Page Six: Jennifer Lopez ‘always saw Ben Affleck as the one that got away’

Film premiere of 'Gigli'

So many people are trying to figure out the dynamic between Ben Affleck and Jennifer Lopez now, seventeen years after they broke off their engagement and ran into the arms of different lovers. I still think one of the most crucial pieces of information is that Ben once again pursued Jennifer when she was with another man. In the OG Bennifer relationship, she was married to Cris Judd when Ben pursued her. In the Bennifer Revival, she was engaged to A-Rod when Ben made his move and wrote her some kind of passionate love letter, or a series of emails full of love and longing. That sets a tone for the relationship, but it doesn’t define it. Because towards the end of Bennifer in 2004, Ben was a mess, he was boozing, cheating and gambling and begging J.Lo to dump him. But she’s always had a thing about him – she likes sh-t to be entirely on her terms and Ben didn’t give that to her. So was Ben “the one who got away” for J.Lo? Perhaps.

Jennifer Lopez kept a special place in her heart for Ben Affleck after their 2004 split — which made taking him back 17 years later an easy decision, a source told Page Six.

“Jennifer always saw Ben as the one that got away,” the source said. “She was crushed after they broke up, though she felt at the time that she had no other choice but to call off their engagement.”

Lopez, 51, and Affleck, 48, met in 2001 on the set of their box-office bomb “Gigli.” They started dating soon after and got engaged in 2002. However, the power couple known as Bennifer postponed their 2003 wedding at the eleventh hour and separated the next year.

“As hot and heavy as their relationship was, they were on very different paths at the end of it,” the source told us. “Jennifer was ready to settle down and have kids, but Ben wasn’t keen on giving up his bachelor lifestyle just yet. In the end, she got tired of waiting for him to come around — even though it broke her heart to end things.”

Lopez went on to call their split her “first real heartbreak” and credited her future husband, Marc Anthony, with helping her believe in love again.

“Marc came back into my life three days after I should have been at the altar saying ‘I do’ to another man,” she wrote in her 2014 book, “True Love,” of the Latin singer, to whom she had previously been linked in the late 1990s.

[From Page Six]

Ben might be “the one who got away” but for Marc Anthony, Jennifer is “the one.” If she called Marc up today and was like “let’s get remarried,” he would say “okay, I’m there.” My point? I don’t know, that men love J.Lo and J.Lo has options. Even now that she’s Reviving Bennifer, she has options beyond Ben. He knows that too. I’m not sure if Ben knew just how many options Jennifer had back in the day though. Which makes this a retrospective win for him as well, the realization that Jen really was with him back in the day because she adored him, and she’s back with him now because she still adores him. Ben will still find a way to f–k it up though.

J.Lo looking like a million bucks a few nights ago:

Jennifer Lopez celebrates her sister Lynda Lopez's 50th birthday at Craig's

Photos courtesy of Avalon Red, Backgrid.

Related stories

You can follow any responses to this entry through the RSS 2.0 feed.

75 Responses to “Page Six: Jennifer Lopez ‘always saw Ben Affleck as the one that got away’”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. GrnieWnie says:

    Honestly, JLo is really inspiring. I’m kind of trying to recreate this in real life. I want to be surrounded by a long trail of exes who are still falling over themselves to get back with me.

    • Darla says:

      Same!

    • Annaloo. says:

      Totally. SHE’S the one who should be making a vagina candle. It’s amazing how magnetic she is to these men ( Ben, ARod, Marc, Diddy).

      And I’m sure Cris and Casper still pine for her!

      • Eleonor says:

        AHAAHAHAH!!!!! So true!

      • DiegoInSF says:

        Exactly! She needs to make that candle lol 😆 she’s just so incredibly hot and has redefined what aging looks like. She’s such an inspiration!

      • Annaloo. says:

        DEFINITELY redefining age and not even trying. She’s fit, looks sensational, just amazing. Gwynnie can keep her chicken fried chest and vibrator, I’ll have WHATEVER it is Jlo’s having, she’s got the real glow and I don’t even think she’s trying

      • clomo says:

        Annaloo dead @ chicken fried chest

    • Jules says:

      Ha, all I see is two pathetic celebs seeking attention.

    • minx says:

      “The one that got away:” Some Page Six writer asked the co worker in the next cubicle “Hey will you be my ‘source’? ” Like US and all the rest of the tabs, making up quotes from fictitious “sources” that celebrities won’t bother refuting.
      I’m just enjoying the 2021 Bennifer for now and not taking tab headlines seriously.

