Little is known about Lopez’s relationship with her high school sweetheart David Cruz, but the two reportedly dated for a decade before Lopez became a household name. “They were high school sweethearts,” a source for People claimed in March 2020, not long after Cruz passed away from heart disease. “He was soft-spoken and kind and he would do anything for Jennifer. You could see her trajectory early on and at the time he didn’t mind seeing her take the lead. He was completely content with that. He just loved her.”

Lopez’s first marriage was with waiter Ojani Noa, with whom she tied the knot in February 1997. Though the marriage lasted for less than a year before ending in divorce in January 1998, the legal drama between the exes persisted long after the relationship ended. In 2007, Lopez won a lawsuit that forbade Noa from publishing a tell-all book about their marriage, and five years later, she won another lawsuit against her ex for shopping around private home videos featuring Lopez.

Following her first divorce, Lopez began a tumultuous relationship with Sean “Diddy” Combs, which lasted for a little over a year before ending in February 2001. “It was the first time I was with someone who wasn’t faithful,” Lopez later told Vibe in May 2003, noting that she "never caught" Combs in the act, but "just knew" he was cheating.

Following her 2001 split from Rodriguez, Combs took to IG to post a throwback pic of himself and Lopez, and though fans thought he might be trolling Affleck, Combs said he didn’t intend any ill will. “It wasn’t no trolling involved, that’s just my friend,” he told Vanity Fair in his September 2021 cover story.

Lopez’s second marriage was to dancer Cris Judd, who was one of her former backup dancers. After a whirlwind courtship, the two tied the knot in September 2001, but the marriage lasted for only nine months. In July 2002, Lopez filed for divorce, with a rep for the couple stating “the two will remain friends.” Later, during a May 2003 interview with Vibe, Lopez said, “I loved Cris, still love him, he’s one of the best people. This wasn’t an easy thing to walk away from, but we didn’t have what it takes to make a marriage work.”

Affleck and Lopez first crossed paths in late 2001 on the set of their critically-panned rom-com Gigli, though at the time, Lopez was still married to Judd. However, it wasn’t long after Lopez filed for divorce that Bennifer was born. By November, the couple was engaged, and fans were shocked when the two decided to call off their wedding just days before it was set to take place in September 2003.

“When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realized that something was awry,” they said in a statement. “We began to feel that the spirit of what should have been the happiest day of our lives could be compromised.” In January 2004, four months after postponing their wedding, they called off their engagement altogether.

Lopez later blamed the excessive media attention for their relationship’s demise. "We didn't try to have a public relationship," she told People in 2016. "We just happened to be together at the birth of the tabloids, and it was like, 'Oh my God.' It was just a lot of pressure... I think different time different thing, who knows what could've happened, but there was a genuine love there." And now it seems they’re going to get that chance.

Though they first met back in 1998, Lopez didn’t start dating Marc Anthony until after she and Affleck split. Both fresh out of relationships, Lopez and Anthony shocked fans when they got hitched in June 2004 before even going public with their romance. Their marriage lasted seven years, during which they welcomed twins Max and Emme in February 2008, and fans were shocked once again when they announced their decision to split in July 2011.

The divorce was finalized three years later in June 2014, and since then, Lopez and Anthony have remained amicable co-parents. "We're just in a really great place, and the kids get to spend time with the two of us more together and see us working together," Lopez said of her relationship with Anthony during a March 2017 appearance on Live With Kelly. "It's just good for the whole family." She also mentioned that she and Anthony are “like best friends.”

Like Judd, Casper Smart met Lopez while working as her backup dancer, and at some point in late 2011, their relationship went from professional to romantic. The two quietly dated on-and-off for nearly five years before news of their split started circulating in August 2016. “It wasn’t anything dramatic and they were on good terms — it just came to a natural end,” a source claimed to People at the time. “They will remain friends and they see each other, but they are not together. It was very amiable.”

12 years after they first crossed paths, Lopez went on her first date with Rodriguez in February 2017, and by May, they hit their first red carpet together as a couple. After just about two years of dating, Rodriguez popped the question in March 2019, and it seemed like they were in it for the long haul. Sadly, the pair confirmed their breakup just over two years later following rumors of A-Rod stepping out with Southern Charm star Madison LeCroy. Luckily, it wasn’t long before Lopez was sparking dating rumors with an old flame.