The 51-year-old hip-hop mogul was pictured holding hands with Jennifer, 51, in the photo while decked out in a gray sweatsuit from his Sean John clothing label.
He simply captioned the photo of the former couple with ‘#tbt,’ but the image lit up social media as fans wondered about his intentions in posting it.
Watch out, Ben! Diddy, 51 posted a throwback photo to Instagram of his two decades–old relationship with Jennifer Lopez, 51, who’s currently dating her former fiancé Ben Affleck
The then-couple seemed to be catching up on some morning reading in the picture, with Diddy carrying newspapers and Jennifer holding a stack of magazines.
She was dressed in a white cable knit sweater in tight jeans with open-toe heels and her hair in a casual bun.
Singer Keyshia Cole commented on the Instagram post by suggesting Diddy was saying, ‘Tell ha, come on home baby.’
The superproducer Timbaland let the photo do the talking and simply posted wide-eye emojis, while Diddy’s son King Combs saluted his dad, calling him a ‘Killaaaa’ and adding wave emojis.
Celebrity reactions: Several celebrities and friends of the rap mogul jumped into the comments to salute him for the bold choice in photos, while one person even joked, ‘Bye Ben’
Feeling nostalgic: The paparazzi snap was taken in December 2000 after the pair dined at The Ivy in West Hollywood
New/old love: Jennifer has recently reunited with her former fiancé Ben Affleck, and the two have been glimpsed together on getaways to Montana and Miami following her split from Alex Rodriguez; seen together in 2003
Diddy’s son Justin Dior Combs also seemed to salute his father for the post with multiple fire emojis.
The entrepreneur Leon ‘Starino’ Anderson was more blunt in his caption, suggesting Ben’s days with Jennifer might be numbered: ‘Bye Ben.’
The rapper Rich the Kid posted a simple bullseye emoji in his comment, while the singer Ester Dean wrote, ‘Don’t get me excited!!!!’
Diddy’s no stranger to sharing his feelings about his ex, even when she’s in a long-term relationship.
Back in 2019, when she was dating her ex-fiancé Alex Rodriguez, he commented ‘OMG’ when Jennifer posted a busty photo highlighting her outstanding figure and her toned abs.
At the time, A.Rod seemed to mark his territory, as he also commented, ‘Lucky me.’
Not holding back: Back in 2019, Diddy caused a stir when he commented ‘OMG’ on a busty photo Jennifer posted to Instagram that highlighted her outstanding abs
Not to be upstaged: Later in the day, her then-beau Alex Rodriguez seemed to mark his territory by posting his own comment: ‘Lucky me’
Jennifer and Diddy (born Sean Combs) began their relationship in 1999 after they were introduced on the set of a music video.
He accompanied her to the Grammy Awards ceremony in 2000 when she debuted a stunning jungle green dress that plunged well below her navel.
The look, which was augmented with double-sided fashion tap and nude-colored shorts to protect her from wardrobe malfunctions, created a sensation at the ceremony.
In 2017, the rapper told Entertainment Tonight that he thought the dress would ‘really change the game as far as for her and fashion.’
In the same interview, he said the Hustlers star was ‘without a doubt’ one of his greatest loves.
Diddy added that he ‘absolutely approves’ of her then-boyfriend A.Rod and added, ‘He’s a great guy.’
Romantic rivals? Diddy dated Jennifer from 1999–2001, though she’s currently reunited with her ex Ben Affleck, whom she dated from 2002–2004, before calling off their engagement; Diddy seen with Affleck in 2004 at the Deomcratic National Convention
Old friends: Diddy was with Jennifer when she wore her iconic Versace dress to the 2000 Grammys
Their relationship was short-lived, though, with the couple breaking up in 2001.
In 2003, Jennifer claimed to Vibe that the music executive had been unfaithful throughout their relationship, prompting the split.
A December 1999 arrest on a weapons charge may have also harmed the relationship.
Both Diddy and Jennifer were charged with weapons counts after their SUV was pulled over in the wake of a nightclub shooting, and police found a stolen handgun in the vehicle.
The charge against Jennifer was dropped less than an hour after it was announced, but Diddy went to trial.
He was declared not guilty on all counts, though the rapper Shyne, who had also been in the vehicle, was convicted on several counts and sentenced to 10 years in prison.
Dark times: A December 1999 arrest on weapons charges put a strain on their relationship. The charges against Jennifer were quickly dropped and Diddy was acquitted; seen in 2000
Even as Diddy was looking back at a past relationship, Jennifer was seen out in Miami showing off her famous figure and her enviable abs.
The Waiting For Tonight singer was spotted out on her way to a gym session in an eye-catching lavender sports bra and matching high-waisted leggings that accentuate her curves.
She paired the athleisure ensemble with a white-and-brown alligator print handbag and wore a pair of dark aviator sunglasses.
The actress and singer had her long locks tied back in a ponytail to highlight her hoop earrings.
Although she and Ben have been spending time at her home in LA and on their trips across the country, she’s normally based in Miami, where she lives with her twins Emme and Max, 13, whom she shares with her ex-husband Marc Anthony, 52.
Fit figure: Jennifer was seen out in Miami on Monday on the way to the gym. She wore a lavender sports bra and matchign leggings with white trainers and an alligator handbag