Thank you. I do agree these are great suggestions, however, I would like to review the process of thoughts that were in my mind, at least at that time, of what I was thinking of talking to her about:How about the next time you see her you figure out a way to engage?
I would ask her how her day is going or some such, she will most likely talk about being tired or wishing she was off as is often the case with service workers.
Then you could say: “oh so what would you be doing if you were free today?” Her answer will most likely give you some insight about the things that are important to her. Maybe she wishes she was out for a hike, or she likes to bake, or she would like time to play with her dog.
This gives you an open. Like maybe “oh I love hiking, I recently discovered this trail (or lake or whatever that’s really pretty) we should go for a hike together, when are you off?” You’re a smart guy @corrector, and a good conversationalist surely you could strike up a discussion leading to meeting her off work for something fun.
The trick is to get them to talk by showing interest in something about her other than her fine cleavage. Let her talk, if you are eloquent and smart you can keep it going for more than a few sentences. Also, I do not know if coffee shops have tip jars in Canada, but you could make sure that she sees you tipping her as well - this shows class and gets noticed. You need to find subtle ways to set yourself apart somehow. And smile, always smile women love a smile.
Just some ideas for you.
1) Noticed it was very quiet around, no other customers around within the space, just me and her. "It's rather quiet around here now, was it busier earlier today?"
2) She had an exotic type of mixed look. "May I ask where you are from?" As I'm mixed myself, if she has a good attitude, it could be an interesting convo.
The reason I'm mentioning this to you, is that is what I had to work with at that time. Even the best idea now can't change the past and circumstnaces which may have caused me to "gulp" saying something (ie that should appear to be reasonable) to engage on her and just stick on this business-mode and don't get where all of the anxiety and fear is coming from. There may be some serious issues with "inner game" since I should have said something, and I felt "blocked", like it was somehow inappropriate, when it's in fact totally appropriate.
Therefore, good ideas are always great on paper, however, with execution, there are sometimes these anxieties and mental blocks that I'm not performing as well as I should. If I can somehow manage the nerves then hopefully I'll take social risks so it's not just about business.