VOICE OVER: Rebecca Brayton WRITTEN BY: Lindsey Clouse
#30: Courteney Cox & Johnny McDaid
12 Years
How many couples can say they were introduced by Ed Sheeran while partying with Taylor Swift? Cox started dating singer Johnny McDaid shortly after her divorce from David Arquette was finalized in 2013. Just six months later, the two got engaged, but they broke it off about a year after that. However, by spring of 2016 the actor and rockstar were back together again. Although Cox lives in the U.S. and McDaid lives in London, they manage to make the long-distance relationship work with frequent visits and plenty of zoom dates.
#29: Ewan McGregor & Mary Elizabeth Winstead
14 Years
These two actors were both married to other people when they met on the set of the TV show “Fargo.” McGregor played a parole officer and Winstead played the parolee he’s dating. Their fictional relationship must have led to real-life sparks, because the two announced their separation from their respective spouses in May of 2017 and soon began dating each other. They had a son in 2021 and finally tied the knot in 2022. The pair has continued working together over the years, appearing opposite each other in “Birds of Prey” and once again playing a couple in “A Gentleman in Moscow.”
#28: Tig Notaro & Stephanie Allynne
14 Years
Believe it or not, when Notaro and Allynne met on the set of “In a World…”, Allynne had never dated women before and identified as straight. But she couldn’t deny her connection with Notaro. The two bonded over their shared sense of humor and began texting each other for hours at a time. By late 2015, they were married, and had twin sons the following year. It turns out that marriage and parenthood are ripe sources of comedy for Notaro’s standup routine. Like many other couples on this list, the two have continued working together, with Allynne directing Notaro’s latest special.
#27: Chris Evans & Alba Baptista
16 Years
This pair managed to keep their relationship a secret for over a year before going public in November 2022. They got married in an extremely private ceremony in September 2023, in the midst of Evans’ year-long hiatus from acting. We can understand why they’d want to stay out of the public eye. Plenty of internet commentators have been critical of Evans for dating a much younger woman. But it’s not hard to figure out what Captain America sees in Baptista. The multilingual Portuguese actress is a devoted humanitarian and clearly has a fantastic sense of humor.
#26: Kevin Kline & Phoebe Cates
16 Years
Many people might be surprised to learn that these two are a couple, since Cates has mostly stayed out of the public eye since the early 90s. But they’ve actually been married since 1989. Cates and Kline met in 1983 when Cates was auditioning for “The Big Chill.” They began dating two years later, and the rest is history. The two appeared in a couple of films together before Cates stepped away from the spotlight to raise their family. However, in 2001, the pair teamed up on screen again – along with their kids – for the small dramedy “The Anniversary Party.” After almost 40 years together, their love has proven it will stand the test of time.
#25: Jerry Seinfeld & Jessica Seinfeld
17 Years
Although their relationship began with a bit of a scandal, the Seinfelds have managed to make things work for more than a quarter century. When they met in 1998, Jerry was fresh out of another relationship with a much younger woman, whom he’d started dating when she was just eighteen. Jessica, on the other hand, had just gotten married and recently returned from her honeymoon. The two began dating, and Jessica divorced her husband two months later. Despite the scrutiny from the media, the couple has proven that nothing can stand in the way of two people who are truly in love.
#24: Bradley Cooper & Gigi Hadid
20 Years
Hadid must have a thing for older actors who have a thing for younger women. Shortly after her romance with Leonardo DiCaprio, the supermodel was spotted spending time with another man twenty years her senior. She and Cooper were first seen together in October 2023 and apparently have been going strong ever since. Friends say that, despite the two-decade age difference, the pair have a lot in common. Both are parents of young daughters from previous relationships, and the two reportedly have a similar sense of humor. If the relationship turns out to have staying power, can you imagine how gorgeous Cooper and Hadid’s kids would be?
#23: Ice-T & Coco Austin
21 Years
This celeb couple really does make us believe in love. When they met on the set of a music video, Coco fell for Ice’s charm right away. Now, more than twenty years later, they truly look like they’re still smitten with each other. Coco and Ice have been through a lot over the last two decades – ups and downs in their careers, producing and starring in a reality TV show about their lives, and of course, raising a daughter together. Yet through it all, it’s obvious to everyone that Ice still loves Coco.
