As we all know he is a veritable encyclopedia of classic movies, so he might know what your thinking of.
And though your description is different, it actually hints of Enchantment from 1949, with David Niven and Teresa Wright. It's a beautiful love story, definitely a tear-jerker. If your memory is muddled by time it could actually be this movie. If your memory is clear, it's not, but you'd love this movie if you like the one you're searching for as much as you did. Check out the synopsis and trailer on TCM website. Better yet, watch it! Good luck.
Old Romantic Tear-Jerker Film
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I would suggest picking Robert Osborne's brain about this at http://www.robertosborne.com .
As we all know he is a veritable encyclopedia of classic movies, so he might know what your thinking of.
And though your description is different, it actually hints of Enchantment from 1949, with David Niven and Teresa Wright. It's a beautiful love story, definitely a tear-jerker. If your memory is muddled by time it could actually be this movie. If your memory is clear, it's not, but you'd love this movie if you like the one you're searching for as much as you did. Check out the synopsis and trailer on TCM website. Better yet, watch it! Good luck.