Strange Hollywood hookups: celebrities you never knew dated

Dax Shepard reveals he once dated Ashley Olsen: "She's fantastic"

Stars Insider

02/03/22 | StarsInsider


We all have relationships we'd like to leave in the past, right? Hollywood A-listers are no different! There have been plenty of celebrity romances that were (almost) lost to the annals of history. You'll be shocked at some of these unexpected pairings.

In a combination we'd never even imagine, Dax Shepard recently revealed that he once dated Ashley Olsen. On the February 28 episode of his podcast Armchair Expert he told co-host Monica Padman, "I dated Ashley Olsen and she's just the most wonderful person. She's fantastic." He acknowledged that even at the time some people thought they were "a pretty weird pairing," but he said she's really "just super funny and sarcastic and intelligent."

And, of course, he was also "kind of thunderstruck with the beauty" when he met her at a party. The actor admitted that prior to the meeting, and very importantly, he had never watched 'Full House,' because, he explained, "I probably wouldn't have been able to be attracted to Ashley if I knew her as a baby."

As for her current success in fashion, Shepard noted that while they dated she was invested into the launch of her and her sister's line The Row, and he got to watch them be the "f—ing major bosses" they are. 

And regarding what the former couple actually bonded over? Shepard says part of it was a love of cars. Ashley apparently owned a black Cadillac DeVille DTS when they were dating, and Shepard noted, "I wouldn't mind reconnecting with her to find out if she has that DTS." 

This is just one example of the strangest, forgotten romances in Hollywood history. Click through the gallery for more. 


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