Ben Affleck and Gwyneth Paltrow's Love Story From Start to Split - THE OWNER PRESS

Ben Affleck and Gwyneth Paltrow Were a Perfect Couple on Paper: Romance Rewind — Gwyneth Paltrow and Ben Affleck in 1998 Stephane Cardinale/Sygma by way of Getty Photos

Since each of them now have a string of high-profile exes behind them, the three yr on-off relationship between Ben Affleck and Gwyneth Paltrow on the tail finish of the twentieth century has been overshadowed by the numerous romantic dramas of their lives since. However, over time, all types of fascinating particulars have emerged concerning the cute however in the end ill-fated romance between two of Hollywood’s most intriguing characters…

The way it Started

Simply weeks aside in age and each a part of the identical younger, proficient, late ‘90s Hollywood set, the pair had been each 25 after they first met at a Miramax dinner in 1997 (and never on the premiere of Affleck’s breakthrough film Good Will Looking later that yr, as has usually been reported.)

On the time, Paltrow — then greatest identified for her roles in Seven and Emma — was freshly single and able to mingle after calling off her engagement to Brad Pitt a number of months earlier, whereas Affleck was newly well-known and had lately break up from his summer season camp sweetheart and girlfriend of seven years, Cheyenne Rothman (then an aspiring director herself, now a full-time mother who prefers being out of the highlight.)

Quickly, Paltrow and Affleck had been happening double dates with one other iconic however short-lived ‘90s couple, Winona Ryder and Matt Damon, and indulging in crimson carpet PDAs. Two beautiful, proficient, clever stars whose film careers had been going stratospheric on the similar time — what might probably go mistaken?

How Lengthy it Lasted

Whereas on paper, these two had been an amazing match, it appears they weren’t fairly on the similar life stage mentally, with Paltrow on the lookout for one thing a bit extra settled than Affleck might supply on the time, as he revelled in his new VIP standing on the wild Hollywood social gathering scene.

Nonetheless, they had been collectively for nearly three years in whole, however it was an on/off scenario that ultimately fizzled into a robust friendship after they lastly break up for good in 2000.

Their relationship was a really busy one, with the pair co-starring in two motion pictures collectively — 1998’s big hit Shakespeare In Love (sure, the one which Paltrow would go on to win the Finest Actress Oscar for in 1999) and the extra low-key romantic drama, Bounce (they had been in additional of an “off” part whereas capturing it, although, and by the point it was launched in 2000, that they had break up correctly.)

The way it Ended

By the point Bounce got here out, they had been over, after realizing they didn’t need fairly the identical issues. “I can inform you unequivocally that Gwyneth and I will not be going out,” Affleck informed Leisure Weekly in 2000 when requested about paparazzi photographs of him hugging Paltrow in Paris. “We’re not a pair. We’re not an merchandise. I do love her very a lot and I care about her enormously, as that image signifies. However I hug lots of people this fashion. Whether or not or not individuals consider that’s as much as them.”

(It’s official, Affleck is a hugger — we noticed the identical factor once more lately when he was hanging out with certainly one of his different very high-profile exes, former spouse Jennifer Garner, at their son Samuel’s paintball party in March 2025.)

Paltrow confirmed the break up on the time, too. “If we’re in the identical metropolis, we exit,” she informed Leisure Weekly. ”We’re shut. Generally once I’m in L.A., I keep in his home. Nevertheless it’s not what individuals assume it’s. We’re not collectively. I swear on my life. We’re not. It’s actually artwork imitating life, solely with out the glad ending in our case. However we’ve one other sort of glad ending, which is that we’ve a friendship. I like his household, much more than I like him. In order that’s a great factor.”

Even throughout the relationship there have been indicators that they weren’t fairly on the identical web page — however they had been at the very least humorous about it. After they appeared on Good Morning America collectively in 1999 whereas relationship, Affleck mentioned that Paltrow’s ideally suited man could be somebody like her dad, and Paltrow hit again that Affleck’s excellent lady could be “any kind of stripper at Scores, anybody that serves chilly beer in a bikini.” After all, everyone knows that Paltrow is extra the kind to serve kombucha in crisp white denim.

