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.
Old friends: Jennifer dated Diddy from 1999–2001, before breaking up due to his alleged infidelities. He was with her when she wore her iconic Versace dress to the 2000 Grammys
Diddy added that he ‘absolutely approves’ of her then-boyfriend A.Rod and added, ‘He’s a great guy.’
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.