While promoting her new romantic comedy Office Romance, Jennifer Lopez has fielded questions about dating coworkers, past and present. “You’re single right now?” Jimmy Kimmel asked her during an appearance on his late-night show last week. “I am,” Lopez confirmed, interrupting Kimmel’s next query to add, “I should have done it sooner.” The studio audience audibly reacted to the admission, an apparent reference to her divorce from Ben Affleck, which was finalized in January 2025.
Bennifer, the portmanteau used by tabloids during her relationship with Affleck, began on the set of Gigli, the 2003 film that may have been the most cursed romantic comedy of all time. More than 20 years later, Lopez declared to Kimmel, “I’ve been doing it all wrong!” adding with a sly smile, “I’ve been doing it all wrong, trust me.”
The exchange felt familiar, like dialogue borrowed from an early J.Lo rom-com, the first of which arrived 25 years ago. Later in the interview, Lopez insisted she’s not looking for love right now. “I’ll meet somebody somewhere one day,” she said wistfully. “If they’re good enough. I don’t know.” Exactly the sort of thing her stoically single characters would’ve said at the start of The Wedding Planner (2001) or Maid in Manhattan (2002). She just hasn’t met Matthew McConaughey’s bespectacled pediatrician Steve, who—oops—is already engaged to one of her clients when they meet-cute. Or Ralph Fiennes’s playboy politician, who will mistake Lopez’s hotel maid for an upper-class single mother staying as a guest.
After Selena (1997) made Lopez a star, and the following year’s Out of Sight established her crackling chemistry with George Clooney from the trunk of a sedan, Lopez set her sights on rom-coms, signing on to The Wedding Planner and Maid in Manhattan. “I felt like all the women in romantic comedies always looked the same way, they were always white,” Lopez told The Hollywood Reporter in 2019. “And I was like, if I can do it and just show that I’m every girl—because I am the hopeless romantic, I am that—I am the single working woman, I was those things. I remember thinking, ‘I need to be the lead in a romantic comedy.’”
Both movies were commercial successes. The Wedding Planner grossed nearly $95 million worldwide on a budget of $35 million, opening at number one at the US box office on Super Bowl weekend. Combined with the success of her second album, J.Lo, Lopez became the first woman to have a number one film and album at the same time in the country. Critics were less enthused, but early New York Times reviews lauded J.Lo in the working-woman-finds-love genre; her Maid in Manhattan performance drew comparisons to Golden Age stars, including Claudette Colbert and Lauren Bacall.
But Lopez’s initial rom-com hot streak came to a very public halt two years later when she and future husband Affleck fronted Gigli, a romantic crime caper that The Wall Street Journal called “the worst allegedly major movie of our admittedly young century.” In the shadow of Bennifer’s real-life relationship drama, Gigli and the subsequent Jersey Girl (also costarring Affleck) both flopped. Lopez and Affleck called off their 2003 wedding three days before walking down the aisle.
When Gigli failed at the box office, “I was eviscerated,” Lopez said in an interview with Vanity Fair in 2017. “I lost my sense of self, questioned if I belonged in this business, thought maybe I did suck at everything.” Plus, Lopez added, “My relationship self-destructed in front of the entire world. It was a two-year thing for me until I picked myself up again.”
Lopez didn’t abandon the genre entirely, but she never found an onscreen counterpart who truly matched her particular skill for romantic comedies—the Tom Hanks to her Meg Ryan, the Richard Gere to her Julia Roberts. She did, however, teach Gere’s listless suburban husband to rekindle his passion with Susan Sarandon in Shall We Dance? (2004). The following year’s Monster-in-Law focused on Lopez and her character’s future mother-in-law, played by Jane Fonda, rather than Michael Vartan, who played her groom.
“Putting Jennifer Lopez in your romantic comedy automatically gets you halfway to a decent movie. The male lead hardly matters,” The New York Times wrote in its review of the largely forgettable Shotgun Wedding (2022). Josh Duhamel, Lopez’s love interest, is “not exactly Clark Gable, but Lopez makes it work. She always does,” the review adds. “Much of the dialogue feels canned and phony in the style of a badly written sitcom. But coming out of J. Lo’s mouth, I believed it.”
Around the mid-aughts, Lopez formed Nuyorican Productions, Inc. with longtime manager Benny Medina. Their first project was another rom-com, Second Act (2018), in which Lopez plays an assistant manager at a Queens big-box store opposite real-life pal Leah Remini as her onscreen best friend.
