Since stepping into the limelight, Jennifer Lopez’s romantic life has been closely examined. Her enduring relationship with Ben Affleck, along with her rumored involvement with Drake, keeps her list of romantic interests in the public eye. This intrigue has been further enhanced by her ninth studio album, This Is Me … Now, and the related movie-musical. In her work, Lopez reflects on the numerous high-profile relationships that have come before and after her latest romance with Affleck, while also recognizing her inclination towards romance. As she expresses in the trailer for This Is Me … Now: A Love Story, “Whenever someone asked me what I wanted to be when I grew up, my answer was always: ‘In love.’” Below, we explore the timeline of Lopez’s marriages, engagements, and relationships, including her time with singer Marc Anthony and her broken engagement to Alex Rodriguez.
Ben Affleck (2021—2024)
Bennifer astonished fans worldwide when they reignited their romance in April 2021, nearly twenty years after ending their first engagement. Their relationship escalated rapidly, culminating in Affleck and Lopez becoming engaged for a second time the following year. “Did you ever think your greatest dream could become a reality?” Lopez inquired in a special edition of her fan newsletter, On the JLo. “On Saturday night, while enjoying a bubble bath at my favorite place on earth, my wonderful love knelt down and proposed. I was completely taken by surprise, gazing into his eyes, smiling and crying simultaneously, trying to comprehend that after 20 years, this was happening again. I was truly speechless, and he asked, ‘Is that a yes?’ I replied, ‘YES, of course that’s a YES.’” The couple officially married in a surprise ceremony in Las Vegas in July 2022, followed by a more lavish celebration in Georgia the next month. Later that year, Lopez announced the upcoming release of This Is Me … Now, which drew significant inspiration from her rekindled romance with Affleck. “When he returned to my life, I felt an overwhelming surge of inspiration and emotion that just flowed out of me,” she shared in an interview with Zane Lowe for Apple Music. “When I feel good, I create music. I began writing and entered the studio in May, and by August, when we got married, it was complete.” Affleck has also expressed his deep admiration for his wife since their unexpected reunion. “She possesses an incredible understanding of how fashion evolves through culture, influenced by music, sports, entertainment, and dance,” he remarked to The Hollywood Reporter in March 2023. At a red carpet event, he told Entertainment Tonight, “She’s brilliant and supports me in every possible way.” Unfortunately, their second chance soon deteriorated into another breakup, as Lopez filed for divorce in August 2024.
In a 2019 interview with Sports Illustrated, Lopez reminisced about her initial encounter with MLB player Alex Rodriguez at a Yankees game in New York City in 2005. She described the moment, stating, “We shook hands, and there was this strange electricity for about three seconds … Three to five seconds of locking eyes and feeling captivated.” However, it took over a decade for the two to reconnect and begin dating. Lopez recounted in 2017, during a guest appearance on The Ellen DeGeneres Show, “I was having lunch when I spotted him walking by. Afterward, I stepped outside and, for some reason, felt compelled to tap him on the shoulder.” Following that interaction, he texted her, suggesting they go out for dinner, to which she agreed, leading to a pleasant evening together.
Throughout their lengthy relationship, J.Lo and A-Rod made numerous high-profile appearances at events such as the Met Gala, the Golden Globes, the Oscars, and the Grammys. Rodriguez also joined Lopez for her performance at Joe Biden’s presidential inauguration in January 2021. They announced their engagement in 2019, but their wedding plans were delayed due to the COVID-19 pandemic in 2020. In April 2021, the couple revealed their separation. In a joint statement, they expressed, “We have realized we are better as friends and look forward to remaining so. We will continue to collaborate and support each other in our shared businesses and projects. We wish the best for each other and for our children. Out of respect for them, we have no further comments other than to thank everyone for their kind words and support.” At that time, a source for E! News provided insight into Lopez’s decision to end the engagement, stating, “After months of doubt and conflict, Jennifer felt she could no longer trust Alex.”
Drake (2016)
In December 2016, speculation arose regarding Lopez’s relationship with Drake after the rapper was seen supporting her during her “All I Have” residency in Las Vegas. This led to a series of now-deleted affectionate posts on Instagram, featuring images of Lopez reclining on Drake’s lap and another of them sharing a hug at a party. A source informed E! News at the time, “She’s having fun.” However, Lopez addressed the rumors in a 2017 interview on The Daily Show, stating, “Let me clear this up. I am not with Drake.” In 2018, Drake appeared to allude to the conclusion of their brief romance in his song “Diplomatic Immunity,” where he raps, “2010 was when I lost my halo / 2017 I lost a J.Lo.”
Casper Smart (2011—2016)
Lopez commenced a romantic relationship with Casper Smart, who served as a backup dancer for her, shortly after her separation from Anthony in 2011. A source informed People that her relationship with Smart, who is 18 years younger than her, was described as “a fun fling” and “not intended to evolve into anything serious.” The couple experienced a tumultuous on-again, off-again relationship before ultimately ending things in 2016. While initial reports suggested that the breakup was amicable, a later insider revelation to People indicated that Smart had been unfaithful to Lopez. “She ended things because he cheated on her and was caught,” the source stated. “This occurred two years ago, and he assured her it would never happen again, but once it did, she was finished.”
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