Ben Affleck flooded Jennifer Lopez with emails full of ‘longing’ in February

Ben Affleck pictured picking up his favorite coffee delivery!

Ben Affleck is a writer of love letters. Even though I barely wrote about Ben Affleck and Jennifer Garner, I know that he wrote to her as a way of courting her. I believe some of his other girlfriends have said that too, that he’s a letter-writer and he actually writes some beautiful letters. So… funny story. Shortly after Ben’s breakup with Ana de Armas was official, Ben wrote Jennifer Lopez a series of emails which were reportedly full of romance and longing. She was literally engaged to Alex Rodriguez at the time! But we’ve always known that Jennifer likes to have someone waiting in the wings before she dumps her current man. So that’s exactly what happened – Jennifer and Alex were having problems for several months, Ben wrote her some love letters (emails) and suddenly she was over A-Rod completely and ready for Ben.

Ben Affleck and Jennifer Lopez didn’t just rekindle their romance within the last 2 weeks, instead, it’s been building since February … when he started flooding her with emails while she was filming in the Dominican Republic. Sources with direct knowledge tell TMZ … Ben and J Lo were in very regular contact by email starting in early February when she flew to the Caribbean to begin filming “Shotgun Wedding.” We’re told the tone of the emails wasn’t just friendly … but more loving and longing for Jen.

For instance, after seeing pics of Jennifer in the D.R., he wrote to tell her how beautiful she looked, and how much he wished he could be down there with her. Of course, he was busy at the time in Boston, shooting “The Tender Bar” with George Clooney — and she was still engaged to Alex Rodriguez.

Our sources say the emails also referenced J Lo’s love for Ben’s writing, and included a line about him being able to “own her heart” with his pen. We’re told they continued emailing each other, back and forth, for the duration of J Lo’s shoot … which wrapped in late April.

As far as our sources know, there was no physical contact or rendezvous between them during this time, but the emails do add context to how they seemingly got together so quickly. Remember, they were together in L.A. — very publicly — on the first weekend in May … just 2 weeks after Jen and A-Rod called off their engagement.

Folks in Ben and Jennifer’s world said they had always maintained a friendship since splitting up in 2004. However, as we first told you, they were together again in Montana this past weekend.

[From TMZ]

I’m honestly going to do a timeline so we know where everything stands, and plus it will just help me as a gossip (CB helped me a lot with the Afflarmas timeline):

Fall 2020: Afflarmas seems to be cooling down. There are fewer pap strolls between Ana de Armas and Ben, but they’re still together.

December 2020: Ana de Armas travels to Cuba to spend the holidays with her family. Ben does not travel with her, and they seemingly spend weeks apart.

Mid-January 2021: Ana and Ben are done. The breakup is confirmed quickly and Ben gets his side of things out there. He publicly plays the sad sack.

January 20, 2021: A-Rod attends the Biden inauguration with J.Lo and people joke about how surprised they are that Jen & Alex are still together.

Late January 2021: Jennifer flies to the Dominican Republic to begin filming Shotgun Wedding. Alex does not travel with her, but he will visit her a few times over the next few months.

Early February: Rumors abound about Alex Rodriguez’s possible affair with Madison LeCroy.

February: Photos of Jennifer on the Shotgun Wedding set are widely circulating through the media. Ben Affleck begins writing Jen emails full of longing and love. Jennifer begins to pull together her exit from her current engagement.

Mid-March: The first stories and confirmations of a J-Rod breakup appear. Alex flies to the Dominican Republic to reconcile with her. They issue a joint statement saying that they’re not over but they’re trying to work through some things.

Late March: It becomes clear that Jennifer is totally over Alex and she begins to leak stuff about how she doesn’t want to be with him anymore, and that they’ve been having problems for months.

April 15th: Jen and Alex break up, for real this time. Jen wants us to know that she dumped him. She also wants us to know that she’s completely done with him and she’s moving on and he’s still worked up about it. Alex publicly plays the sad sack.

April 30th: The first reports of Jennifer and Ben spending time together appear. The rest is history!!

Jennifer Lopez and Alex Rodriguez Call it Quits!!! **FILE PHOTOS**

wenn51169

Photos courtesy of Avalon Red, Backgrid and WENN.

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81 Responses to “Ben Affleck flooded Jennifer Lopez with emails full of ‘longing’ in February”

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  1. Lady Luna says:

    Omg someone please get him some help. They need to focus on themselves for a while before jumping into another relationship.

