It actually means to spend money extravagantly. ‘Splash out’ is another phrase that sounds like it’s associated with water. I’ve been saving for a rainy day and now I can afford to splash out. 'Who rained on his parade' is a question that means 'What made him so gloomy/depressed/grumpy' 'Dont rain on my parade' means 'Dont try to discourage me' or 'Dont be critical/sarcastic/pressimistic about my plans'.
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