weighing heavily on his shoulders, the actor had no choice but to respond.

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46. He Tried To Make Amends

In an interview with Jimmy Kimmel, Affleck tried to remedy his comments by saying that they'd been taken out of context: "[I] would never want my kids to think I would ever say a bad word about their mom." Of course, fans were keen to praise Jennifer Garner for always keeping her private life private—and for never saying a bad word about her ex-husband.

Bennifer FactsJimmy Kimmel Live!, ABC

47. This Wasn't Their First Time At The Rodeo

Although some negative press might have really stressed out Bennifer 1.0, Bennifer 2.0 took it all in stride. Despite the criticism, the couple continued on their merry way. Most recently, Affleck really leaned into his romantic side for Valentine's Day. He didn't quite top the pink diamond sparkler from the 2000s—but he did give Lopez something that "seriously melted" her heart...

Bennifer FactsGetty Images

48. He Made Her A Nostalgic Valentine's Day Present

Some might call it cringeworthy and some might call it romantic, but Ben Affleck injected every ounce of feeling into his Valentine's Day present for J.Lo. He made a video montage of all their special moments together, mostly taken from their 2000s romance. And the cheesy cherry on top? He set it to her new song, "On My Way." Whether you hate the video or not, it doesn't really matter because Lopez adored it.

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49. Their Reunion Was A Surprise

Jennifer Lopez gushed over Ben Affleck's sentimental montage: "Watching it made me think about the journey of true love, it’s unexpected twists and turns, and that when it’s real, it actually can last forever." At this point, everyone's just happy that J.Lo's happy, and by all accounts, she seems to be settling into cloud nine. Her reunion with Affleck completely surprised her—but now, she's more equipped than ever to deal with the tabloids and the criticism.

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50. Bennifer's Ready To Do It Right

In an interview with Rolling Stone, Jennifer Lopez reflected on her tumultuous journey back to Ben Affleck—how she had years to learn from past mistakes: "We feel like what we found again is so much more important, and how we protect that and how we live our lives—what to share, what not to share—is the balance that we have now, the benefit of experience and the wisdom that we gained over the years."

Bennifer FactsGetty Images

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13,

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