    • Char says:

      Am I the only one who thinks both seem desperate and thristy for the attention?

      • JennyJazzhands says:

        Nope. That’s where I land. This reeks. I can’t even count it as fun gossip.
        As a middle aged person, watching middle aged people make teenaged decisions is…sad

  2. Laalaa says:

    LOVE IT!
    Seriously, this is inspiring! You really NEVER know what life brings. In 2020 it’s Ana, in 2021 JLO!

    He didn’t want the creme brullee. He wanted jello…. :-D

  3. Eleonor says:

    I’m here for all of this!
    I hope they make it until december Bennifer Stories on Instagram! And I hope he will shower her with jewlery…I want to see some jewl pr0n.
    I have to admit: love letters (email) are nice

    • Vesper says:

      I here for this too! It’s just really entertaining and they were so hot as a couple back then. I hope this sticks for them…she can keep him cleaned up. I think he can finally handle being in her light, seeing as his is just as bright and consuming now. They can need each other in a different way, that doesn’t have anything to do with being A-list because they both already are. My only advice is, I hope she keeps her businesses separate for a long while, and just focuses on the relationship as a romantic one only.

      • Sigmund says:

        Ben is way too self-sabotaging for this to last. No one can “keep him clean”. Jennifer Garner tried and failed. And honestly, why would JLO need another project? She keeps going for men who have issues like cheating and, unsurprisingly, it doesn’t work out. She’s better than having to settle for a guy to fix.

        There’s nothing wrong with having a summer fling. It’s fun and they’re hot (though I feel bad for their kids, as they’re probably dealing with a lot of attention from it). But I’d be shocked if it lasted past the summer.

  4. Silver Charm says:

    I mean, I love it gossip-wise but they’re rolling this out in a very transparent old-school PR way which is kind of sad.

    • Ana Maria says:

      exactly! after she leaves/divorces a man, her PR people always put out stories of her being courted by other men and how happy she is

      • smcollins says:

        And it plays perfectly into how “desirable” she is. She doesn’t stay single, not because deep down she’s insecure and can’t be alone, but because men are just clamoring to be with her and waiting patiently for whatever relationship she’s in to end so they can immediately pounce. And in Ben’s case, well, obviously he’s been pining for her all these years. What’s a girl to do? 😉

      • Meg says:

        I think that was brad pitts PR move too ‘hes so desired after his divorce, whos he with now ?’
        But it rang untrue and younger generations especially seem to have a great BS detector

  5. B says:

    Jen Garner must be questioning their marriage now. Was he secretly pining for jlo the whole time they were married?

    • Darla says:

      Well, she’s the only woman he’ll ever have children with, so she has that. And I imagine that’s what ended him and Ana. I admit I was kinda hoping Ana was gonna pull a younger-than-Ben A lister out of her hat…but I guess not. I do admire that she’s kept herself working and going on as if it were nothing and not playing PR games. I think she earns some respect here.

      • Normades says:

        Technically he could have more children but I think he probably told her he didn’t want anymore and she left.

      • Hannah says:

        Men can have children into their 80s. He’s just dumb enough to have more kids to ignore and drag in front of the paps. When his career is waning and he needs them for that of course.

      • a0 says:

        Wasn’t Ana playing PR games by denying rumors that she started herself (posting pictures of the heart necklace)?

    • maddie says:

      I thought so too, but then it was found out that necklace was given to her by a friend. She quickly put the rumors to rest on her ig.

  6. Snuffles says:

    JLo has a very successful, fulfilling life. She’s booked and busy, businesses thriving, loving family, beautiful kids. She’s hot, healthy and fit. Why can’t she be alone for a bit? Is it her ego? Is she terrified of being seen as an old maid? Has she EVER just casually dated?

    • Amy Bee says:

      She has said in the past that she doesn’t like to be alone. That’s why she’s always in a relationship.

      • BothSidesNow says:

        That’s truly sad when you are a full grown woman and you don’t want to be alone. I don’t understand how a woman like JL can’t stand being alone when she seems to have had a stable upbringing, plus raising twin teenagers. Raising twin teenagers should be a handful as it is!!

    • D says:

      She always jumps from one to the other…always. She was still married the first time she got together with Ben. She married that guy right after she ended it with Puffy. Maybe there was a small lag between Marc and that dancer guy, but it wasn’t long. She literally looks exactly the same as she did in 2003, maybe even better! I don’t understand this at all. Love yourself JLo!

