8. Anna Nicole Smith And J. Howard Marshall

Anna Nicole Smith is probably one of the first women that come to mind when thinking about celebrities who dated men that were way too old for them. Smith notoriously married J. Howard Marshall, a man who was 63 years older than her, at the age of 26. She met the oil tycoon while working at a club in Texas. Her 89-year-old husband died in 1995, just one year after their wedding, leaving Smith to be a widow in her twenties.

Much to Anna Nicole’s surprise, Marshall had not left anything to his new bride in his will. After years of battling in court and attempting to gain access to some of her dead husband’s fortune, Smith died after struggling with addiction and weight issues in 2007.

7. Bella Thorne And Scott Disick

After his breakup from the mother of his children and longtime partner, Kourtney Kardashian, Scott Disick seemed to go slightly off the deep end. The reality star was spotted partying with a new woman every day, traveling around the world drinking and doing drugs, and being photographed in provocative shots on a daily basis. This past summer, the 34-year-old was snapped by the paparazzi in Cannes canoodling with 19-year-old Bella Thorne.

The two were caught in a number of photos looking more than comfortable with one another. Although the fling was not long-lasting, people would certainly talk about it for months to come. The former Disney star swears that the relationship was platonic and the two were strictly friends but a picture is worth a thousand words…

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