    • LaurenMichelle says:

      Ben better not mess this up again. There are 5 children involved in this lovefest, not just him. Plus Ben & Jen’s mums! You can make this work if both partners are Committed. My childhood sweetheart contacted me 11 years ago, and I am now married to him. We had both been through painful divorces, and committed to each other that we would be loyal, and no cheating. We are both 53 years old, and love eachother more than we did as innocent children. We didn’t know how special the friendship & connection was when we were young. I believe in reuniting with an EX, but you have to have the same values and a strong friendship too. Lust & romance has never been a problem for Ben; he has an aversion to Loyalty.

  2. Amy Bee says:

    Wasn’t it Ben who broke off the engagement? In the piece it says that Jennifer broke it off.

    • lucy2 says:

      From what I remember, she did the final dumping, but he checked out of the relationship earlier, got cold feet about the wedding, was going to strip clubs, etc, probably to force her to dump him, so he didn’t have to do it. I bet he did the same with Garner, and I bet ARod did the same with her.
      So he’s not really the one who got away,he’s the one who was incapable of having a healthy relationship and pushed her away until she finally left.

    • Myra says:

      I think he did the sabotaging so that she could dump him. He was too cowardly to do even that. The interesting part of that story is how she mended her broken heart with Marc around what ought to have been her wedding day. It’s kind of sad, but also probably a coping mechanism for her not to become depressed. It probably adds layers to the complications of the next relationship. But like Kaiser said, JLo has options. If (when) Ben screws up this time around, she will move on swiftly.

      • a0 says:

        Her marriage to Marc was for sure just a coping mechanism. She said herself it was a “bandaid on the cut” after Ben lol

    • Elixa says:

      My memory is fuzzy, but i remember Vegas with strippers and hookers and her finally calling it quit after a series of bad behavior once that hits the papers. She dodged a bullet. He cheated on her, he cheated on Garner, and he will cheat on her again if they continue. He is not a stable partner.

    • Sunny says:

      I know it’s confusing!

      The article says Ben didn’t want to settle down and she wanted kids.

      Didn’t Ben get married and have Violet shortly thereafter the breakup with JLo?

      I thought he wanted to get married but just not to her.

    • Size Does Matter says:

      Anybody wonder if he sabotaged Bennifer 1.0 because he wanted to be taken more seriously and for people to stop associating him with Gigli and Jenny from the Block?

      I feel like Bennifer 2.0 is a power move for him to prove he’s still got it. Sadly for her I think she really adored him and wants that back.

      • Mel says:

        I think so. From what I vaguely remember it was said that his friends and family thought the relationship was too much of a circus and pushed him to end it. I think he was too much of a coward to pull the plug and decided to act up to the point where she had no choice.

    • Carolnr says:

      The one that got away or the one she couldn’t have?

  3. AnnaC says:

    Is it just me, or does that bottom outfit look like something Jennifer Garner would wear? Only difference is Garner would probably have the shirt cover the abs.

  4. AMJ says:

    No wonder. He’s hardly a catch, but still the only guy on her list one could actually call attractive. ARod, Casper Smart… She usually picks them weird.

  5. KinChicago says:

    Maybe she should see him for what he is- as a compulsive cheater.

    It’s doormat desperate and not at all romantic.

  6. Paperclip says:

    SIB and I’ll SIA: She’s got a bad picker.

  7. facepalm says:

    Oh, this won’t end well lmao. JLo gurl, better put the brakes on your PR churning Bennifer stories every day now or you’ll have an ARod 2.0 on your hands soon. You know Ben will be back to his old ways hitting on anything young with boobs and you’ll be left looking like a clown.

  8. girl_ninja says:

    I’m enjoying this rehash relationship gossip, but she should be glad he got away.

  9. Kate says:

    But is she the love of HIS life?

    • Diana says:

      Not even close. Dude needs to get right with himself before entering any kind of relationship.

    • MF1 says:

      Pretty Ben is the love of Ben’s life.

    • a0 says:

      I’m sure he loved Jen G very much before the wheels came off but there’s no comparison in the heat department between her and JLo. Although it’s easier to have “heat” in a relationship when you’re not caring for 3 small kids

  10. EnormousCoat says:

    He acts the same at nearly 50 as he did then. In case that needs to be translated, it is as follows: WARNING, WARNING. This man does not mature. This man will drag you down. This man is NOT the one who got away, he’s the one who is always getting away with it.
    I mean, it is Page Six so whatever. But my comments about BA stand.

