'When Harry Met Sally' stars Meg Ryan and Billy Crystal (1989) Columbia/Courtesy Everett Collection Share on Facebook Share on X Share to Flipboard Send an Email Show additional share options Share on LinkedIn Share on Pinterest Share on Reddit Share on Tumblr Share on Whats App Print the Article Post a Comment Rob Reiner famously cast his mother in a key scene in his 1989 classic When Harry Met Sally - but he now says he may not have realized how awkward directing it was going to be.