Regardless of their variations, they admirably received by way of the break-up in good spirits too. Throughout a Saturday Evening Reside look to advertise Bounce, Affleck popped up throughout a scripted skit with Paltrow. “We simply broke up a month in the past,” he reminded her. “Didn’t you examine it? It was in all of the papers!”

What They Stated About Every Different

Whereas they had been collectively, Paltrow was overtly gushing about her man. “He’s probably the most clever man I’ve met underneath 45,” she informed the Los Angeles Occasions in 1999. “He’s an excellent actor. He has an enormous vary and impeccable timing and actual depth. I believe it’s nice that it’s popping out slowly, little by little.”

In 2000, across the time they lastly break up, she was additionally extraordinarily complimentary about her on/off love in an interview with the New York Occasions. “Ben is affable and charming and individuals are kind of drawn to him,” she mentioned. “He’s disarmingly fast, fiercely clever and, in some methods, an underachiever. Ben had a troublesome childhood, however not a nightmarish one. He loves each his dad and mom dearly. Although Ben had virtually excellent SAT scores in highschool, his grades different wildly relying on his attendance and degree of curiosity. There’s an enormous chasm between the general public and the non-public Bens. In quiet moments, Jocular Ben transforms into Contemplative Ben. He’s not weak straight away; it takes ages to get to that a part of him. I like him in all his incarnations.”

It wasn’t simply Paltrow doing all of the speaking — whereas Affleck wasn’t fairly as effusive (who’s?!), he usually praised Paltrow for serving to him professionally. “One of many issues that Gwyneth taught me is to keep up a degree of labor the place fascinating individuals that you simply like wish to work with you,” he mentioned in the identical interview, to advertise Shakespeare In Love. “And also you do this by doing stuff you assume are fascinating, not by taking part in into some expectation.”

What They Say Now

Because the break up, the pair have been probed about their relationship every now and then and each have been glad to speak about it, with their emotions of friendship seemingly getting hotter and hotter over time as they moved on with new companions (actor Luke Wilson was Paltrow’s subsequent, comparatively temporary, relationship. She then married Chris Martin in 2003 and had two kids collectively — daughter Apple, born in 2004 and son Moses, born in 2006 — earlier than “consciously uncoupling” in 2014 and happening to marry present husband Brad Falchuk in 2018. Affleck, in the meantime, was with Jennifer Lopez from 2002 to 2004, earlier than they known as off their engagement, after which spent a decade married to Jennifer Garner and had three kids — Violet, Fin and Samuel — earlier than their break up in 2015. He and Lopez then shocked the world by getting again collectively in 2021, however divorced after two years of marriage. He’s at present single.)

In 2000, not lengthy after their break up, Paltrow talked about how she usually tried to push Affleck to tackle harder roles. “I’ve all the time had this ongoing dialogue with Ben about doing stuff that required extra of him,” she informed Leisure Weekly because the pair promoted Bounce. “After I see one thing like Armageddon and see him simply not connecting, I get kind of like, ‘Yeah, you’re charming… however it’s not what you’re able to.”

She added: “We didn’t have a type of horrible acrimonious break-ups. The nice factor is that we maintained this friendship. I’ve a kind of brotherly feeling in the direction of him. I need him to do nicely and develop up and be a contented particular person and a completely realised man and be ok with himself, so once I learn the script I believed, ‘Ben has to do that movie. It will be actually good for him to have one thing the place he has to actually sink his enamel in and focus and increase.’ I imply, everybody thought, ‘Don’t do that. You’re making an actual mistake. It’s going to be a drama.’ My father was like, ‘Oh, God!’ I don’t assume he really vocalised something however I noticed that look: ‘This can be a mistake.’ Nevertheless it couldn’t have been higher. We’re so keen on one another and we’ve such a pleasant rapport between us. It wasn’t troublesome in any respect. Folks simply cope with issues in numerous methods.”

