Inside Gwyneth Paltrow's Romantic History: The Reality and the Rumors

Now that she's reportedly engaged to marry producer Brad Falchuk, we remember the important leading men in Gwyneth's life—and the ones just lucky enough to be mistaken for suitors

By Natalie Finn Nov 25, 2017 1:00 PMTags

Gwyneth Paltrow made headlines this summer when she self-deprecatingly said that she's "f--ked up so many relationships, so many."

Accountability is always refreshing but, really, the woman who helped usher the term "conscious uncoupling" into the mainstream shouldn't be so hard on herself. Two people who are meant to be, or who are at least ready to commit for the long haul and see what happens, are not so easily wrested apart. Which isn't to say one or the other can't screw it up, but there are countless reasons as to why that relationship was not the right one but this one is. It takes two to tango, and two to break hold.

Brad Falchuk is certainly proof that Paltrow isn't as bad at the coupling part as she might claim. The prolific TV producer and the Oscar-winning Goop goddess are reportedly engaged after more than three years of dating, part of which they spent avoiding any splashy signs of togetherness before finally feeling comfortable going out as official significant others.

"I'm actually a pretty good friend, and a good sister and daughter and mother, but I'm at my potentially most vulnerable and f--ked up in the romantic slice of the pie," Paltrow mused on the podcast Girlboss Radio in August. "So it's taken me a lot of work to get to the place where I have a good romantic relationship."

It's unclear as to whether she's considered herself a work in progress for decades or if she did most of her soul-searching more recently, after she and Chris Martin divorced. But if you've paid attention at all to her latest wellness endeavors, you know that the past nine years, since Goop launched, have been extraordinarily transformative for Paltrow—and if part of that led to a new lease on her capabilities as a partner, then that's great.

Meanwhile, with time comes maturity and hindsight, and hopefully the opportunity to appreciate one's journey for what it is—the necessary path that brought you to where you're supposed to be. Here are the gentlemen who've played leading roles in her life along the way, as well as the bit players who got close enough to be mistaken for potential leading men:

Robert Sean Leonard

Young Hollywood in the '90s, right? These two dated in 1994 and kept a very low profile. Almost no proof exists of their romance aside from myriad vague, past-tense references to dating. But the Dead Poets Society star (who incidentally had a small role in the 1990 drama Mr. & Mrs. Bridge, which also starred Paltrow's mom, Blythe Danner) has at least acknowledged that it happened.

"It was the funniest breakup I've ever had," he recalled to the New York Post in 1998. "We were in her apartment, figured we shouldn't see each other anymore, and within five minutes she was saying, 'You know who you'd like? I have this friend'... Gwyneth's a bit of a yenta, but she's a great, great friend." 

Leonard randomly referenced his ex in a 2013 interview with the U.K.'s Metro, when he was about to star in To Kill a Mockingbird in London. Talking about the pros and cons of fame, he said, "I remember watching Gwyneth Paltrow deliver her Oscar acceptance speech in floods of tears. My God, how open. The poor girl was just so intimate with these unnamed millions of people. I couldn't do that. I just feel like a squirrel at a fox hunt in those things: so awkward and uncomfortable."

Donovan Leitch

Gwyneth's reputation for remaining on good terms with her exes would continue.

It was a real blast from the past when Leitch shared a smooch with Paltrow, whom he dated 20 years prior, when they ran into each other at a Dodgers game in 2014...six days after she and Chris Martin announced their separation, thereby prompting the "need" for an explanation.

"We were sitting in the owner's box in front of 30,000 people with her two children right next to us," he told the Daily Mail. "That isn't exactly the setting for a secret liaison."

Leitch said, "Gwyneth and I have always been close...I consider her to be one of my closest friends. We have tons of great friends in common."

Brad Pitt

The one that got away. For both, perhaps?

"I f--ked that up, Brad," Paltrow said on the Girlboss Radio podcast when host Sophia Amoruso mentioned Gwyneth's great love of the mid-'to-late-90s, whom she met in 1994 on the set of the thriller Se7en, playing his ill-fated wife.

When he won a Golden Globe for 12 Monkeys in 1996, Pitt's final thank you was reserved for "especially the love o' my life, my angel, Gwyneth Paltrow." They got engaged, they even got matching haircuts, but then they broke up in June 1997.

Paltrow has been relentless in blaming herself for the demise of their relationship, telling Diane Sawyer in 2003, "I'm so lucky that I spent time with Brad, somebody who was such a good person! Especially when I was, like, such a mess." Admittedly the relentless media attention—which peaked when long-lens nude photos of the couple taken while they were vacationing in the Caribbean ended up online—really got to her then, understandably so. 

