If Jennifer Lopez Is Seeing Exes Again, Diddy Wants His Shot

If you had asked us months ago — maybe after Jennifer Lopez's first rumored split with A-Rod in March, maybe after they called off their engagement, maybe when they finally confirmed their split — which one of Jennifer Lopez's exes we could see her getting back together with, we probably would have said Diddy.

Dating from September 1999 to February 2001, the pair gave us a relatively short but drama filled entanglement— lest we forget the infamous club shootout. Combined with the iconic '90s/early 2000s outfits that still give us style inspiration and bandana envy (it was Diddy, after all, who was on JLo's arm as she wore the notorious Versace dress for the first time), the two are a quintessential couple of the early 2000s era.

Diddy seems to agree, as he posted a throwback paparazzi photo from his and JLo's relationship on Instagram late on May 27, just to be messy, it seems.

Captioned an innocuous "tbt," Diddy's post has added another thrilling layer to the Jennifer Lopez post-break up drama. Though Diddy didn't even tag Lopez in the photo, it hasn't stopped the internet from interpreting the late night post as an even messier version of a "u up" text, shared with the entire world.

And Diddy is not new to Instagram recklessness. From pioneering the "Diddy Crop" by doing the lord's work and cropping the J*nner sisters out of his 2017 Instagram post to keeping Lizzo from twerking on Instagram live during his "world's biggest dance-a-thon" event in 2020, for better or for worse, Diddy does what he wants on Instagram, consequences be damned.

But the "world's biggest dance-a-thon" event was the site of even more drama when J-Lo participated. The pair of exes danced in sync over Instagram Live as ARod sat in the frame. That didn't stop J-Lo from flirting it seemed, asking Diddy: "Did I teach you that?"

Moments like these, plus mentions of Diddy in recent interviews, are the evidence I would have given if asked which ex J-Lo was most likely to get back together with.

In 2019, Lopez spoke about their relationship during an appearance on The Breakfast Club, saying: "The Puffy era was just kind of a crazy, heightened time in my life. You know, Puffy and I both grew up in the Bronx … He had been in the music business and had all this success; I was just starting and making my first album when I met him. He became kind of a mentor to me at that moment. We had this kind of crazy, tumultuous relationship that ended in a bang."

At the time of the interview, J-Lo was still with Rodriguez. By comparison, their relationship and break up seemed far less tumultuous. "We have realized we are better as friends and look forward to remaining so," the pair told Today in their initial press release. "We will continue to work together and support each other on our shared businesses and projects."

Despite the brief moment of on-again-off-again excitement, it all felt pretty final. But no one could have predicted the drama that would ensue following the split.

It seems like Diddy is using Instagram to say … put me in, coach, and remind J-Lo of the "Puffy era." The drama of Diddy's May 27th Instagram post has also been heightened by recent photos of Jennifer Lopez having lunch with yet another ex … Marc Anthony. The two have a good relationship because they have kids together, but the lunch is raising some eyebrows and even starting some conspiracy theories.

Fans on TikTok who can't get enough of each new development are beginning to speculate if JLo is taking a tour of her exes to get back at ARod in some way. This theory comes after rumors of ARod talking to an ex of his own, despite Roriguez denying the claims.

Yet, despite Diddy shooting his shot over Instagram and her lunch with her ex-husband, Jennifer Lopez seems to be going strong with her current ex-man, Ben Affleck. Though she surprised us all with this particular romantic resurgence, the two seem to be happy together (again).