Sean Combs chose chaos by posting a throwback photo with Jennifer Lopez

You know how I keep talking about how 2021 is some kind of time loop and we’re getting all this vintage gossip from 2002-2007? It’s true. But somehow we skipped the late ‘90s/pre-9/11 gossip and that was a fun and dumb era as well. So while Ben Affleck and Jennifer Lopez are banging like it’s 2003, Sean Combs would like to be included in this narrative. Sean (Puffy/Diddy) posted one of the best and shadiest throwback-Thursdays ever: a vintage shot of himself and Jennifer Lopez when they were dating.

Sean and J.Lo dated from fall 1999 to February 2001. They were an It Couple the entire time, and it was the first time Jennifer really was part of a power couple like that. Her first marriage, to Ojani Noa, crashed and burned in a year, and she was single by the summer of 1998. I don’t remember Puffy and Jen’s meet-cute, it was just like, one day they were together and they were all over the place. Her first album was a smash, she wore the iconic Versace dress to the Grammys, they were pap’d together all over New York, and then the incident at the nightclub in December 1999. That photo of Jennifer looking broken in a police station. The disappearing weapons charge. Puffy’s tearful statement that he would never put Jennifer in any kind of bad situation. Soon after, their relationship was over.

Like many of her exes, Puffy seemed hung up on her for a while after they broke up. While “Bennifer” was much bigger than Puffy & J.Lo, they too burned really bright. I do think that they’ve stayed friendly too – I don’t recall Sean ever saying a bad word about her and she’s always said nice things about him. Still, I have to admire Sean’s love of gossip. He chose chaos and that’s always fun!



Photos courtesy of IG, Avalon Red.

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66 Responses to “Sean Combs chose chaos by posting a throwback photo with Jennifer Lopez”

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  1. josephine says:

    I guess he figured since she’s revisiting ghosts from the past, he’d throw his hat in!

    • Seraphina says:

      🤣 Good One!

    • Lua says:

      There are some interviews where he’s quoted as wanting her back and she’s the one that got away. It’s not just a love of chaos, he’s trying to get back in 😛

    • PlainJane says:

      All I hear is that song, “…I hit it first…” running through my mind and I can’t figure out why.

    • Ronaldinho says:

      Do you remember the Covid internet dance party he threw – my details are mad as my brain is mush – J-Lo came on and they were virtual dancing together
      The chemistry between them still was wild
      A-ROD just smiled in like an old dad

  2. Jan says:

    JLO dumped Puffy after he was arrested, I can’t remember if it was a shooting, he was carry a gun and she was in the Limo with him.

    • Seraphina says:

      Yes, Jan. It was some scuffle at a club late at night and guns were involved. Not sure what and how they were involved but yes she did dump him – like a hot potato. She was being being called out by Hispanic audiences that she was supposed to be a positive influence and not making headlines like that. JLo is all about her image – poor Ditty.

      • Darla says:

        Poor Ditty? Was she supposed to wait till she caught a bullet? Any man I am with, I find out he’s got a gun, or god forbid, there is a gun “scuffle”, I’m outta there.

      • Seraphina says:

        Darla, I know it can be difficult to pick up on in written comments (since tone is lacking) but that was sarcasm on my Poor Ditty comment.

      • Darla says:

        LOL, really? I’m so sorry. I usually do get sarcasm. I apologize Seraphina.

      • Sue says:

        But she didn’t dump him right away. I know this because I remember her “MTV Diary” where she made it a point to be filmed shushing everyone while Sean’s press conference was on tv and he was declaring his innocence.
        It’s so weird the things you remember.

      • smcollins says:

        I remember the incident was used for an episode of Law & Order, with Kerry Washington as the famous actress dating the famous Hip Hop artist. It added a plot twist of her actually being the shooter.

        Fun side note: Brad Pitt’s name was dropped as her last movie co-star to give reference to her fame & popularity. Ahhh…memories 😉

    • Myjobistoprincess says:

      That was crazy. But guys like Jlo because she is a good person. They keep things civil after they breakup because I dont think she’s ever done anything bad to them, but the contrary is true, and with so many years gone by, the guys are now more mature and are wiser to know they were stupid and put her through things she didnt have to.

