How often do you see a woman you want to talk to but come up with excuses about the context, she seems busy, you can just seat at her table, etc...

The question for me is: if I knew this person, would I feel comfortable talking to them? If yea then the issue is not the context but how I relate to people.

At the end of the day, we are all human beings, and unless you recognize that, it will be very hard to feel at ease talking to people no matter the context.

For me talking to people, whether a woman I find attractive or a random old man on a bench is a mental exercise in presence, going into the moment and staying as relaxed as if I am hanging out with friends.

So let's forget the tips and tricks, just go as you are and see what happens :)

Check out this interaction to illustrate my point :)

https://www.youtube.com/watch?v=BExa0VWWgkQ