    • Becks1 says:

      I think some people are just like that – they don’t like to be alone.

      I also wonder if she was concerned for her image, like she didn’t want it to look like she was alone and heartbroken after A-Rod cheated on her? (which I doubt anyone was thinking, lol.) If I were her I would have done my own “you could have had a bad bitch” tour solo, but I guess this works for her.

    • Laalaa says:

      I think she just lives her life.

    • Hannah says:

      Is she hurting you or something? Just let her do what she wants. Also, why the focus on just her? When has Ben ever been alone for a bit? Never. Plus, he’s a drunkard. If anyone needs to be single and work on their issues, it’s him, not her.

    • Myra says:

      It could be abandonment or self-esteem issues. She might be afraid of being alone. I know someone like that. It’s not necessarily ego (or old maid perception because JLo has been like this since very young), but a need to be wanted and loved. The person I know loved being the centre of attention and being loved by everyone. She was a people-pleaser, which left her exposed to users and abusers.

    • CL says:

      Apparently her life isn’t that fulfilling, seeing her jump from man to man.

  7. Niffy says:

    LOL, these people are instinctively turning into a reality TV show! Super thirsty. Grateful for the Bennifer juice. So goss-y!

  8. minx says:

    Someone pointed out yesterday that she looked happier with Ben than with AR, and I agree.

    • Jules says:

      She looks like she wants to give a backhand bitch slap to Arod where he’s kissing her shoulder lol.

  9. Mtec says:

    I wonder who’s leaking these emails

  10. Abby says:

    LOL, the header photo of Ben holding dunkin’ iced coffees is perfection. :-)

    This story is the gift that keeps on giving.

  11. Amy Bee says:

    I think Ben always regretted breaking up with JLo. If they can find love again, I’m here for it.

    • Lena says:

      He treated her horribly so I’m sure there’s guilt there. It wasn’t just that he fingered strippers during his engagement. If someone called off My wedding 3 days before, I don’t care what the reason, I couldn’t forgive and forget that rejection.

  12. Eleonor says:

    I hope JLo and Ben Affleck pr team will have a raise they are working like crazy.

  13. Diana says:

    Ugh!!! Effing gross! Jennifer- you are a smart, successful, talented, well-loved and well-lived person… how can you fall for this bullshit?! Dude is a mess! Love yourself, Girl!!

    • minx says:

      I don’t think she’s falling for anything. I think she likes what’s happening.Whether they are really getting it on, or just friends, or enjoying the PR, or trying to get back at ARod, she’s all in.

      • Becks1 says:

        Agreed @minx – whatever is happening here (PR stunt, rebound fling, whatever), JLo knows what she’s doing and I imagine is calling the shots.

      • Diana says:

        Lol! I hope you’re right! I might be projecting a bit 😂

  14. Normades says:

    I dunno why but I’m seriously side eying this. It seems like a PR setup to me *shrug*.

  15. Jayna says:

    I’m starting to believe if Ben hadn’t come along she would have stuck it out with A-Rod at least for a while longer. She kept Casper around another few years after his cheating scandal and only dumped him when he wouldn’t attend a Hampton big-wig- party with her and flew to Vegas with his friends for some fight instead. Five years with Casper on and off. I could see the same with A-Rod. BUT along came Ben with his famous wooing emails, and that’s all Jen needed. She could leave and rub A-Rod’s face in the ground with an A-lister and flip the script to the ending of their relationship. No: Poor Jen, cheated on again, can’t keep love. Instead: The great love of her life, Ben Affleck, chased her with his amazing writing skills, and she left cheating A-Rod. She knew what the headlines would be: A-Rod who? Bennifer is back on.

    • B N A fn says:

      The great love of her life broke up her marriage to her second husband and that lasted a quick 3 years and then the engagement was off. Two weeks later she marry Marc Anthony that lasted about four years. Now Ben is back in the picture to break up another relationship with the “girl of his dreams”, let’s see how long this will last. I’m betting not long. Ben is a alcoholic and gambler, he cannot be trusted it’s always the chase for something he does not have until he gets it then the excitement is gone. Feel sorry forty the kids.

      • Jayna says:

        Well, Ben didn’t break up another relationship. A-Rod was cheating on Jennifer. She ignored the first rumblings of it. Then this last D-Lister got a lot of traction on it for her reality show. That was too much for J-Lo. Humiliated again. Still, I believe she might have let him grovel and stay a while longer until it died down and left him down the road with a new jump-off. But Ben came along as it was going down and pursued her, and there was her opening to save face.

