Photo: Scott Alfieri
In 2003, Jennifer Lopez released a music video for “Jenny From the Block,” a song that was meant to be a shot to her haters reacting to her extremely public and over-saturated relationship with Ben Affleck. The song’s lyrics tout her relatability, claiming that even though she’s rich, loves fur, and is otherwise far removed from her humble Bronx upbringing, she is still the same as she ever was. Surely part of the video is intended to be self-aware, perhaps satirical: Lopez’s love interest in the video is Affleck, and they seem to take a perverse pleasure in frolicking as the tabloids have captured them. At one point, Affleck unties the straps of his beloved’s bikini as they sit on a yacht, then palms, slaps, and kisses her butt.
Part of the lore of Jennifer Lopez and Ben Affleck’s ill-fated first relationship is that their love took root on the set of the nearly unwatchable 2003 film Gigli, which is about a regular gangster, played by Affleck, and a sexy lesbian gangster played by Lopez, who are enlisted with the task of kidnapping the“mentally challenged” brother of a shared enemy. For anything to flourish from the soil of this production is a testament to its strength. Gigli is a terrible movie, objectively bad for both parties, who, in the early 2000s, were at the height of their respective careers. Incredibly, Lopez and Affleck were paid an awful lot of money for this film. “Mr. Affleck and Ms. Lopez’s combined fees reportedly ran close to $25 million, and they earn their money by hogging as much screen time as possible and uttering some of the lamest dialogue ever committed to film,” wrote A.O. Scott in the New York Times.
Jennifer Lopez was not yet who she is today, but she did have a music career that some might call impressive. At a year or so out of a high-profile relationship with Diddy, Lopez’s music career was at its peak. Her star turn in 1996’s Selena put her in a position to be something close to a triple threat, but Gigli almost tanked her career. Affleck emerged around the same time as Lopez, starring in Good Will Hunting, a movie that made him an Oscar winner and cemented his place as a star. In 2002, when Gigli was filming, Affleck had yet to enter the sad Ben portion of his life, bleary-eyed and puffy in the backseat of an SUV while his ex-wife, Jennifer Garner, wordlessly passes a grease-stained Jack in the Box bag over her shoulder. Lopez had not yet entangled with Marc Antony or any number of background dancers. They were two burgeoning famous people who just happened to find each other, an unlikely pairing that now, in the context of the paths their fame has taken them, makes a lot of sense.
Affleck and Lopez’s relationship was one of the first big relationships of the 2000s, second in size and star power only to Jennifer Aniston and Brad Pitt, whose marriage ended in 2005, after Pitt fell in love with his co-star, Angelina Jolie, on the set of Mr. and Mrs. Smith. The tabloids ran wild with the fallout from the Pitt-Aniston divorce, but those two did their best to keep their love under wraps. Affleck and Lopez, two bright stars at the peak of their fame, who despite the reviled nature of Gigli, managed to persevere. They lived their romance in the public eye—and it was ultimately their downfall.
It’s crucial to remember that in 2002, when Lopez first fell in love with America’s favorite Masshole, she was at the height of her powers. Her music career was actually big enough to be called one, and she was recently divorced from Cris Judd. Thank god for the brawny, smooth arms of a younger Ben Affleck, who by latching on to Lopez for love, also signed up for two years of intense scrutiny and speculation in the press. Though most would like to forget Gigli, for Lopez, the bad press surrounding it left an indelible mark on her confidence and her career. “I was eviscerated,” she told Vanity Fair in 2016. “I lost my sense of self, questioned if I belonged in this business, thought maybe I did suck at everything.” Her new relationship with Affleck, a match that Lopez said the tabloids called “unlikely,” was perfect fodder for the burgeoning gossip industry, who latched onto their every move. It’s not entirely clear if either party wanted the kind of attention they received when they first started dating, but the paparazzi forced their relationship’s every move into the public’s eye, turning against both parties in equal measure.
In a 2012 interview with GQ, Affleck reflected on the coverage, taking issue with the fact that the tabloids seemed to suggest that the relentless attention was something that he sought out. “I must have touched some specific little place in the consciousness. I don’t believe I didn’t deserve any negative judgment for anything, but it was just way out of whack,” he said. From GQ:
“The most pernicious illusion, myth, was that this is something that this guy wants,” says Affleck. “ ’He’s wanting this much coverage.’ That’s the most unappealing thing that you can say about somebody. And I knew how disastrous it was. It was the last thing I wanted, and I could tell it was damaging me, and I tried to get away from it, but there was still this idea: This is what this guy wants, he’s a shallow guy, a camera whore or whatever. And there was no convincing people that that wasn’t the case.”
