Francesca Pascale & Silvio Berlusconi 

This relationship is one of perhaps the most glaring age discrepancies on this list, which Francesca Pascale’s parents weren’t too jazzed about. Their age gap stands at almost 50 years, which is pretty incredible to say the least. Luckily for Silvio, he seems to mask it pretty well.

Photo by Salvatore Laporta/KONTROLAB /LightRocket via Getty Images

And while her parents have voiced their disapproval, remarking in an interview with Vanity Fair Italia that, “We admire him too, but he could be your father,” that never stopped her from pursuing Berlusconi, who has a net worth of about $7 billion. In fact, in the same interview, she said, “I have sought him out; I have courted him; I have made him fall in love and get engaged.”