Hey, everyone, 34 y/o male here with a question or questions about whether or not I'm doing something wrong. A few months ago I asked a woman out for a coffee date. She said sure, so I made repeated attempts to schedule a time with her since we work near each other but in different offices and our work loads can vary. She always said "yes" or "sure", but one day my boss came to me and said this woman told him I made her feel awkward. She never once said anything to me.
  To be fair, I can be "different" because I sometimes have issues reading social cues/norms as well as having anxiety when talking to a woman I want to ask out. When I approached her to ask her out, I asked "How are you ladies doing today?" because she was with a friend of hers. I then asked if she would like to have coffee with me to which she replied sure. Some weeks went by with me asking once every few days or so, but she always seemed to have a reason not to.
  After the incident with my boss she and I no longer speak to each other when passing in the halls, but she always seems to be so friendly with everyone else in the world. I also still think she is one of the prettiest women I've ever seen, but I am not going to pursue things with what happened.
  Does anyone have any suggestions on what I could try next time I want to talk to a lady? I am honestly so confused as to how any of this happened that I don't even have a specific direction in which to go with this.
 
  Thank You,
    MeanderingMusing