  3. Cait says:

    Oh man I am here for this vintage gossip revival!! I’m back in my early 20s and it’s a beautiful thing 😁 Diddy (if that’s his most current name), and JLo were HUGE. She did one of those diaries on MTV at the time she wore the Versace dress. Those were the golden days of celebrity gossip, before the property crash, when people were excessive and shameless and everyone mutally pretended there were no problems.

    • StormsMama says:

      His newest name is LOVE ☺️

    • EveV says:

      I hear you on being back in my early 20’s before the property crash and life was good 🙂
      Celebrity gossip was about who was shagging or cheating on who instead of who was assaulting people. Ah, simpler times back then.
      Anyways, yes Diddy, you let a fabulous woman get away.

  4. SarahCS says:

    I’m loving this time machine. After the last few years I am here for this!

  5. detritus says:

    These dudes soooo thirsty for JLO are making my day.

    Should she be the next bachelorette? Who would round out the contestants?

    • lucy2 says:

      Her cast of terrible exes! That would be one helluva show.

    • Laura says:

      There’s something about JLo! They’re all coming out of the woodwork around her like in the movie Something About Mary – also from the late 90’s – early 00’s. I’m am here for this! 🥂🎉🤩👵🏻

  6. Lady Luna says:

    I laughed so hard when I saw his post. He’s just shooting his shot. Lol

  7. D says:

    She did some kind of MTV or similar interview/backstage look at her getting ready for the Golden Globes the year she presented with Matthew McConaughey. They showed her reaction as she drove in the limo and spotted the million posters Puffy put up all over LA for her to see that said “I Love You” or something like that. It was crazy and her reaction was like “Oh, that’s nice.” She broke up with him soon after. He was super into her.

  8. Peanutbuttr says:

    Diddy is my fav JLo ex. They were that power couple that actually radiated power.

    • Seraphina says:

      I always found Diddy and JLo way more interesting than Bennifer. Maybe it’s because with Diddy they were a “music powerhouse” and with Ben she tried to create Hollywood jetset glamour. Whatever the case, I am here for a revival of Battle of the Exes starring JLo.

  9. Eleonor says:

    When JLO did the carpool Karaoke (which was really fun!) she throw a blind item about one marriage proposal she refused, my take it was Diddy, so I think he has a soft spot for her.
    I love vintage gossip!

  10. Truthiness says:

    JLo was disrespected so badly by ARod, I’d love to see all of her exes post throwbacks.

    • LaurenMichelle says:

      Exactly! It’s very telling that her Exes hold her in high regard, or at least pretend to. It’s a J-Lo celebration! Meanwhile,, A-Rod is promoting his man concealer. No one seems to be supporting A-Rod, not even his children. I think J-Lo went through hell with A-Rod, and I am glad she is rid of him.

  11. Delphine says:

    The gossip gods are being super generous right now. Did not see this coming but it just made Bennifer a lot more interesting.

  12. Nev says:

    In a gossip way she won now. She’s the desirable one and is in the power seat. Thanks for the play Diddy hahahhahaha
    She’s gorgeous in these pics.

  13. TheOriginalMia says:

    I liked her with Puffy. Then the nightclub incident (that spawned a L&O ep with a young Kerry Washington) and they were done. He chose chaos and it was good fun on Twitter.

  14. Imogene says:

    lolll this headline sent me


    Diddy trying to start some s–t.

    Also, stray observation: In that top pic, Jennifer is wearing a heavy turtle neck sweater, thick jeans, and then these flimsy ass bare toe shoes. Her poor feet must have been **freezing**.

  16. Watson says:

    Duffy has an awesome sense of humour! This was hilarious

  17. LaUnicaAngelina says:

    Gotdamn, I’m here for this ish. I love it. My love for celebrity gossip started in my teens in the latter half of the 90s. I’m 100% down for all of this!

  18. lowe says:

    Jennifer was actually in his Been Around the World music video in 1997. it was in a dream sequence where they dance together and you could already sense the sexual tension and chemistry then.

    • ReginaGeorge says:

      Hi song “Senorita” was totally about her. The lyrics “Mami ven aqui. I wanna be you Papi Chulo can’t you see.” LMAOO. He was already looking to court her around that time. But I believe she was dating Marc Anthony for the first time around at that point. Then she dumped Marc for Puffy and the rest was history.

