Following his iconic marriage to Demi Moore, which led to three daughters, followed by a short-lived engagement to actress Brooke Burns, 54-year-old Bruce Willis married 31-year-old Emma Heming.

The couple wed in Turks and Caicos on March 21, 2009, and guests reportedly included Bruce’s three daughters, as well as Demi and her at-the-time husband, Ashton Kutcher. 

Bruce and Emma went on to welcome two daughters, one born in 2012 and another born in 2014.

While Sarah Paulson, 49, and Holland Taylor, 81, first met at a party in 2005, it wasn't until almost a decade later that the two would reconnect over social media and start dating, People reported.

Despite Sarah being the younger partner, it is Holland who slid into the American Horror Story’s star DMs in 2015.

In a 2018 interview with Town & Country, Sarah opened up about the age gap, stating: "I do not want to be defined by who I share my bed, my home, my soul with.

“My choices in life have been unconventional, and that's my business. 

“But I do want to live responsibly and truthfully without hiding. 

“It's complicated, because there is a lot of hate in this world, and a lot of good can come from quote-unquote normalizing something for people who don't see it as normal. 

“Our relationship represents a certain amount of hope and risk. 

“Maybe there's something brave in it. 

“Maybe it encourages others to make brave choices. What else can I say? We love each other."

George Clooney is 63 years old, while his wife, Amal Alamuddin Clooney, is 46 years old, making their age gap a 17-year difference.

According to People, George was at his home in Italy when he was first introduced to the British-Lebanese lawyer and human rights activist in 2013.

Just a year later, Amal and the Ocean’s Eleven star became engaged and, shortly after, obtained marriage licenses in the Royal Borough of Kensington and Chelsea in the city of London.

In June 2017, Amal gave birth to fraternal twins: a girl and a boy, Ella and Alexander.

After numerous rumors of on-and-off engagements, splits, reconciliations, and more break-ups, an insider revealed that Cher, 78, was exploring reconciliation with Alexander “AE” Edwards, 38.

“They had stayed in communication even though they called things off a few months ago,” the source told Us Weekly in September 2023.

They added: “They’ve reached a point where they want to give things a second try. 

“They’re not officially back together yet, but they’re enjoying spending time together again and they make each other happy.” 

The Goddess of Pop first tweeted (now known as posting on X) about AE, a music executive, in November 2022, sharing heart emojis and pictures of him, Elle reported.

Al Pacino, 83, was first linked to Noor Alfallah, 30, in April 2022, and the couple welcomed their first child together in June 2023, People reported.

The Oscar winner had already fathered three adult children: daughter Julia, whom he welcomed with acting coach Jan Tarrant, and twins Anton and Olivia, whom he shares with ex Beverly D'Angelo.

In March 2024, Noor spoke publicly for the first time about her relationship with Al in an interview with Vogue Arabia. 

The Kuwaiti-American producer said: "Al lives down the street from my house and we started spending every day together, playing chess and watching movies. 

"It was like film school with Al Pacino.

"I guess it just became something more."

Harrison Ford and Calista Flockhart met at the 2002 Golden Globe Awards. At the time, the Indiana Jones star was 60 years old and already married Melissa Mathison.

Meanwhile, the actress, famous for her role in Ally McBeal, was 38 years old and had adopted her son the year before.

Harrison, who had four children from previous marriages, wed Calista on June 15, 2010, in Santa Fe, New Mexico, after eight years of dating. 

Matthew McConaughey and his wife, Camila Alves, are 13 years apart. The couple, who have been married for 12 years, first met in 2006 at the West Hollywood nightclub in California, USA.

Matthew, who was 37 years old at the time, recalled being instantly infatuated with the Brazilian model, who was 23 years old then.

"She showed up, and she moved right to left in front of my eyes across that club," the now-54-year-old actor told People of their first meeting. 

He continued: "It was as if she was floating. And I did not say, 'Who is that?' I said, 'What is that?' 

“And then introduced myself. Since that evening, I have not wanted to spend time with any other woman."

Matthew and Camila have since welcomed three children: Levi, 15, Vida, 14, and Livingston, 11.

Jake Gyllenhaal, who is 43 years old, and Jeanne Cadieu, who is 28 years old, began dating in 2018. 

The couple has kept their relationship relatively low-key, rarely making public appearances together. 

Despite their private nature, they have been seen attending events such as the premiere of The Lost Daughter in 2021.

Despite a 25-year age gap, iconic Hollywood couple Michael Douglas and Catherine Zeta-Jones have been going strong for over two decades.

In March 1999, Michael, who was 55 years old, began dating the then-30-year-old Welsh actress. 

The pair married on November 18, 2000, and went on to have two children, son Dylan Michael, born August 8, 2000, and daughter Carys Zeta, born April 20, 2003.

In early April 2018, Richard Gere, who was 69 years old, married Spanish activist Alejandra Silva, who was 35 years old at the time.

In August 2018, they announced that they were expecting their first child, and in February 2019, their son Alexander was born in February 2019.

Alejandra gave birth to their second son in April 2020.

87-year-old Warren Beatty and 66-year-old Annette Bening connected before filming the 1991 crime drama Bugsy, and they have been inseparable ever since. 

The iconic Hollywood couple wed on March 3, 1992, and they went on to have four children together: Stephen Ira Beatty, born on January 8, 1992, Benjamin Beatty, born on August 23, 1994, Isabel Beatty, born on January 11, 1997, and Ella Beatty, born on April 8, 2000.

At 19 years old, Aaron Johnson met Sam Taylor in 2009 on the set of Nowhere Boy.

At the time, Sam was 42 years old and happened to be the director of the 2009 John Lennon biopic movie, which went on to become Aaron’s breakthrough role.

