Jennifer Lopez: A Rollercoaster of Romance
Since Jennifer Lopez finalized her divorce from Ben Affleck in January, she has found herself in a whirlwind of romantic entanglements, including an A-lister, a British comedian, and now whispers of wanting her former fiancé back. Once again, J-Lo, 55, is navigating the tumultuous waters of love with dizzying speed—without a close circle of female friends to caution her to take a breather.
Jennifer and Ben Affleck were married from July 2022 until their separation in January 2025. Just weeks after her fourth divorce, J-Lo was spotted cozying up to Kevin Costner and has recently been linked to Brett Goldstein, the star of Ted Lasso. Insiders suggest that beneath her glamorous exterior, she secretly yearns for genuine friendships but feels lost in how to cultivate them.
In my encounters with the superstar, I sensed a lingering loneliness. She often cycles through friendships, forming unlikely bonds that seldom last. Despite her fame and success, she has never quite embraced the role of a ‘girl’s girl’.
When we first met, Jennifer had just gotten engaged to Ben—ushering in the era of ‘Bennifer’ for the second time. Fast forward two decades, and while it’s clear that J-Lo is on the hunt for her next romantic chapter, sources indicate she feels threatened by other women, leading her to keep them at a distance. This lack of a supportive circle may leave her vulnerable to repeating past missteps.
Recently, she has been seen with movie star Kevin Costner and is rumored to be growing closer to British comedian Brett Goldstein. There’s even speculation about a potential reunion with baseball star Alex Rodriguez, her former fiancé from 2019. Rodriguez is currently dating fitness expert Jaclyn Cordeiro, and even J-Lo’s most ardent supporters may find it challenging to back yet another marriage or engagement.
Hollywood insiders describe her as “in love with love,” “addicted to passion,” and possessing a “constant need for adoration.” A source close to her reveals, “Jennifer has always been absolutely terrified of being single. All her personal dramas are driven by a desire to be in a couple.”
My first encounter with J-Lo was at the New York premiere of her 2002 film Maid In Manhattan. A-list celebrities typically offer little more than a wave and a generic compliment about their craft or co-stars, but Jennifer approached the press pen in a stunning pearl satin gown, radiating joy.
Ben, not in the mood for chatter just weeks after proposing, gave her a quick peck on the cheek before heading inside, leaving her to engage with the press alone. Despite his reticence, she was eager to share her excitement. When I enthusiastically congratulated her, she beamed and asked, “Wanna see the ring?”
She extended her beautifully manicured left hand, showcasing a mesmerizing Harry Winston 6.10-carat radiant-cut pink diamond engagement ring, which had cost Ben an astonishing £1.2 million. I was momentarily awestruck and asked if it was heavy. Instead of dismissing my somewhat naive question, she giggled and offered, “Wanna try it on?”
Holding that magnificent piece of jewelry was an unforgettable experience; it was enormous—about the size of a die—with two trapezoidal white diamond side stones set in platinum on an 18-carat pink gold band. We even shared a lighthearted moment imagining what it would be like if I were to marry a movie star myself.
Yet, since that encounter, it’s been evident that Jennifer’s friendships with notable figures such as Victoria Beckham, Kim Kardashian, and Meghan Markle have all been fleeting. She has also made disparaging remarks about many renowned women, including Winona Ryder, Gwyneth Paltrow, Madonna, Mariah Carey, Melissa McCarthy, and Salma Hayek. “She is threatened by glamorous women,” a source disclosed. “They terrify her.”
As Ben seems to be rekindling his relationship with his down-to-earth ex-wife Jennifer Garner, J-Lo finds herself with a stark absence of wise women to turn to. Recently, she has had falling outs with actress Leah Rimini and has experienced rifts with her sisters Leslie and Lynda Lopez, particularly regarding her tumultuous relationship with Ben. She even parted ways with her longtime producing partner Elaine Goldsmith-Thomas after the release of her ill-fated film This Is Me Now, which made Elaine “uncomfortable.”
Bitter Feud
This extravagant project had already raised eyebrows within J-Lo’s team, who tried to steer her away from pursuing it. Nevertheless, she forged ahead, pouring a staggering $20 million into it. Following that, she released The Greatest Love Story Never Told, a cringe-worthy documentary chronicling her 20-year romance with Affleck. The critics pounced, her subsequent concert tour was canceled due to poor ticket sales, and a rumored Las Vegas residency never came to fruition.
J-Lo has thrown shade at Gwyneth by questioning her relevance in Hollywood: “Tell me what she’s been in? I swear to God, I don’t remember anything she was in. Some people get hot by association.” She even belittled Madonna’s acting skills, stating, “Do I think she’s a great performer? Yeah. Do I think she’s a great actress? No.”
Rival Stars
A notable falling out occurred with rival Latin star Salma Hayek. J-Lo was incensed when Salma claimed she had been offered the role Jennifer ultimately played in the 1997 film Selena. “We’re in two different realms,” J-Lo commented. “She’s a sexy bombshell, and those are the kinds of roles she does. I do all kinds of different things.”
In addition, she asserted that she had turned down the role that went to Salma in the rom-com Fools Rush In in favor of starring in the less successful film Anaconda.
Meanwhile, J-Lo has oscillated through four tumultuous marriages, all with a notable absence of bridesmaids or hen parties. She first tied the knot with waiter Ojani Noa in 1997, but that marriage lasted only 11 months. She then married dancer Cris Judd in 2001, but they divorced after just nine months.
Jennifer’s third marriage to Marc Anthony began in 2004, shortly after her first engagement to Ben Affleck had ended. They share twins, Max and Emme, but their divorce was finalized in 2014 after years of ups and downs.
After that, she dated former New York Yankees star Alex Rodriguez, whom she was engaged to until their split in 2021 amidst infidelity rumors. Finally, she became Mrs. Affleck in 2022, but the marriage ended in a blaze of embarrassing publicity in less than two years.
‘Giddy’ with Love
This week, Ben spoke out about their split, claiming there was “no scandal, no soap opera, no intrigue… It’s just a story about people trying to figure out their lives and relationships in ways that we all sort of normally do.”
Jennifer has often been compared to Elizabeth Taylor, who famously married eight times, twice to the same husband, Richard Burton. She has openly admitted to always searching for her perfect match, confessing, “The thing I’m most afraid of is being alone, which I think a lot of performers fear. It’s why we seek the limelight—so we’re not alone; we’re adored. The fear of being alone drives my life.”
Jennifer Lopez’s Relationship Timeline
- Ojani Noa: Married Cuban waiter Ojani Noa on February 22, 1997, but divorced less than a year later.
- Sean Combs: Dated record producer and rapper Sean Combs for two years from 1999 to 2001.
- Cris Judd: Married backup dancer Cris Judd on September 29, 2001, and divorced less than a year later in June 2002.
- Ben Affleck: Engaged to actor Ben Affleck in November 2002; their wedding was postponed in September 2003, leading to a split in January 2004. They rekindled their romance nearly 20 years later in July 2021.
- Marc Anthony: Married longtime friend Marc Anthony in June 2004; they share twins, Max and Emme, but divorced in 2014.
- Casper Smart: Had an on-and-off relationship with backup dancer Casper Smart from October 2011 to August 2016.
- Alex Rodriguez: Began dating A-Rod in March 2017, got engaged in March 2019, but ended their engagement in April 2021.