Affleck’s reputation leading up to his relationship with Lopez was that of a playboy—hard to conceptualize now, when his image as a sad divorceé chasing the dragon of his youth by dating Ana de Armas has been splashed across the internet for the duration of the pandemic. But in 2002, Ben Affleck was somewhat of a hot commodity, made only hotter by his proximity to Lopez. And their relationship was the sole focus of the tabloids at the time, a fluffy little bonbon that acted as beautiful counter-programming to the nightmare of the Bush era, the war in Iraq, and yes, I’m sorry, 9/11.
In retrospect, some of the details of their past love are a little confounding. In 2002, he took out a half-page print ad in Variety praising Lopez for her professionalism on the set of Gigli—an attempt to prove to her haters that her reputation as a “diva” was incorrect. “I thought I’d write a paragraph saying what a professional, decent person I think she is and how kind she is,” he said. Whether or not this was Affleck just shooting his shot, whatever it was, it worked. Though the ink was still drying on Lopez’s divorce with Judd, the two threw themselves into their relationship with an ardor that might have been genuine, if not a little flashy. Consider the rumor that Ben may have purchased a $100,000, jewel-encrusted toilet seat for his princess in 2003, which he reportedly designed himself. As a present it was perfect tabloid fodder, feeding into the twin narratives that Lopez is a diva and Affleck, a besotted sod of a man who can’t help himself. But, it’s also the kind of gift that might be some sort of inside joke between rich people in love.
Everything about their relationship was over the top, including the proposal. When Lopez sat down with Diane Sawyer in 2002, she further revealed the depths of Affleck’s affection, sharing details about their engagement for the first time in the press. Affleck proposed at his ancestral home in Boston, with candles, rose petals, and vases everywhere, a setup that his mother, who loved Jen, assisted with. The ring was Harry Winston, pink diamond, very rare, and fit for a princess. During this interview, Lopez doubled down on her compatibility with her then-fiancé, saying that even though they might seem unlikely, truthfully they’re very similar. “We’ve talked about this so many times, and we talked about how people kind of see him with… one type of person and me with another type of person,” she told Sawyer. “We’re probably more alike and from the same kind of background… same kind of upbringing and same kind of family and same kind of house.”
In a 2003 interview with Pat O’Brien on Dateline, Lopez and Affleck appear almost sheepish, talking about what was arguably a relatively normal relationship that was catnip to the press. “When did you fall in love?” O’Brien asks, with a seriousness that seems outsized for the situation. “You keep asking that!” Lopez replies, with a bit of exasperation. “You can’t pinpoint it.”
But that is precisely what the tabloids needed: a tick-tock timeline of their relationship that could make sense to the public. The trouble is, relationships aren’t required to make sense to anyone except for the two people in them and Lopez and Affleck eventually caved to the external pressure, even though their relationship seemed like a relatively normal one by any measure. In September 2003, one day before they were set to get married in Santa Barbara, the couple released a joint statement postponing their nuptials due to the relentlessness of the media. From People:“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.”
The couple tried to make it work for a few months after, but eventually split for good in 2004. Lopez married Marc Antony in 2004, and Affleck married Garner in 2005. Both parties continued their lives, always speaking kindly of each other in the press. In 2016, Lopez told People that the love between her and Affleck was “genuine” but that maybe the timing wasn’t quite right. And now, in 2021, it seems like they are ready to give it another shot, thanks to Ben’s quiet and steady email campaign in the wake of Lopez’s broken engagement to Alex Rodriguez, which has finally paid off. According to People, Lopez is “open” to the idea of a relationship with Affleck, but the pair are taking it slowly, just figuring it out together.
Consider their new possible relationship as the best sort of fairytale ending, one that is more realistic and therefore more relatable than their first go. Both parties have arguably grown up, but Ben’s trajectory from skirt-chaser to sad dad to newly-reformed commitment-phobe feels familiar. Perhaps part of the excitement here is that Ben is standing in for every single non-committal man in his 20s and 30s, who all found themselves in perfectly decent relationships that were stable but not exciting—and then ran for the hills. Or maybe the timing really wasn’t right. All of this is speculation, of course, but most likely, Ben and Jen are doing what they were always going to do, and now the time is right.
The nostalgia for the culture of the early aughts is nigh because this is how it always works: fashion and culture are often cyclical . But the resurgence of one of the 2000s’ most prominent famous couples is a welcome respite. Even if you were not a fan of Bennifer then and certainly have no interest in their comings and goings now, there’s something to be said for the simple pleasures of a low-stakes celebrity romance as much-needed distraction.