  11. myjobistoprincess says:

    Jennifer has a badpicker no question about it. But she is a good person, that is why a trail of exes would come back to her. All of them probably had issues and did her wrong that is why they’d crawl back. I would not accept them back, but jennifer gives chances – I wouldnt. except for that one guy a long time ago… lol

  12. Robyn says:

    …him?

  13. Dottie says:

    Am I the only one who thinks this whole thing has been created for the tabloids so we keep talking, writing, thinking about JLo & her power over men? I’m just an old cynic, I guess.

    • facepalm says:

      Nah, you’re not. Smelled like a PR stunt from the beginning to show everyone how desirable she is and to bury the talk about ARod cheating on her. Gotta give it to her, this one’s a big “fuck you” to him but methinks she chose the wrong person to do it with because Ben is well… Ben, he’ll never change, and this whole thing is gonna blow up in her face. I mean, just a month ago that influencer outed him for hitting her up on Raya so yeah, just a matter of time until he goes off script. He won’t be able to help himself for long, it’s just the way he is.

    • Jo73c says:

      definitely not the only one!

    • a0 says:

      She has always talked about Ben in a wistful kinda way. This source might not be real but it’s definitely the vibe she’s presented herself

  14. Diana says:

    I feel like I am the only person disappointed in this relationship. She is a grown woman and should know better. It upsets me when I see women who have the world at their feet keep going back to toxic relationships!!!! At what age do we finally learn?

    • Snuffles says:

      I mean, I could sympathize if she wanted to have a brief walk down memory lane with a summer fling post major break up. But her turning her life upside down, dragging her children into it and trying to build a life around something so new and flimsy is just SAD.

      • Diana says:

        It is. I guess they are attracted to each other’s toxicity. He is a known addict, but so is she- she is the poster child for love addiction.

    • Merricat says:

      +1

    • Myra says:

      For me, it’s because she is a grown woman that I don’t feel strongly about her choices. She knows how Ben is, she knows how it will play out and she still chose this. It’s her mistake to make and her life to live. Toxic people are better together, I would think. But tbf I don’t consider JLo as toxic, at least not in the way I consider Ben to be.

      • Theo says:

        Agree. If you are a 52 years old multimillionaire and you have consened to be for a second time the partner of the man who cheated on you, he humiliated you and who has many addictions, it’s stupid. It’s not a true love. An intelligent and strong woman loves and respect herself first of all. Plus she has two young children, who two minutes ago had another stepfather. Crazy!

      • Myra says:

        I’m just here for the Hot Girl Summer shenanigans and nothing else. The steamy bum kisses and untangling bikini straps on a yacht. That’s it.

        I do feel bad whenever the kids are mentioned. It must be confusing for them. Maybe they know how their mom is and are super understanding of her flaws. Who knows what goes on in people’s houses. I personally wouldn’t bring a Ben around my kids.

    • Jules says:

      I agree. On top of this, they both have children from previous marriages, and this headline is in very poor taste. NO ONE thinks of the kids, it’s horrible.

  15. DS9 says:

    I think he’s the one she wished it had worked out with.

    To be honest, I think people underestimate how different the world was back then, expectations, how people viewed Jennifer in particular, and the pairing as a whole. Celebrity rankings were infinitely more rigid. I don’t think Ben’s friends and family ever let him feel comfortable in the relationship, media seemed to have these great expectations of Affleck as a “serious actor” and pairing up with J.Lo, doing music videos, etc wasn’t it.

    That doesn’t excuse his cheating at all but In not sure J.Lo is looking at that as much as what this pairing is in today’s celebrity landscape and how they are on the same level professionally that they weren’t before. She might view his previous antics as youthful insecurity, idk.

    And my impression is that Marc Anthony adores her in an abstract sort of way with some controlling underpinnings, not in an equal, mutually beneficial pairing. She’s an ideal for him, not necessarily an individual.

  16. Driver8 says:

    These two are so bland. I am curious about what happened to the pink diamond engagement ring he gave her. That was the only interesting thing about them.

  17. LORENA says:

    Makes me wonder if that’s why she left Arod, cause she knew Ben was interesting in rekindling. Arod absolutly deserved to be dumped, but would she have broken off their engagement if she didn’t have a jump off? At the very least it gave her the push she needed. I’m all for it tho 😅

  18. India says:

    Jennifer is like a flea jumping from dog to dog. That must be exhausting.