        Ben does love pursuing, and it won’t last. I agree with you.

      • B N A fn says:

        I’m not a fan of any of these people but I read gossip so I’ve been reading about her as a person who lived in the Bronx years ago. I believe she encouraged Ben interfering in her life by accepting “letters” from him starting in February while she was with ARod. IMO, she cannot points finger at ARod… she is just as salty. I always read people saying JLo. always has someone waiting in the wings before leaving . This quick turn around appears right.

  16. S808 says:

    From a gossip standpoint, I’m all here for it. I’m hoping they’re just having fun and not taking all of this too seriously.

    • Jayna says:

      Jen always takes a relationship seriously. When has she really been just a casual dater in all of these years?

      • Alexandria says:

        She’s beautiful and Ben loves being the pursuer. So I understand this gossip. I also understand this keeps both of them in the spotlight and they may want to be the next Brangelina.

        But I will never understand if she takes him seriously. I mean why can’t you just enjoy the sex without thinking long term? He’s a proven douche. So I hope her eyes are open.

  17. Size Does Matter says:

    Didn’t he win an Oscar for writing Good Will Hunting? I bet those emails are pretty amazing. That said, I wonder if ARod put this rumor out there.

    • (The OG) Jan90067 says:

      He did, but all the talk was that Matt Damon wrote 90% of it and Ben was laying on the couch getting high and drinking, or passed out most of the time.

      • Kebbie says:

        Surely nobody believes that narrative anymore though, right? Ben has done a lot more writing (and with greater critical success) than Matt. I think Ben is definitely the superior talent when it comes to writing, producing, and directing.

      • teecee says:

        I’m not sure that’s true? We haven’t seen Matt pursue those fields yet, probably because he was considered the better, more well-respected actor of the two (by far.) In fact, before his awful treatment of Effie Brown became known, Matt was widely considered an “unproblematic fave.”

        I actually bet they’re on par, writing and directing-wise. Meaning: aggressively medium-talented, but hyped up because they make straight white men movies. (aka the Clint Eastwood effect)

  18. whateveryousay says:

    The fact that A-Rod is salty about this has been making me laugh. Keep it up Jennifer! And honestly, I am assuming she and Ben are just having hot sex and that’s it. At least though she’s had her kids and that seemed to be a deal breaker between Ben and Ana. And come on. I want them to get to the Dark Water red carpet at least (Ben and JLo) cause JLo will out stun queen Ana. LOL

    • Jayna says:

      I honestly love Ana. I think she’s so pretty. I believe Casey Affleck, that she’s all the things he said she is. I would see her in interviews, and she’s a very affectionate person and seems really lovely. She’s extremely talented and is just hitting her stride with all of these movies coming out. Ben’s kids really seemed to like her. Dating a guy with three kids is not easy.
      She deserves better than Ben. But for once I think Ben was right. He has an alcohol problem he deals with. He has three children who need his focus on his off time, and he has been doing a much better job of that. At his age and his children’s ages to bring another baby into his life before he has had many years of sobriety under him and until he has been in a long-term stable relationship would be irresponsible. So that’s the one time he’s made a very mature decision.

      • Hannah says:

        The way Casey talked about her… he wishes he met her first. I know Ben misses her and thinks about her at night. I would!

  19. Beech says:

    Looking for the next fix and the rush that comes with the fix. Addicts. Not for them the day to day life with a partner.

  20. Scorpion says:

    Good grief, the PR stunt Queens are at it again. They both give off such a desperado vibe

  21. Lizzie says:

    This is probably just me but flooding with emails is the biggest turn off. I would end it right there.

  22. Hannah says:

    Love letters, smh. He doesn’t look like he can read or write. He’s the type to send a gushy letter and a huge, showy flower arrangement while banging others on the side. Actions speak louder than words… he’s nothing but talk.

  23. LaUnicaAngelina says:

    Keep it coming! I appreciate the timeline too.