"My kind of internal stuff really tripped up that whole relationship," Paltrow said. "And I felt really responsible, and also like I was the architect of my own misery...I just made a big mess out of it.''

The actress told Howard Stern in 2015 that her beloved father, Bruce Paltrow, who died in 2002, "adored him like a son." But "I was such a kid, I was 22 when we met. It's taken me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old...I wasn't ready, and he was too good for me."

Only recently did Paltrow tell the New York Times that she too was subject to unwanted advances from alleged serial predator Harvey Weinstein roughly 20 years ago, when she was dating Pitt—and that Pitt confronted Weinstein at an event afterward, warning the producer that something like that had best never happen again. So there was more going on at the time for Paltrow to process than anyone publicly knew about for decades.

By the time of the Sawyer sit-down, Pitt was married to Jennifer Aniston. "We're able to sort of see each other and smile and wish each other well," Paltrow said.

Jason Blum

Paltrow reportedly dated Blum, a producer and former Miramax exec, shortly after she and Pitt split up in June 1997—but in hindsight that might have just been a business-bred friendship since Miramax produced Emma and Shakespeare in Love.

When they were spotted seemingly arriving together at an event in 2001, a source told the New York Daily News that they were "just old friends. They were catching up."

In it's-a-small-world news, Blum (whose Blumhouse produced the Paranormal Activity franchise, Whiplash and current potential Oscar contender Get Out) was a producer on HBO's The Normal Heart, which was directed by Brad Falchuk's longtime creative partner Ryan Murphy.

Ben Affleck

If Brad was too good, Ben Affleck wasn't good enough—yet.

The actor, a wunderkind Oscar winner for co-writing Good Will Hunting with buddy Matt Damon, met Paltrow at a Weinstein-hosted dinner in 1997 before they both appeared in 1998's Shakespeare in Love. They had great chemistry, but by the time Paltrow was vacuuming up awards en route to winning her Oscar in 1999, she and Affleck had dwindled to friends status. (Dad wasn't too disappointed by this breakup.) They would then rekindle briefly in late 1999 when they co-starred in Bounce, and end up the kind of friends who stay at each other's house on occasion.

But Paltrow admitted later that she never expected her rebound romance to last. During an interview on Good Morning America, Ben said that Gwyneth's perfect man would probably be someone like her father, while she said that Ben's ideal lady was "any sort of stripper at Scores. Anyone that serves cold beer in a bikini."

"Ben makes life tough for himself," Paltrow reflected to Diane Sawyer in 2003. "He's got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out." She said, "I just think we have a very different sort of value system." Also in 2003, Another Mag reported that Paltrow referred, at an event, to "a drawn-out and tortured relationship with a complete knucklehead"—a comment widely perceived as being aimed at Affleck.

The fellow Brentwood residents eventually became friendly friends again, and Paltrow has also enjoyed socializing with Affleck's now ex-wife, Jennifer Garner. "He's super intelligent and really, really talented and he's funny," she told Stern in 2015. "But he wasn't in a good place in his life to have a girlfriend [when they dated]." As for her stripper comment 17 years prior, she laughed, "Well, that was true at the time!"

Scott Speedman

Paltrow was briefly linked to her Duets co-star—who was cast as a replacement for Brad Pitt in the 2000 ensemble drama, which was directed by Bruce Paltrow and featured Gwyneth's cover of "Cruisin'" with Huey Lewis. "It was a good group of people," Speedman told The Daily Beast in 2012. "If I had to sing in that movie, I wouldn't have gotten it."

Chris Heinz

In November 2000, after she and Affleck ended things for good, the New York Post reported a sighting of Paltrow "arm-in-arm" with the son of Teresa Heinz Kerry (as well as stepson of John Kerry and heir to the ketchup fortune) at the PaceWildenstein Gallery's 40th anniversary party, after they had been spotted together out in Manhattan.

Gwyneth was calling Chris, who supposedly took her to London for their first date, "a breath of fresh air" after all those Hollywood types, sources told the paper.

Luke Wilson

Unlike Margot and Richie Tenenbaum, Luke and Gywneth didn't have to keep their feelings confined to a tent in the attic. 

The actors dated for about a year after they connected while making The Royal Tenenbaums, a seemingly drama-free affair.

