Background: Kudos to /u/Ciaran_Callam for starting 100 Women in 50 Days. Inspired by him, I decided to embark on this challenge as well and thought of posting my experience.

 

Woman 1

As I stepped out from my office building I see this okayish looking woman walking in same direction with me. She saw me and continued walking. She was trying to find something in her handbag. I took 2-3 steps and thought to just start a conversation.
Me: Hi, <she turns towards me and looks at me>, I see you often around this time. Do you work closeby?
She: <loudly> I am not interested in talking (to you - don't remember if she said "to you" or not)
Me: Fair enough.

 

Take Away Don't think I could have done anything different here. The bigger issue is that awkwardness of seeing her everyday which makes me think again approaching someone on my daily routine. It's been with 2 people now who have bluntly stopped me and whom I see everyday.

 

Woman 2

This the most blunt conversation I had so far. Conversation started out good but within 2-3 sentences she said "Why you're even fucking still here? Just leave". Honestly this was damaging.

Take Away Be proactive in first 2-3 sentences and if you sense things won't work out then don't even share your intention of hitting. Just say you're new here and ask for recommendation. This experience was shattering.

 

Woman 3

A beautiful tall woman crossing street. I was with my friend and told him that I have to approach her. Having friend this time actually boosted my confidence. I ran towards her from the opposite side of street.
Me: Hey
She: looks towards me Hi with a smile .
Me: I noticed you while you were crossing the street and think you are cute. So wanted to say Hi.
She: Thank you. I am ABC.
Me: I'm XYZ. Are you into modeling or something? You have this bold posture and come across as a confident person.
She: haha That's so sweet of you. I am actually a wedding planner.
Me: I see. Do you live around here?
She: No. I am actually visiting my family. I am originally from Oregon.
Me: Cool. I don't wanna take a lot of your time. I would love to take you out on a date.
She: haha. Sorry I am engaged.

This was bummer. I didn't see her engagement ring.

Me: Well I must say your fiance has a good taste in woman. Anyways good to meet you.
She: Same here. Bye.

 

Take Away She was one of the most beautiful woman I have approached so far and it was not at all scary. Still need to work on how can I lead a conversation without showering compliments all the time.