She followed it up with ultra-meta rom-com Marry Me, starring Lopez as a pop star set to wed her famous fiancé (played by Colombian singer Maluma) in a splashy Madison Square Garden wedding. When she’s left at the altar, Lopez’s character plucks a math teacher out of the audience, played by Owen Wilson, and marries him instead. In real life, Lopez was engaged to former New York Yankee Alex Rodriguez. Speaking to Vanity Fair in 2020 before the film’s release, Lopez admitted that publicly dating Marc Anthony and divorcing him in 2014 following the Bennifer bedlam had left scars. “You’re out there on your own making mistakes, and I made plenty over the years,” she said. “I’ve watched my personal life crash and burn many times, and then have to live with that. People don’t understand how much it hurts to go through these things and to fail in front of the world.”
By the time Marry Me was released in 2022, J.Lo and Rodriguez had called it quits two years into their engagement. And, just like her character, Lopez was already moving on. Nearly 20 years after first splitting, she and Affleck revived their love story in summer 2021, finally making it down the aisle of a Las Vegas chapel the next July. Lopez announced their wedding by invoking her “idol” Barbra Streisand, referencing “Sadie, Sadie Married Lady” (a classic Funny Girl song).
Perhaps inspired by Streisand, who directed herself in cinematic love stories, Yentl (1983), The Prince of Tides (1991), and The Mirror Has Two Faces (1996), Lopez then poured $20 million of her own money into telling her own. In 2024, Amazon released the film This Is Me… Now: A Love Story, inspired by Lopez and Affleck’s second-chance romance, as explored on the album This Is Me…Now, a riff off her 2002 album This Is Me… Then. The visual album (of sorts) raised concerns in J.Lo’s inner circle. “It feels too much like you’re trying to prove something,” former costar Fonda told Lopez, “instead of just living it.” In the behind-the-scenes documentary that accompanied the movie, The Greatest Love Story Never Told, Affleck noted, “I did really find the beauty and the poetry and the irony in the fact that it’s the greatest love story never told. And if you’re making a record about it, that seems kind of like telling it.”
But Lopez has always worn her heart on her sleeve. “It was so painful after we broke up,” she told Apple Music’s Zane Lowe in November 2022. “Once we called off that wedding 20 years ago, it was the biggest heartbreak of my life. I honestly felt like I was going to die.” Lopez said the decision “sent me on a spiral for the next 18 years where I just couldn’t get it right. But now, 20 years later, it does have a happy ending. It has the most ‘would never happen in Hollywood’ ending.”
As foretold by Gigli, neither Bennifer the love story, nor any art born from it, was built to last. Lopez filed for divorce on the two-year anniversary of their wedding ceremony, before it was finalized early last year. “Do you think you’ve truly been loved?” Howard Stern asked J.Lo during an October 2024 interview on his radio show. She paused and responded “no” before switching to “yes,” as she considered if she had “really experienced loving someone. What I learned is it’s not that I’m not lovable,” Lopez concluded. “It’s that they’re not capable.”
It was a vulnerable moment for J.Lo—the kind familiar to anyone who has loved and lost. And for the past 25 years, she has imbued her rom-com performances with similar feelings, as her characters have grappled with insecurity, infidelity, and being underestimated.
Amid the split, Lopez boarded Office Romance, a movie that seems to understand that audiences root for J.Lo the rom-com heroine in part because we root for J.Lo offscreen too. “We saw something in her that hadn’t been written before,” the film’s leading man, Brett Goldstein, told the Associated Press. He and co-writer Joe Kelly created the role of Jackie Cruz—an airline CEO who falls for her recently hired lawyer, Daniel Blanchflower (Goldstein)—to play to Lopez’s strengths. “In her previous rom-coms, she’s always very low-status and aspirational and trying to achieve something. But we wanted to make something a bit more grown-up, where she’s the CEO. She’s achieved a lot, she’s done great, but there is something sort of missing.”
When Lopez received the script, she felt like, “‘I know this,’” she said in the same interview with Goldstein. “You somehow got inside my head and my skin when you wrote this, and I’m going to offer as much as I can to it because I actually know what this is. I understand who this person is.” Indeed, hot off a Gen-Z salute in the viral teen show Off Campus, Lopez gets another kind of tribute with Office Romance—complete with surprisingly steamy yet breezy chemistry between Lopez and Goldstein.
It feels like a freer version of J.Lo, onscreen and off: a Lopez who wields the highly exposed nature of her own love life to remind us that heartbreak is human. Because the woman who got back together with her ex of 20 years, married him in a Vegas wedding, and spent $20 million of her own money to make movies nobody was sure should exist, is perhaps the only kind of person I trust with making a certain kind of romantic comedy.
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