In 2001, in an interview published while she was rumored to be dating Wilson, Paltrow told Harper's Bazaar about her ideal man: "He's tall and thin, but muscular, to start with the superficial. A gentleman. Someone who's well educated, funny, witty, artistic, and has a lot of integrity. He doesn't have to grab all the attention in the room. A good kisser."

Summing up her general enjoyment of the opposite sex, she said, "I love men, even though they're lyin', cheatin' scumbags. I'm a very sexual person. I'm lucky if I get past six weeks. The make-or-break is six weeks."

James Purefoy

In 2002, the Shakespeare in Love star got dinged in the U.K. tabloids when she told a local magazine that she had trouble getting dates in England. (Which is ironic, considering.)

"British people don't seem to ask each other out on dates. I did get asked out a couple of times on my last trip to London—and I went out on both," she told Now. "They were very charming. I only go for the toffs. If someone asks you out, they are really going out on a limb whereas in America, it happens all the time. Someone will come up to you and ask you for dinner and you'll say, 'Sure.' It's no big deal and no weight should be attached to it. It's only dinner for God's sake."

One of those brave Brits was James Purefoy, who put his dating derring-do on display after they met while Gwyneth was in town starring in the West End production of Proof. "She's a lovely girl," the Rome star later said of Paltrow in an interview with Harrods Man in 2014. Alas, he claimed, after they were photographed together in his car, his insurance company called to say they were raising his rate due to the added fame in his passenger seat. 

But maybe Purefoy was just being cheeky.

Bryan Adams

In August 2002, with the nation still reeling from her comment, London's Evening Standard pegged the Canadian singer as another of the intrepid sorts who dared to ask Gwyneth out. They were spotted together at the members-only Wellington club in Knightsbridge, after which they were photographed with Paltrow on the back of Adams' Piaggio Zip moped.

Chris Martin

Otherwise known as the British guy who really went for it.

Still mired in depression after her father's death, Paltrow reluctantly went to a Coldplay concert with some friends—and ended up hitting it off with the band's frontman.

They married in 2003 and lived primarily in London, while maintaining homes in New York and L.A. They welcomed daughter Apple in 2004 and son Moses in 2006. Theirs was a red-carpet-eschewing, intensely private marriage, with Martin explaining Howard Stern in a 2011 interview that red carpets were for "selling," and they weren't selling anything. Paltrow talked here and there over the years about marital difficulties, telling Elle in 2011, "We go through periods that aren't all rosy. I always say, life is long and you never know what's going to happen."

What happened was, they separated in 2013, almost a full year before they announced their split via Goop newsletter while riding out the headlines on a family vacation in the Bahamas. At first, post-split, it seemed as though they were spotted together more than ever as they continued to amiably co-parent. Paltrow has candidly admitted, however, that getting to that new-normal place was hardly an overnight process.

"It's also almost about having to press the 'override' button whenever you feel angry or jealous or whatever, broken-hearted," Paltrow told Red in 2016. "You have to press the button—I'm going back to the baseline of 'I love this person, he's the father of my children, he's a wonderful man. I'm just going to put my s--t aside for right now.'"

Brad Falchuk

And then she met Falchuk when she guest-starred on Glee, which he co-created (along with Nip/TuckScream Queens and the American Horror Story franchise) with Ryan Murphy.

"My date and I #screamqueens," Falchuk captured a pic of the two when they became Instagram official in September 2015.

Two years later, all pretenses were off. On Paltrow's birthday in September 2017, he wrote, "This is the most beautiful woman of all time and today is her birthday. We are all so lucky that she came into the world (but no one is luckier than me). Happy Birthday, Love. PS - this is pretty much the most #Gwyneth pic I could find - it has pizza, red wine, her phone and that f--king perfect smile."

For Halloween, Paltrow and Falchuk channeled the head-in-a-box shocker from Se7en, effectively bringing Gwyneth's romantic journey full circle. 

As news of their engagement broke this week, a source told Entertainment Tonight he had given her a ring "a long time ago," but only recently had she been wearing it where people might notice (and subsequently make a really huge deal about it).

"They both knew it would happen, but it wasn't a big thing to them because they were both in long marriages before. There wasn't a rush," another insider told Us Weekly, which first reported the news.

Gwyneth and Brad. Both divorced parents of two. Both independently successful. Both agreeing they're better together.

"I've had an extraordinary life, where things have happened in a huge way—huge success, huge joy, huge pain, huge loss. And the reason I feel happy today is because I've milked the f--k out of every opportunity," Paltrow told The Edit this summer. "I haven't made one mistake that I haven't used as a stepping stone to get somewhere else. I'm ruthless when it comes to using the hard things."