The Shop Around the Corner (1940)
Two employees at a gift shop can barely stand one another, without realizing that they’re falling in love through the post as each other’s anonymous pen pal.
This is one of my favorite Jimmy Stewart movies. He plays a store clerk that has come to a point in his life where he wants a little bit more out of his life. So naturally he answers a personal ad in the paper.
One thing leads to another and he falls in love with the girl he writes to, evidently the idea of it being a dude doesn’t enter his mind. Such a trusting time. When he finally gets to meet her, he’s nervous that she’s going to be fugly, then he finds out it’s the woman he works with and hates.
Since it’s Jimmy Stewart and he’s not a total dick, though I’m not sure if anyone’s a total dick, he ends up wooing her as himself and not just through letters. It’s beautiful.
I do think Margaret Sullavan’s character is a bit of a bitch at times. There are also some dark moments, attempted suicide and infidelity, though, not from Jimmy or Margaret. It’s a great story and a nice look at depression era sensibilities.