  19. Emily H says:

    Oh, Jen. You are awesome, but this will not end well. I don’t mean this ugly, but Ben is an alcoholic and a gambling addict. He has had periods of sobriety, but always seems to relapse. It signals a life-long struggle and an addiction that he will likely succumb to one day. End stage alcoholism is not pretty, and it tears down your body fast. Relapses get more scary in the end. The physical and mental descent happens so rapidly. My heart hurts for her, because I am sure she thinks she can fix him and heal him with love and understanding. I speak from experience. I hope I am wrong, I truly do. :(

    • Darla says:

      This makes me sad. You’re likely right. I do hope he stays clean though.

    • a0 says:

      I hope Jennifer is already in Al Anon :/ Ben’s been sober for 18 months though, as far as the public knows, and I do kind of believe it because he looks so different physically.

    • Amando says:

      THIS! I still can’t believe how many people are excited about this union. He’s fine for some fun between the sheets, but he’s not someone to have a relationship with. He hates himself and until he works on himself and commits to recovery, he will never be able to truly love anyone else.

  20. Wizzkid says:

    I think Ben was the love of JLo’s life. I also think that while Ben loved JLo, he loved himself more. During their first go around, the tabloids were saying Ben’s friends were making fun of him for that one scene from the Jenny from the Block video where he’s caressing her butt. They thought being with JLo was a step down and was going to ruin his career. Hence, when he destroyed their relationship and forced JLo’s hand to breakup the engagement, he got with Garner real fast. Garner was viewed as wholesome as apple pie (why I don’t know because she’s not that innocent) compared to JLo. Being with Garner was good for his career and image, but I don’t think he was in love with Garner was with him. Ben loved JLo but he is selfish. He loves himself the most.

    Maybe he thinks he made a mistake back then with all the things he did and he still has feelings for JLo. Selfish a**holes still love in their own way. That said, he isn’t a catch but she still loves him.

    • Darla says:

      It’s so true that the deeply selfish actually do love, and sometimes they will find a person they love as much as they could ever love anybody. Then the question becomes, is that enough for the other person.

      • Jayna says:

        That’s a very profound statement, Darla, and so true. And they show intense love in the beginning. It’s what sucks the women in.

  21. Soni says:

    I don’t know. Both JLo and Ben seem exhausting. Neither have any chill.

  22. Lena says:

    She was more in love with him than he was with her, and she realized it. It struck me that in her book she said Marc came into her life 3 days after her wedding was to be. That means it was September 2003. Back then celebrity weddings were a THING, multi-million dollar affairs with pap helicopters over head and hiding in bushes and magazine spreads. And you know JLo’s would be even extra. So it was seismic when they called it off so close to the date. At the time it was said to be ‘’postponed’’ and she gave him 3 more months and when he didn’t set a date she knew Marc was there or she wouldn’t have left (imo.) 17 years later it gets out publicly that AR is insta messaging with some reality girl and Ben,just dumped by his young GF, knows her history of leaving if she’s got somewhere else to go. Good for both hurt egos.

    • Jayna says:

      The last straw for J-LO, who kept hanging on after the canceled wedding, was he didn’t bother to show up to her New Year’s Eve party. She finally threw in the towel. Well, she really had no choice. He was checked out.

      • AnneSurely says:

        If I remember correctly, he was really embarrassed at the media circus. Not that he was the subject of media scrutiny, but that it was trashy, salacious stuff and not fawning, serious praise for the image he had created.

  23. Carolnr says:

    Some of this is definitely a PR stunt! Did you notice the placement of JL’s hands while she was kissing Ben at her sister’s birthday party? It looked like a side- ways ok to the paps to me. Unfortunately, her son interrupted the their kiss & the look on JL’s face went from bliss to actually looking upset! Max is too cute & he seems like he would say whatever comes into his mind!
    There were rumors that back then when Ben was with JL,, the paps didn’t want pics of Ben & even asked him to step aside! ( they only wanted JL) I think Ben totally lost his identity & the media portrayed him as JL’s boy toy! Ben even in an interview admitted to being able to sell magazine covers but not his movies. I notice know how ” the source says Ben pursued her, Ben is a manly man & Ben has matured.
    They both claim incessant media for one of the reasons for their breakup, JL likes to be the center of attention wherever she goes ( that hasn’t changed) Ben once was quoted as saying that he could sell magazine covers, but not his movies. I think Ben will grow tired of that like he did before & realize why they broke up the first time!
    At Ben’s daughter’s graduation, I thought it said that Violet was not present. Ben seems to have a special bond with his children, but especially Violet. I hope that was because they just didn’t get a pic of her or she had another engagement. Those kissing pics went public the day before the graduation…

    • KissMyA**23 says:

      I do think a LOT of it is a PR stunt. I think Ben’s along for the ride for the time being. The way he currently acts around her is quite different from the first go-around. Grant it we don’t have a ton to go on. And that might change soon… but I personally think it will end way quicker than anyone wants (e.g. after the met gala). But who knows.