#22: Leonardo DiCaprio & Vittoria Ceretti
24 Years
We don’t yet know whether this love will have staying power, or whether Leo’s eyes will start wandering when Ceretti gets a bit older. That said, she’s already over 25, the age at which DiCaprio tends to move on from his girlfriends. She might not have been born when “Titanic” was released, but the two seem to find plenty of things to talk about when they’re spotted together in public. The Italian model is already a world traveler with a very successful career. We hope Leo’s not just relying on his fame to keep Ceretti interested.
#21: Jeff Goldblum & Emilie Livingston
30 Years
You might be worried that a 70-year-old man who marries a contortionist 30 years younger than him has bitten off more than he can chew. But to be fair, he’s not just any 70-year-old man. He’s Jeff Goldblum. He and Emilie Livingston met at the gym, where we can imagine the Olympic gymnast caught a lot of people’s eyes. Goldblum had the courage to shoot his shot, and Livingston fell for him. Now, the pair have been married a decade and have two kids together. It’s actually really romantic when you think about it.
#20: Elton John & David Furnish
15 Years
If we learn anything from Elton and David’s love story, it’s that if you’re single, you shouldn’t hesitate to accept an invitation to a dinner party because you might just meet the love of your life. That’s what happened to Furnish when he agreed to be a friend’s plus one to a dinner party at Elton John’s place in London in October of 1993. David and John hit it off immediately and obviously the 15-year age difference didn’t bother either of them, as David returned the next night for a one-on-one meal with the Rocket Man. The couple has basically been together ever since, creating a civil union in 2005 and getting married in 2014 a few months after same-sex marriage was legalized in Great Britain.
#19: Hilarie Burton & Jeffrey Dean Morgan
16 Years
In May of 2009 a soon-to-be 27-year-old Hilarie Burton and a just-turned 43-year-old Jeffrey Dean Morgan were introduced by their mutual friends Jensen Ackles and Danneel Harris. Danneel was Hilarie’s former co-star on “One Tree Hill” and Jensen had worked with Jeffrey on “Supernatural.” Well, as it turns out, sometimes your friends do know what’s best for you. And these two didn’t waste any time consummating their relationship either, as Morgan hinted on Instagram in May of 2021: “Been with her ever since that night. In fact… two kids later… one 11 (do THAT math!)”. They were happy then and they still are now, so a 16-year difference clearly didn’t – and doesn’t – matter to them!
#18: Heidi Klum & Tom Kaulitz
16 Years
As with many of the couples on the list, Klum and Kaulitz hit it off right away. They first met while Klum was in her home country of Germany hosting “Germany's Next Top Model.” Kaulitz, the guitarist for the German rock band Tokio Hotel is, well, also German and that connection turned out to be just one of many things these love birds had in common. As one source told US Weekly, “They fell into an easy rhythm really quickly.” One thing they don’t have in common is their age. When Kaulitz was born in September 1989, Klum had recently turned 16. But as Klum told InStyle, besides when people ask her about the age difference, “I don't really think about it that much otherwise.”
#17: Patrick Stewart & Sunny Ozell
37 Years
It’s true that they have an age gap of well over three decades. But since Sir Patrick Stewart hasn’t aged since the late eighties, they really shouldn’t even qualify for this list. All jokes aside, the pair have a healthy sense of humor about their age difference, and they don’t seem fazed by other people’s opinions. They met while Ozell was waitressing and Stewart was performing in “Macbeth,” and tied the knot in 2013, with Stewart’s longtime friend Ian McKellan officiating. These days, when they’re not working, they spend their free time fostering shelter dogs and looking stunning together on red carpets. Talk about relationship goals.
#16: David Cross & Amber Tamblyn
19 Years
Did you hear the one about the young actress who hung out with the comedian 19 years older than her on a plane and fell in love? While you might think this was a setup to a David Cross comedy sketch, it’s actually how he met his beautiful wife, actress and writer Amber Tamblyn. Cross has said that despite having seen one another around LA, he was “slow to make any moves because of our age difference.” But you also can’t fight true love and Cross has also said that from the moment they met on that plane it was “so obvious” they would eventually be together. And they did eventually start dating, get married, and have a child together… which we assume means that Tobias got over that never-nude thing.
#15: Dennis Quaid & Laura Savoie
39 Years
Unlike most of the people on our list, Savoie isn’t in the entertainment industry. A mutual friend introduced her to Quaid in 2019 when she was a PhD student, and Quaid says it was “love at first sight.” They got married just a year later. According to Quaid, the couple barely even notice the nearly four-decade age difference. Now, she’s a certified public accountant with multiple degrees in finance. Savoie and Quaid might not be able to bond over their jobs, but they do connect over their shared Christian faith, which plays an important role in their relationship.
