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Winona Ryder and Tom Green were spotted going out on a date in 2008.
There's a picture in American mag The People and also in Tuesdays Daily Mirror 3AM column, reportedly showing Conor snoggin' headline-grabber Winona Ryder (yes, from Ed Scissorhands and Heathers and lots of other great movies), in a parking lot in LA.
Bill Hoover, who was in attendance, invited Oberst to come back to play with him a couple of weeks later.
In that short amount of time, Oberst wrote enough songs to fill out the set, establishing himself as an artist.
It's not hard to get jealous of these men that Winona Ryder has gone out with, so try your hardest to contain your envy.
This is a list that features Winona Ryder's famous exes like Johnny Depp and Matt Damon.