If the real-life love story between the late Rob and Michele Reiner had never happened, one of the most iconic romance movie endings would've looked a whole lot different... Perezcious readers know the 1989 rom-com classic When Harry Met Sally ends with Harry (played by his best friend, Billy Crystal) running into Sally (portrayed by Meg Ryan) at a New Year's Eve party, where he tells her he loves her. But because of their history, Sally doesn't initially believe him, thinking he is only "lonely" and nothing more.