The two partied at Vignette Lounge on March 20. At the end of the night, they left the hotspot separately—but they didn't stay apart for long! Ashley, 26, was spotted hopping in 38-year-old Ryan's car before they roared off into the night.
"She was at pains to hide her face from onlookers," reports Mailonline.com.
Ryan hasn't had a ton of luck in relationships since he and Reese Witherspoon divorced in 2007. He dated Abbie Cornish for a few years before they broke up in 2010. Most recently he's been linked to college student Paulina Slagter, 21, and Amanda Seyfried.
Five months ago, Ashley split with her singer-songwriter boyfriend of ten months, Reeve Carney.
Do you think Ryan and Ashley would make a cute couple if they take it to the next level? Tell us in the comments section or on Twitter @OKMagazine