I was approached by a guy on the street we were just passing by against each other. he noticed me and stopped me to give a compliment. I felt strange and wierd because it was all of sudden. I never saw that guy before.
It looks creepy actually in general.
Seems I was not a random person we live near to each other (saw him again after few weeks passing by at night without making any eye contact but I felt it was him) so he has seen me quite a few times.
For showing guts to approach and tried to initiate conversation, I will say 10/10 for making efforts.
But I will say should not do it.
If u made an eye contact and she also made it and u both smiled at each other u can say hi.
Take it slowly. Start with waving hi then gradually approach and talk to her.