In 2002, a few years on from the break up and after Affleck had acquired therapy for alcoholism and was first rumored to be relationship his future ex-wife Lopez, he talked to the Day by day Mirror about how his lack of maturity had led to the break up. “Gwyneth is far more advanced spiritually than I’m,” he mentioned, hinting on the Goop-ification that might comply with. “She does yoga and meditates, and I simply don’t. She is far nearer to internal peace and has a way of calm, whereas I’m far more frantic and I should be energetic. I’ve a really troublesome time sitting nonetheless. We’re very totally different in that respect, however she continues to be certainly one of my closest pals.”

In a 2003 interview with Diane Sawyer, Paltrow was a bit extra unfavorable about Affleck. “Ben makes life robust for himself,” she mentioned. “He’s received a number of complication, and you recognize, he actually is a superb man. So I hope he types himself out.”

Affleck responded in 2004 by way of Rolling Stone, saying “She’s in all probability proper about that. I belief her opinion about most issues. Not all, however most. I believe I in all probability do get in my very own approach.”

In a 2015 interview with Howard Stern, Paltrow was extra reflective and analytical concerning the relationship. “He was not in a great place in his life to have a girlfriend,” she mentioned. “It’s fascinating, I believe there’s sure boyfriends the place you are attempting to work stuff out, proper? Like, you’re attempting to heal sure stuff out of your childhood and he was very a lot a lesson in that approach.”

She added that her dad and mom had been huge followers of Affleck, however understood why they break up. “I believe [they] appreciated that he’s tremendous clever, and actually, actually proficient,” she mentioned. “And he’s humorous. They cherished him however they had been okay with us not being a pair. I like him. I’m pals with him nonetheless.”

On the time, Affleck was married to Garner, and Paltrow mentioned she was glad for them. “Not solely is she stunning, she’s so heat, and he or she cooks, and is so into her youngsters,” she mentioned. “She’s actually nice and he or she’s hilarious. I had a women’ dinner earlier than the summer season and he or she came visiting. She’s my neighbor. I actually like her loads.”

Since then, Paltrow and Affleck have all the time talked fondly about one another — in some circumstances, very fondly, when, on the Call Her Daddy podcast in 2023, she was requested to check him sexually along with her different most A-list of exes, Pitt.

“Brad was just like the kind of main chemistry, love of your life, sort of, on the time after which Ben was, like, technically wonderful,” she mentioned. “I can’t consider my daughter is listening to this!” (Certain sufficient, Apple was within the studio too, with footage later shared of {the teenager} trying shocked along with her fingers over her ears!)

Paltrow added that Affleck was “a great kisser” after which referenced his temporary marriage to Lopez which was in full swing on the time. “God bless J.Lo and every part she is getting over there!” she mentioned with amusing.

She added that Affleck was the funniest of her two huge Hollywood exes (the opposite being Pitt, in fact), but additionally the extra argumentative.

Key Relationship Takeaways

These two had been excellent friends, however not so excellent as a pair. However, regardless of Affleck’s obvious lack of maturity when it got here to their relationship, they managed to cope with the breakup with the thoughtfulness and sophistication they’re each identified for — which is why they’ll now take pleasure in a stable friendship at 52 (however whether or not that makes Affleck probably the most clever man Paltrow has met over the age of 45 stays a thriller!)

Their friendship is unquestionably excellent news contemplating they only can’t appear to flee one another: whereas they’re now not starring in the identical Hollywood motion pictures collectively, now their youngsters are rubbing shoulders as an alternative: Affleck’s daughter Violet and Paltrow’s stepson Brody are each at present of their freshman yr at Yale.

Whereas Paltrow appears very settled with Falchuk, Affleck is, as soon as once more, single — however, understanding Paltrow, she’ll have a protracted record of beautiful pals lined up for him. Properly, it will be a disgrace for these “technically wonderful” bed room abilities to go to waste, proper?

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