  19. ReginaGeorge says:

    Jlo and Diddy were huge. I think they were just as big as Bennifer, especially in the hip-hop circles and with way more opulence because both Jen and Puffy loved to be flashy and ate up the attention. They were the first hip-hop powercouple before Bey and Jay Z.

    Somehow Jamal “Shyne” Barrow had to take the rap for the shooting at the club and his career was over before it even really started. He was being compared to Biggie because they had a similar sound and flow.

    I remember ALL of the sad love songs Diddy put out after their breakup. He tried hard to get her back but she was over it. It was glorious

  20. K says:

    This is a fabulous menage a trois. Diddy is a bad ass for this.

  21. Midge says:

    Oh I love seeing these old photos of JLo with her old face. She was so gorgeous. She still is, but has all the little tweaks that celebs get. And I love that she’s the one that got away.

  22. Darla says:

    Did anyone watch the Friends reunion? I was so surprised to hear that David and Jen had a real thing for each other early on? But were both involved with other people. It made me wonder, since he’s now divorced, if Ross and Rachel actually got together in real life, would it be as big a deal as Bennifer part deux? I know I’d be really into it.

    • detritus says:

      Love it. Some old and add some new bad for her contenders

      Cheating Back Up Dancer
      Surprise guest – Marc Antony?

      Pete Davidson
      Channing Tatum
      Regé-Jean (sorry to his lady this is fantasy casting)
      And Hot Felon

      • detritus says:

        Wow weird reply jump, sorry! Meant to go well above

      • Truthiness says:

        JLo fell for Pete Davidson in a snl skit, somebody could just pull a screenshot 😂😂😂

        Marc Anthony, we’re looking at you, it’s time to ante up a throwback 👀

      • Jules says:

        Hot Felon, dying laughing

      • Emma33 says:

        Hot Felon!!! I’d forgotten about him! Genius. He would be in with a chance.

  23. Becks1 says:

    HAHA I love this. “he chose chaos” yes he did and its fun!

    This is the kind of great gossip we all deserve after the past year.

  24. DiegoInSF says:

    Lol she won by a mile, she’s so desirable and all her exes pine after her for years on end. Arod who?

  25. Marigold says:

    I’m def here for this.

  26. Carolnr says:

    She looks like a sexy, Eva Mendes with glasses in this pic!!!!

  27. psl says:

    I picture her calling Diddy and asking him to join this PR party. I find this all so eye roll inducing.

  28. Vanessa says:

    Thank you Jennifer!! We need it!! This is memory lane. No matter what happen with Ben you do it for the fans.

  29. Nomegusta says:

    He’s so messy 😂

  30. Alexandria says:

    So gorgeous so sexy so captivating. Don’t get me wrong J Lol is still hot. But here she doesn’t try too hard. Who wouldn’t want to be with her?

    Millenials really had delicious gossip back then …but also very bad celebrity mental breakdowns.

  31. Peanut says:

    I remember her being quoted after they broke up and it was just a throw away comment but it was good…I think she was looking at furniture and the couch or chair was described as puffy and she said something along the lines of “ugh, nothing puffy for me”.

  32. olliesmom says:

    I had forgotten all about them being together.

  33. Sarcasm101 says:

    This is funny, creepy and intriguing all at once. Lol!

  34. outoftheshadows says:

    Say what you want about J-Lo, she’s an equal opportunity dater. And I honestly mean this as a compliment, because she seems to be truly attracted to the person rather than race, color, or nationality. (I don’t even think they have to be rich because she dated Caspar…)

    I’m definitely here for Puff Daddy/Diddy/Piddy/Duffy/Ditty/LOVE and all his random nicknames bringing out the old school T. Get in that conversation, sir!

  35. Allo says:

    I love how these throwbacks remind us no false lashes back in the beauty day.

  36. Jules says:

    I think they met when she was cast in one of his videos? There was a dance sequence…that’d be their meet cute if I remember right. Oh and I think the song “I Need a Girl” is inspired by her???

    But I definitely prefer Ben and Jen for sure!

  37. nicegirl says:

    What a stunner

  38. Marley says:

    On a side note, those straight-leg jeans she’s wearing are back in style!

  39. incognito08 says:

    A-Rod, Puffy and Ben are scrambling for Jennifer’s affections while refusing to accept the fact that she is, as the kids say, “for the streets”. She just loves ’em and leaves ’em!