DAVID SCHWIMMER AND ZOE BUCKMAN

David Hasselhoff always played the one-woman man in every TV appearance, and such is true in his personal life. When the celebrity hit 43 years old, he tied the knot with long-time girlfriend Zoe Buckman, who was only 25 at the time.
Their romance started budding when the two met at a club in London’s West End where Hayley was a waitress and David was a regular customer. Soon, Zoe moved to Los Angeles to stay with David and marry in a private ceremony. Sadly, the love birds later called up their divorce lawyer and called it quits in 2017.

JERRY SEINFELD AND JESSICA SKLAR

Jerry Seinfeld and Jessica Sklar’s started after Jessica divorced her ex-husband a few months following their honeymoon. It was indeed a messy start for the two, as Jessica reportedly initiated the separation to pursue her relationship with Jerry. Their 20-year age gap didn’t help quiet down the public either.
The two were indeed deeply in love and enjoyed each other’s company. It wasn’t long before they finally got married in 1999. Jerry only has good things to say about his wife Jessica, who he consistently describes as funny, sarcastic, and witty. They’re now focusing on building their insurance and raising their three children.

SYLVESTER STALLONE AND JENNIFER FLAVIN

For Sylvester Stallone, his wife Jennifer Flavin could simply do no wrong. She was in charge of making the right decisions and keeping up with their money management. Indeed, his trust in his wife must be the secret to their happy 22-year marriage.
Sylvester shares that he enjoys living with his wife, and how he continues to learn so much from her. The two first met in 1988 when David was 42 years old and Jennifer was 19. Throughout the two decades of staying happily together, they’ve been an inspiration to many couples who are just entering the married life.

HUMPHREY BOGART AND LAUREN BACALL

When Humphrey Bogart and Lauren Bacall started dating, fans were excited to see where the couple was headed. The two were even called “Hollywood’s greatest romance” because their story was enough to inspire song lyrics. Bankruptcy and divorce were nowhere near the couple. Despite the huge age gap, they still made it to the altar when Humphrey was 44 and Lauren was 19.
Their marriage adventures were indeed one for the books. After they celebrated their 13 years of marriage, Humphrey sadly passed away of esophageal cancer. Up to this day, Lauren sees their Humphrey as her first and only true love.

ROBERT DUVALL AND LUCIANA PEDRAZA

Robert Duvall and Luciana Pedraza’s relationship is probably the most unconventional of the bunch. The couple has been dating since 2010 after meeting on a normal day in a bakery at Argentina, but their age gap has definitely raised eyebrows among fans. Luciana and The Godfather actor share the same birthday, except Robert was born 41 years earlier.
Their 41-year age gap sparked controversy in the entertainment industry, but the couple has been happily married since 2005. While Robert was hesitant at first, he eventually allowed himself to pursue Luciana. They surely won’t be calling their divorce attorney anytime soon.

WARREN BEATTY AND ANNETTE BENING

Warren Beatty and Annette Bening hit it off immediately after meeting at a production for the film Bugsy. They got married in 1992 and have been together since. In a recent interview with Us Weekly, Annette happily shares how their marriage has been beautiful with their four children. Warren and Annette seem to agree on quite a lot of things, including household duties like money management.
Warren was the first to reach out to Annette when they worked together in 1991. He asked her out to dinner. A year later, the two told their vows and have been together for almost three decades.

DEREK JETER AND HANNAH DAVIS

Fans believed that Derek Jeter wouldn’t settle down. Because of his success and impressive credit score, the sports world bachelor was on the dating scene throughout his career. He never stayed in a long-term relationship. To everyone’s surprise, the former New York Yankees athlete soon entered a serious relationship with swimsuit model Hannah Davis.
Hannah was 16 years younger than Derek, but the two were indeed very supportive of each other’s careers. A common friend even described Hannah was having “wisdom beyond her years.” It’s no surprise that in 2016, Derek and Hannah finally tied the knot and welcomed their baby girl a year later.

JULIUS ERVING AND DORYS MADDEN

While Julius Erving had a stellar career and heaps of investment money on the bank, his personal life was the subject of controversy. The professional basket player was a ladies’ man, and his relationships made entertainment news headlines. However, he had a wife, Turquoise, and four children waiting at home.
Outside of his marriage, Julius was father to two children with two different mistresses. His second-born was with Dorys Madden, his mistress who was 19 years younger. For the couple, it wasn’t a one-time thing. Julius and Dorys eventually tied the knot in 2008 after Julius finalized his divorce from Turquoise.

MICHAEL JORDAN AND YVETTE PRIETO

Michael Jordan had a rough time with his previous marriage that ended in a $150 million divorce settlement. However, his controversial past didn’t stop the basketball legend from giving marriage another try. This time, the athlete settled down with Yvette Prieto, who was 15 years his junior.
The high-profile couple got engaged in 2011 and tied the know 2 years later in Palm Beach, Florida. At the time, Jordan was 50 years old and Yvette was 35. With his success and investment planning, we’re certain that Michael’s family – his wife Yvette and their twin daughters Victoria and Ysabel – have a comfortable life ahead of them!

WLADIMIR KLITSCHKO AND HAYDEN PANETTIERE

Wladimir Klitschko and Hayden Panettiere are proof that opposites do attract. From their difference in age to their views on credit cards, even Hayden was well aware that they were an odd match. The couple first met at a book party in 2009 when she was fresh from a breakup.
During their relationship, Wladimir and Hayden hit a rough patch and called it quits. It wasn’t until 2013 when they reunited and eventually got married. Despite their 13-year gap, it’s been smooth sailing since. They are now looking to grow their family after welcoming their first child together in 2014.