When to compliment a woman’s beauty?

ubergo150
So I’ve been dating this girl a while... and things are pretty solid, but I’ve told her she’s cute or pretty a few times and it always seems to land a bit awkwardly.

When have you noticed is the best time and place to organically compliment someone? I’ve told her she’s really funny and smart, and I’m honest about that too, she is... but how can I compliment her beauty without it being awkward?
When to compliment a woman’s beauty?
When to compliment a woman’s beauty?
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