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Jennifer Lopez’s Dating History: Husbands, Boyfriends and Fiancés

If you haven’t already realized, Jennifer Lopez and Ben Affleck are officially back together, resulting a collective jaw-drop from around the world. The two dated for three years back in the early 2000s, from 2001-2004, and starred in multiple movies together, from Gigli to Jersey Girl.  In 2016, Jen did say to People magazine, “I think different time, different thing, who knows what could’ve happened, but there was a genuine love there.”

Turns out Jennifer Lopez can tell the future. We have never been more excited to see Bennifer back together, but before we dive into that, let’s take a look at J. Lo’s long and drama-filled dating history. 

1. Ojani Noa 

J.Lo got married to produce Ojani Noa in 1997, but they divorced just 11 months after. In 2007, there was a court order that forced Ojani not to criticize his past love or cast her in a negative light. 

2. Sean Combs

Lopez and Diddy started dating after meeting on the set of a music video (isn’t that how all Hollywood love stories start?) but they broke up 2 years later in 2001. In an interview, Lopez said that he cheated on her throughout the relationship, while the rapper instead refers to Lopez as one of his great loves of all time. 

3. Cris Judd

A lot of people don’t even remember the relationship between J.Lo and Criss Judd, who met on the “Love Don’t Cost a Thing” video. They got married by September 2001, and then, like the 2-year shelf-life of most of Jennifer’s relationships, they had their divorce finalized in 2003. 

4. Ben Affleck 

Here’s where our key player enters. These two were engaged by November 2002, where Ben proposed at his mom’s house in Boston with that infamous pink diamond. A year later, Ben was caught at a strip club in Vancouver, and rumors went around that he cheated on her on that trip. Ben still denies it to this day. Then, Ben and Jen Garner got together, while J.Lo moved on with Marc Anthony and Alex Rodriguez. 

5. Fast-forward to the future

17 years after anything Bennifer-related, on April 30, 2021, sources reported seeing Affleck going back and forth from Jen Lopez’s house in LA. Then in May, paparazzi dropped the infamous photos of the two flying to Montana. A source said they “picked up where they last left off”. Most recently, on May 24, 2021, the two worked out together at a Miami Beach gym, sharing a smooch with ‘intense chemistry between their separate workout sessions. A source says they’re “full-on dating” and can’t wait to see where it goes. Neither can we!

6. Marc Anthony 

This was Lopez’s longest relationship. She shared twins with Marc, and even though they stayed together from 2004-2011, J.Lo admitted that she knew “very quickly” that their marriage wasn’t meant to be. Since the two have kids together, they’ve had to learn how to co-parent, but Lopez stated to W magazine in 2016 that after her marriage needed, she felt “resentment, disappointment, and anger.”

7. Beau ‘Casper’ Smart

Smart was basically J.Lo’s rebound, and everybody knows it. The singer started dating Casper, a backup dancer of hers, in 2011, only 4 months after splitting from her ex. It seemed like they were fine — she even hired him as the creative director of her Las Vegas residency. But in 2014, it all came crashing down when a gossip site claimed to have evidence of Smart exchanging saucy photos and texts with a transgender model. In 2016 they finally split.

8. Drake

This was a brief and mysterious relationship. Towards the end of 2016, the two mega stars connected. Drake pulled a bunch of classic Drake moves, like transforming an LA church into a makeshift winter wonderland-themed prom. Obviously, they won the Queen and King monikers. But just 2 months later, they ended it, partly due to Drake going on a European tour. 

9. Alex Rodriguez, AKA, A-Rod

This beauty has been engaged so many times, and A-Rod was the most recent one. After two years of dating, Lopez and the baseball player announced that they were engaged. On the athlete’s birthday in 2018, this ex Fly Girl wrote an adorable homage to her beau and “getting to know the real” Alex Rodriguez. 

In 2018, all seemed well — US Weekly reported that the couple was looking to move in together, and had happily merged their families. After COVID-19 hit, the celebs postponed their relationship, reported they were “working through some things” and eventually split up, calling off the engagement and writing in a joint statement saying that the two “work better as friends” and will “continue to work together and support each other on our shared businesses and projects.”