Ashley Olsen & Richard Sachs
So about that double date…these two were not dating for long, but they definitely made some noise during their brief romance. Ashley Olsen is 28 years younger than Richard Sachs. The two kept their dating life on the low, but once they were spotted out with Mary-Kate, things became very public. Sadly, love did not overcome all, and the couple broke up in March 2017.
Ashley Olsen & Richard Sachs
Olivia Wilde & Jason Sudeikis
These two connected instantly! Back in 2011, Olivia met Jason Sudeikis, and they got engaged only two years after. Despite never formally marrying, they had two kids together. There’s a nine year difference, and in case you’re wondering, yes, Jason is older. However, this seems inconsequential to their strong love.
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Olivia Wilde & Jason Sudeikis