  24. Hazel says:

    Really? He was writing those while he had a life sized Ana cardboard? Lmao this story

  25. Nicole says:

    I put this in an email to someone and I stand by it:
    Can we just admit that Ben has a type or he was never really over OG Jennifer? He really has a type. He appears to “get serious” with petite brunettes. Anna was just a younger version of JLO. He kind of rebounded from JLO and got with Jen Garner. Lindsay Shookus was an anomaly. Isn’t the gossip that they were each other’s side pieces when they were married? Regardless, I kind of wonder how much racism played into his decision getting with an “All American” sweetheart versus, JLO who had roots in R&B and Hip Hop.

    Arm chair therapist here (Forgive me for being cynical): Let’s consider the man he was then. He was actively drinking/using and I’m guessing just a tad insecure about what people back home would say. Even though they were both successful in their own right; in her case there is an intersection of race and class.

    By now he’s had time to get with the “good girl” and have produced white children. She has produced Puerto Rican children. I really don’t think he ever really got over JLO. IMO Jen Garner was too type A for him. If she isn’t already, Jen Garner needs to go to Al-Anon meetings to navigate co-parenting with Ben. I think OG Bennifer are just dysfunctional enough to work, and I really to think they are both each other’s “on that got away”.

    I don’t really have a dog in this fight. As someone who was raised in alcoholism, I just wish them both serenity. He’s an alcoholic addict and she’s a love addict. Hopefully they get a level of dysfunction that works for them both.

  26. Lala11_7 says:

    I NEVA understood the theory of needing to be alone after ending a relationship…relationships ARE CRAPSHOOT…PERIOD…I’ve known folks who did it both ways…and sometimes it works and sometimes it don’t…both ways…it just depends on the people involved….

    • Shazze says:

      We all have issues, and if you don’t address them, you’ll keep picking people who are bad for you – or in this case, re-picking – arghh!

    • Darla says:

      Yay! Finally someone who sees things my way. I am with you 100% Lala.

  27. NotSoSocialButterfly says:

    Sure, Jan.

  28. Liz version 700 says:

    Please Jen do not stop briefing People. If you get a crank in your neck from all of the phone calls I have the name of a great massage therapist. This is magnificent. I wonder if Jen Garner is cursing while marching around in her crocks waiting for the implosion lol

  29. Sharon Adams says:

    Him again? Recycling the bad picks from the past? Hope it’s just a pick me up

  30. lucy2 says:

    Of course he did. He did it back when they first got together too, showered her with praise and compliments, and she ditched husband #2 for him. IMO they’re both a bit ridiculous and this will likely end in similar fashion again, but whatever.
    The only people I feel for here are the kids, who have dealt with their parents divorcing, their dad remarrying and divorcing, their mom with that Casper guy for a long time, then ARod for a long time, and their families seemed pretty blended, and now that’s done too.

  31. Susan says:

    I feel like both of them share a love of the rush of new love. It is intoxicating I will give them that. Or the rush of the *idea* of romantic love. A dramatic reunion. The concept of soul mates. The Notebook moment, if you will. Problem is, real life is not that. Real life is leftovers and sweatpants and living together and a little boring. I think that is why they connect…and why ultimately this will fail.

    But it is the greatest gossip gift we’ve been given in quite some time!

  32. Amelie says:

    Lol I love how we are still trying to make Afflarmas a thing. The world at large adopted BenAna as their moniker and I can’t see how that can be superseded, sorry! Also part of the timeline needs to be the very public throwing out of Ana de Armas’s cardboard cutout hahaha. Casey Affleck denied it was him, so it was very clearly Ben who did that.

  33. gilda says:

    In terrifying news, he looks a lot like Don Jr in that photo when I’m not wearing my glasses. I haven’t even read the article yet but I’d like to reiterate: J.LO, you’re in danger girl RUN.

  34. Justwastingtime says:

    That pic is just .. so sad sack.. which is how I think of him

  35. Justwastingtime says:

    That pic is just so sad sack..Lost is not cute at 50. Maybe he gets some of his hotness back but JLO has always been both hot and functional. She can do so so so much better.

  36. Rise & Shine says:

    Haha, yeah a big I don’t know on this one. I mean come on, I am a romantic to the heart but a little skeptical on this one. Moving pretty fast considering they have kids and past marriages etc. I mean, yeah move on but maybe take a minute. please? Oh well, guess it’s either true love or pure PR, maybe a little of both. Guess time will tell :-)

  37. Fernanda says:

    Did any of you fellow celebitchies do something like this? Meaning, hooking up with an ex after so many years and after so much drama? I just don’t think this could end up well. Someone will get hurt. Bottomline, can you just have a sexual relationship with someone you had very strong feelings about?