After years of dating, the pair married on 21 June 2012, subsequently changing both their surnames to Taylor-Johnson.

They have two daughters. Additionally, Aaron is a stepfather to Sam’s two daughters from a previous marriage.

Fellow celeb couple Jensen Ackles, who portrayed Jeffrey Dean Morgan’s son in Supernatural, and his wife Danneel Ackles, who starred alongside Hilarie Burton in One Tree Hill, introduced the pair in 2009.

Hilarie, who was 27 years old at the time, was matched with Jeffrey, who was 43, on a blind date at an Irish pub in Los Angeles on May 8, 2009.

A decade later, the lovebirds tight the knot. The actors, who also played each other's spouses on The Walking Dead, welcomed their first child, a son, in March 2010, and their second child, a daughter, in February 2018.

German stars Heidi Klum and Tom Kaulitz met in 2018. Heidi was 45 years old and had already been married twice with four children, while Tom was 29 years old. 

After a whirlwind public romance, the couple announced their engagement on Christmas Eve 2018 and later tied the knot in a private ceremony in Capri, Italy, on August 3, 2019.

Bradley Cooper and Gigi Hadid were first linked in mid-2023. The pair, who have a 20-year-age gap, have kept their relationship under wraps, with few public appearances together.

The 29-year-old supermodel split from Zayn Malik in October 2021, just a year after welcoming their daughter, Khai Hadid Malik, on September 19, 2020.

Meanwhile, the 49-year-old actor split from Irina Shayk in 2017 after welcoming their daughter, Lea De Seine Shayk Cooper, on March 21, 2017.

Following his controversial romance in 1993 with 17-year-old high school student Shoshanna Lonstein when he was 38 years old, Jerry Seinfeld went on to meet his future wife, Jessica Sklar, in 1998.

The stand-up comedian was 44 years old at the time, while Jessica was a 27-year-old public relations executive for Tommy Hilfiger who had just returned from a three-week honeymoon in Italy with then-husband Eric Nederlander.

After filing for divorce, Jerry and Jessica continued dating before tying the knot on December 25, 1999.

The Seinfelds have a daughter and two sons.

Following a nearly decade-long notable marriage with Kim Basinger that ended in 2002, Alec Baldwin began dating yoga instructor Hilaria Thomas in 2011.

The couple got engaged in April 2012 and married on June 20, 2012, at St. Patrick's Old Cathedral in New York City, USA -- The Cooler star was 54 years old, and Hilaria was 28 years old.

Alec and the Boston native have seven children together. Moreover, the family has taped a reality show, The Baldwins, set to air on TLC in 2025.

Following the tragic self-inflicted death of Mick Jagger’s girlfriend, L'Wren Scott, in 2014, the rockstar has been in a relationship with American ballet dancer Melanie Hamrick. 

Mick was 73 years old when Melanie gave birth to their son, Deveraux Octavian Basil Jagger, in 2016, and she was 29 years old.

John Stamos met Caitlin McHugh when he was on the set of Law & Order: SVU in 2011. The Full House star was 48 years old at the time, while Caitlin was 25 years old.

During a 2017 interview with People, John revealed, "I played a guy who was so egotistical that he thought he should spread his progeny, so he had, like 60 kids or something … and Caitlin, ironically, was one of the girls that I was trying to fool and have a baby with."

The couple went on to get married in February 2018 before welcoming their baby boy, William "Billy" Christopher Stamos, on April 10, 2018.

In August 2014, Kris Jenner, who was 59 years old, connected with Corey Gamble, who was 34 years old, while they were both in Ibiza, Spain, to attend the 40th birthday party of their mutual friend, fashion designer Riccardo Tisci, People reported.

The momager was reportedly separated from her then-husband, Caitlyn Jenner, and the former couple was in the middle of divorce proceedings. 

At the time, Corey was employed by Scooter Braun and was serving as Justin Bieber's tour manager.

On an episode of The Kardashians that aired in May 2024, Kris opened up about the beginning of her relationship with Corey after "an amazing almost 10 years."

She said: "I used to say to Corey all the time when I first started dating him, like, 'Why do you want to date somebody who is older than you?' 

“I didn't get the age gap, and then he taught me that age is just a number."

37-year-old Rosie Huntington-Whiteley and 56-year-old Jason Statham started dating in 2010 before getting engaged in January 2016. 

They have two children together: a son, Jack Oscar Statham, born on June 24, 2017, and a daughter, Isabella James Statham, born on February 2, 2022. 

Despite being engaged for nearly a decade, the couple have been rather relaxed about marriage.

An insider told The Daily Mail in 2023: “When it comes to them, they will get married eventually but they feel like they are already married and there is no rush."

"'If it isn't broken, why fix it?' is their overall mentality."

A 43-year-old Ellen DeGeneres first met a 28-year-old Portia de Rossi at a Rock the Vote concert back in 2001. 

Over two decades later, the women are still going strong, having married in 2008.

"[I knew she was the one for me] when I first laid eyes on her," Portia said in an interview with Oprah Winfrey in 2009. 

The now 51-year-old actress continued: "But it took me three years to actually tell her how I felt about her because I was on Ally McBeal at the time and I was not living as an openly gay person."

She added: “I was closeted and very, very afraid that if I talked about being gay, it would be the end of my career. 

“So, I wasn't about to date the most famous lesbian in the world."

Eddie Murphy and Paige Butcher began their relationship in 2012. The Beverly Hills Cop star was 51 years old, while the Australian actress was 33 years old.

The couple have two children together: a daughter, Izzy Oona Murphy, born on May 3, 2016, and a son, Max Charles Murphy, born on November 30, 2018. 

The actors got engaged in September 2018 and have maintained a relatively private relationship since.