#14: Dick Van Dyke & Arlene Silver
46 Years
Van Dyke loves to tell the story of how he met his much younger wife. And like Patrick Stewart and Sunny Ozell, Van Dyke and Silver clearly have a sense of humor about the whole age thing. You kind of have to when all four of your kids are considerably younger than your wife. Despite their age difference, the two seem to have a genuinely sweet and wholesome relationship. They were friends for several years before things got romantic, though it’s pretty obvious that Van Dyke was smitten with Silver from the start. He might be old enough to be her grandfather, but they’re both young at heart.
#13: Alec Baldwin & Hilaria Baldwin
26 Years
It sounds like the IMDB summary of a romantic comedy: a soon-to-be 53-year-old man is having dinner with a friend when he sees a beautiful girl. Sure, she is 26 years younger than him, but that doesn’t stop him from walking up to her and telling her “I must know you.” He gives her his number and less than a year and a half later they’re married in New York City. Well, it isn’t a movie, but the man in the story is a movie star. The man was Alec Baldwin, the woman was the soon-to-be Hilaria Baldwin. The couple is still going strong and have added six kids to the mix as well.
#12: Kris Jenner & Corey Gamble
25 Years
It’s a tale as old as time. You’re in Ibiza, you’re having a good time at Kanye West’s party for fashion designer Riccardo Tisci's 40th birthday and you happen to notice the momager-mogul of the Jenner/Kardashian empire. She’s about 25 years your senior, but you get to chatting and a few months later you’re a couple. Come on, who can’t relate to that? Ok, so no one except Corey Gamble can, and while many in her family weren’t too sure about him and the relationship, Jenner was and has remained so. Which is all that matters right?
#11: George Clooney & Amal Clooney
17 Years
George Clooney was one of Hollywood’s great bachelors. That was true until July of 2013 in Lake Como, Italy when he met the brilliant and beautiful Amal Alamuddin. But while there was a pretty immediate attraction on Clooney’s end, the “Ocean’s Eleven” star was a little unsure about how Amal felt towards him, because of the age gap. As he told Howard Stern, [“I couldn’t tell if she liked me because I’m 17 years older than her. So she might have thought I was you know, grandpa.”] Obviously she didn’t, or she really likes grandpas, because in October they reportedly had their first date and in April of 2014, their engagement was confirmed. Well done, grandpa!
#10: Sam Taylor-Johnson & Aaron Taylor-Johnson
23 Years
In 2008, Aaron auditioned for the film “Nowhere Boy.” The film was Samantha’s directorial debut and when Aaron walked in she found the leading man in the film and in her life. And while a 23-year age gap might seem like a big deal to some, Aaron told The Telegraph UK that, “When I met Sam I'd already lived a life far beyond that of most of my contemporaries – I didn't relate to anyone my age.” Now, while the connection was intense, the actor and director kept things very professional during the making of the movie. They still hadn’t been on a date or kissed when the film wrapped, but the moment they were done Aaron told Sam he was going to marry her.
#9: Jason Statham & Rosie Huntington-Whiteley
20 Years
We’d love to tell you how these two met, but we don’t know. Some reports have them meeting at Coachella, while others put it on the set of “Transformers: Dark of the Moon.” We do know that it was 2010, and while the 20 year age gap did raise some eyebrows, Rosie has said that they “have a connection that has nothing to do with age.” For those curious about wedding bells, Rosie has said that she believes in marriage but, “being in a happy relationship is much more important to me.” And while they did get engaged in 2016, they have yet to officially tie the knot. They do have two children together.
#8: Elliott Spencer & Stephen Fry
30 Years
Comedian, actor, and writer Stephen Fry has been a staple of the British comedy scene since the 1980s. And speaking of the 80s, his husband, Elliott Spencer was born in said decade, 1987 to be exact. Which was the same year that Fry turned 30. But, even though Stephen had found lots of professional happiness, personal happiness wasn’t as evident until he met Elliott in 2012. As you may have expected, there were some shocked onlookers given the age gap between these two. But as you also probably expected, Spencer shot back at the haters saying, “I don’t care what people think. Stephen is the love of my life, the light of my life.”
