Cathy Schmitz and Richard Lugner (57 Years)
We’re going to lay this out right away: A bunch of these big age gap relationships are rich as hell older dudes banging hot young models because capitalism is the most powerful force in the universe. Richard Lugner was an 82-year-old multi-millionaire when he wed former Playboy model Cathy Schmitz in 2014. Schmitz, who had previously pursued a TV career, gave everything up to move to Vienna with the construction magnate. She’s not the only young lady he’s squired–the year before, he made headlines by taking a pre-Kanye Kim Kardashian to the snooty Vienna Opera Ball.
Kyle Jones and Marjorie McCool (60 Years)
Some of these relationships are enabled by what is basically a fetish, where the younger partner has a “thing” for wrinkles. A great illustration of this is Georgia man Kyle Jones, who has serially dated older women for most of his life. One of his most notable relationships was with 93-year-old retiree Marjorie McCool, who he met in 2008. The duo enjoy an active sex life despite their 60 year age difference, but it’s not an exclusive relationship — the rest home Lothario dates numerous oldies at a time. He started his first senior romance when he was just 18 and says that he’s not in it for the money — he’s just attracted to way older women.
Valentin Ivanov and Elizaveta Adamenko (37 Years)
Russia is a wild place right now, with lots and lots of money floating around. And where there’s money, there’s people pushing the limits of what’s socially acceptable. Oil tycoon Valentin Ivanov reportedly started romancing child model Elizaveta Adamenko when she was just 14 years old, and the duo wed in 2016 on the French Riviera. The 37 year age difference, combined with the bride’s youth, was enough to make the press take notice, but Adamenko made a statement insisting that she was marrying her 55-year-old paramour for love, not money. Interestingly, she’s since purged her social media of many of the pictures of them together.
Saneie Masilela and Helen Shibangu (53 Years)
The wedding of nine-year-old Saneie Masilela isn’t a traditional romantic one. Instead, it’s rooted deeply in the superstition of his South African family’s native religion. Saneie claims that he was visited in a dream by his ancestors, who commanded him to marry the older woman. Never mind that she was already married to a man her own age — when the ancestors tell them to do something, they do it. Amazingly, the age-gapped duo actually had a pair of weddings, one in 2013 and a second in 2014. The duo don’t live together or make out or anything — it’s a symbolic marriage only.
Marilyn Buttigieg and William Smith (29 Years)
Many of the dudes in this article who go for older ladies can trace their fixation back to childhood, but British man William Smith took it a step farther than that by actually marrying his best friend’s mother. Will met Marilyn Buttigieg when he was a teenager and was immediately taken with her. It didn’t matter to either that there was 29 years between them, but some family members weren’t quite as enthused. Most notably Marilyn’s husband, who she dumped for the younger man. Their relationship seems a lot stronger, though, as they’re still together after seven years of marriage.
Hugh Hefner and Crystal Harris (60 Years)
No list of May-December romances would be complete without Playboy publisher Hugh Hefner, who has been dating women in their 20s consistently, no matter how much older he got. In 2012, Hef married lovely blonde December 2009 “Playmate Of The Month,” Crystal Harris, on New Year’s Eve when she was 26 and he was 86. Harris wanted a little security in her life, despite Hefner’s profligate ways, and the marriage has lasted a while. Harris signed an ironclad prenup that means she won’t get anything from Hefner’s estate when he passes away.
Edna Martin and Simon Martin (38 Years)
We don’t want to throw shade, but if you’re 39 and still living with your parents, your romantic options aren’t really the best. So when Simon Martin met Edna at an organ concert in 2003, the pair maybe bonded a little tighter than normal. The dyslexic, partially deaf and developmentally disabled young man had absolutely no romantic experience beforehand. That said, the duo shared an incredible interest in music, and Simon’s potent keyboard skills charmed her to no end. They struck up a romance and shocked the world when they wed in 2005. Their significant age gap hasn’t had much effect on their marital bliss, as they proudly boast about having a healthy sex life.
Gary Hardwick and Almeda Erell (53 Years)
Love can blossom in unlikely places — like a funeral. That’s where elderly Almeda Erell met the teenager who would become her husband. Gary Hardwick has had a thing for older women ever since getting a crush on his elementary school teacher, but when he met Almeda at the funeral of her son, it was an instant connection. The pair had a second date at Chuck E. Cheese’s and it wasn’t long before the 18-year-old Hardwick dumped his 77-year-old girlfriend for the 71-year-old Almeda. The pair were married soon afterwards, and have set up a YouTube channel to share their unusual romance with the world.
Woody Allen and Soon-Yi Previn (36 Years)
Hollywood has plenty of older man/younger woman romances. The very nature of the movie business means that dudes are always trying to trade in last year’s model for some new arm candy. But the disturbing tale of director Woody Allen and his wife Soon-Yi Previn makes the list not only for the 36 years between them, but also for the disquieting circumstances that led to their marriage. You see, Previn was adopted by Allen’s longtime paramour Mia Farrow in 1978 at the age of seven, and he helped raise her like a daughter. That is, until Farrow discovered nude pictures of her in Allen’s things and realized the pair were in a sexual relationship, with Previn 21 and Allen 57 years old. Astoundingly, their marriage has somehow stood the test of time.
Ahmed Muhamed Dore and Safia Abdulleh (95 Years)
The biggest age gap ever recorded by the media is a staggering 95 years, where a man who was reportedly 112 years old took a 17 year old bride in Somalia. Ahmed Muhamed Dore was a fascinating dude, with five other wives and 114 children and grandchildren. His oldest son is 80 years old, which lends a little credence to his claims of advanced age, but his traditional goatskin birth certificate can’t be authenticated. Safia didn’t have much to say to the media on her special day, but she seemed to enter into holy matrimony willingly. Ahmed claimed, “I used my experience to convince her of my love,” which is a pretty good line.