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The hot, humid day is far more miserable as far as my personal comfort goes. That said, however, perpetually rainy weather can be kind of gloomy. Regardless of whether it's 80F and rainy or 40F and rainy. So that's another factor to consider. But the 50F and rainy day is far more comfortable.
Voted for hot and humid, but a day in winter with heavy rain and temperatures of 1 to 3°C (35 - 38 F), so that it is a clammy damp cold but still not cold enough for snow to fall, that would be the most miserable weather for me.
Cool and rainy especially in the daytime and between April - September. Rain should fall in brief showers or storms between then. Cool weather is useless then too, with the long daylight hours we have.
For me I feel a cool rainy day is the most miserable. Having said that my dream climate has an abundance of hot humid days in the summer and lots of cool rainy days (10C to 15C) in the winter so maybe I'm just weird.
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