      I wonder how long it will take to implode this time?

      Side note: as for Violet, I hope she’s ok. She wasn’t pictured with Ben for almost a year previously. I really don’t think she liked Ana (but I have nothing to support that.) Since she’s the oldest, she may just be busy with friends, etc. But it seems weird she wouldn’t have gone to her sister’s graduation.

    • Jayna says:

      The paps did want photos of Ben and Jen together back when. The Bennifer relationship was selling huge amounts of magazines with them on the cover and clicks on websites. It was huge. Even Jennifer Lopez has stated that Ben hated the attention. Of course, he has proven he can be quite thirsty himself for photo-ops as time went on.

      But I agree with you about that making-out photo with the family there. It is just too weird, that look she had when her own child interrupted them at a family dinner. She definitely knew the paps were there and upset the shot was being messed up or upset her lovefest with Ben was being messed up.

  24. NH02 says:

    Can we please stop the narrative that Marc would run back to JLo? He tattood the Statute of Liberty over JLo’s name when he was with his ex wife Shannon De Lima because she “freed” him from that relationship and he compared her to a SISTER when she presented him with the 2016 Latin Grammy Person of the Year award:
    https://youtu.be/5hMtIUmWbqs

    JLo is a mess in love and thinks only of herself. She posted a video of her daughter crying when the ARod breakup rumors started a few months ago and now she is making out with him in front of her kids.

    • Jayna says:

      I know. He is not pining for Jennifer. He really liked Casper. JLO said so and Marc said in an interview he really liked Casper. He and Casper got along well. He is not jealous of men with JLO. He’s too busy chasing after his newest 20-something-year-old. Does he care for Jennifer? Absolutely. They have children together and are both very driven and have worked together regarding projects since their divorce. I doubt he was faithful to Jennifer during their marriage.

  25. Mel says:

    JLo is no one’s victim here. She’s a hot mess, she almost goes out of her way to pick problematic men, immediately moves them in with her kids and gets engaged to them. In Affleck’s case she should have burned some sage around him, wished him well and told him to keep it moving but no, because the second time is ALWAYS the charm.

  26. a0 says:

    Best case scenario: Ben realizes that JLo is out of his league and that he does better in a long-term relationship. There weren’t rumors of cheating with Ana so maybe he’s finally getting his shit together.

    Worst case scenario: JLo moves to LA, involves him in her children’s lives, and then he flakes out again.

  27. Susie says:

    I don’t get the people who think this is a bad look for jlo. I think they are forgetting that it’s jlo and not the normal Jennifer they grew up with in school. The fame and the money make a difference these people are not like us. Jlo loves loves but she loves herself more. In fact affleck would suffer more. Jlo will be in this relationship for as long as it works for her and the second it stops she will find someone else and then leave affleck.
    While I don’t think this will be a forever love I do think this will work out better than Bennifer1.0 cuz affleck doesn’t seem embarrassed this time around. He, his friends and family and the media were all embarrassed that the smart white boy was with a Sexy Latina back then. She was seen as beneath him and so he self sabotaged. This time he seems a bit mature and I bet his family including garner is like whatever makes him happy and keeps him healthy we are fine with. As for the kids I do think people forget these are celeb kids this isn’t their first rodeo with this attention and a lot of their friends are from Hollywood and understand/go thru the same. Especially jlo and affleck who kids have been exposed to the media more than most celeb kids ( I would actually argue that jlo has better protected her kids from the paps than affleck and garner) If jlo or affleck were dating normal people than I would be more worried about that persons kids. I’m not dismissing that celeb kids have to deal with a lot but they are also taught and protected in ways that we will never know or understand I think we project how normal kids would experience this life and forget celeb kids have never been normal and cuz they grow up
    In Hollywood their whole community is abnormal.

  28. JillyBeann says:

    I can so see that they bond on their humble hardworking beginnings. Please adopt me!

  29. Nev says:

    I’m sorry. Her look in the pants and brogues. AMAZING.

  30. eliza james says:

    The one that got drunk, high, cheated, gambled a fortune and then got away.