#7: Ben Kingsley & Daniela Lavender
31 Years
From “Gandhi” to a “Sexy Beast,” Ben Kingsley has played many roles over his long and illustrious professional career. And the same is true for his private life, in which he has played the role of husband four times, including his marriage to Daniela Lavender – which began in 2007 when he was 63 and she was 32. While the 31 year age difference is a lot, it isn’t new to Kingsley who, in the 90s dated Kate Townsend, an actress who was 30 years his junior. They dated, but no, she isn’t one of his three ex wives.
#6: Warren Beatty & Annette Bening
21 Years
If you thought George Clooney was one of the great bachelors, let us tell you that his bachelorhood doesn’t hold a candle to one of the all-time most iconic Hollywood bachelors, Warren Beatty. In fact, Carly Simon – who has said that the second verse of her famous song “You’re So Vain” is about Beatty – when talking about having dated the famous actor, followed it up with, “Hasn’t everybody?” And that was very true until he met Annette Bening for lunch to prepare for their co-starring roles in 1991's “Bugsy.” That was it: the 50-something-year-old Beatty had found his perfect someone in the 30-something-year-old Bening – and his bachelor days were over. They were married in 1992.
#5: Harrison Ford & Calista Flockhart
22 Years
Sure, the odds are really low that someone who has never seen the original “Star Wars” movies would end up married to the man who played Han Solo in those films…. But, you know how Han feels about odds! Yes, it's true, Calista Flockhart hadn’t seen the films when they first met and, as she told Jimmy Kimmel, she had no idea what a Millennium Falcon was for quite some time. But that and the 22-year age difference were no match for the true love that started to bloom between these two when they first met at the 2002 Golden Globe awards. According to Calista, she even sometimes forgets how big the age gap between them is, telling Hello magazine, “It doesn't factor into our relationship at all.”
#4: Michael Douglas & Catherine Zeta-Jones
25 Years
Douglas and Zeta-Jones share a love for each other and a birthday. Yup, Michael and Catherine were born on the exact same day, September 25th – just 25 years apart. We don’t know if that amazing coincidence has anything to do with it, but the “Traffic” costars have remained one of the strongest couples in Hollywood since meeting all the way back in 1998. After seeing her in “The Mask of Zorro” Douglas, like pretty much everyone else in the world, wanted to meet Zeta-Jones. But, unlike the rest of us, what Michael Douglas wants he often gets and this was no exception. They ended up meeting thanks to being introduced by a fellow actor while they were both in Europe for a film festival. They were married in 2000.
#3: Rod Stewart & Penny Lancaster
26 Years
One of Stewart’s biggest hits, “Maggie May” was based on his experience of losing his virginity to an older woman. And while his first time was with an older woman, he has spent the years since 1999 with a woman 26 years his junior who he met when she accepted a dare from her mates to request an autograph from the singer. Penny was in her late 20s at the time and was studying photography. The next night, she found herself invited to a show to take pictures of Rod. Stewart got her phone number, but didn’t call for six months – allegedly because it was too soon after the breakup of his last marriage. Penny and Rod eventually tied the knot in 2007.
#2: Sarah Paulson & Holland Taylor
32 Years
Paulson and Taylor started dating in 2015, 10 years after they first met. And no, this wasn’t one of them playing the long game or trying to get out of the friend zone. This was two people meeting at a party and being attracted to each other. As the Marcia Clark actress told the New York Times, Taylor was “probably the most exquisitely beautiful woman” she’d ever seen. But both women were in relationships at the time, so that was that. Cut to 10 years later, they meet again, they’re both single and they start following each other on Twitter. And anyone who thinks older people don’t understand social media should know that it was Taylor – then in her early 70s – who first slid into Paulson’s DMs.
#1: David Foster & Katharine McPhee
35 Years
McPhee might have been runner-up on “American Idol’s” season 5, but she’s the winner of David Foster’s heart. Although, it took a while for them to get there. In fact, the two first met during her run on the show when the 22-year-old performed Whitney Houston’s “I Have Nothing,” a song that Foster wrote. Even though there are over 35 years between them, this meeting led to a great friendship and Foster even played piano at McPhee’s wedding when she married Nick co*kas in 2008. McPhee filed for divorce in 2014 and she and David were spotted getting “cozy” in public in 2017 right around the time that his fourth divorce was being finalized. McPhee and Foster married in 2019 and had their first child together two years later.
Which couple’s story do you think is the most romantic? Let us know in the comments.
