It usually takes a while for me to warm up to people. Some longer than others, but given enough time and interaction, there's often a transition when someone stops being a stranger and it hits me that hey, I actually really like this person. He/she is pretty cool. Consequently, my internal shyness goes away. This has naturally happened in all of my friendships, mostly in a gradual process.
It's rarely a definitive moment, but I had one of those today.
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