My top picks off the top of my head for my most awkward moments are
When I'm on the escalator and you try to look anywhere but the girl in front of me.
Or when I'm left alone with someone I don't know and I try to make small talk and it goes something like "Hi" "Hi" "Hru?" "Good,you?" "Good" "...".
Or when a girl is taller than me and I have to ......
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