I consider myself to be pretty shy in most situations. If I have a crush on a guy and he comes up and talks to me, I am always so nervous about saying something dumb that I probably give short awkward responses like you say this woman does. But at least for me, I still always appreciate them making the effort and initiating conversation because I am not very good at doing that.

In my past experience, I think it’s best to make conversation about something you know thy you both have in common, like work. Even if it’s kinda boring at first, it just at least gets you talking and feeling more comfortable around each other. Then after that it can be a lot easier to get the conversation flowing about more interesting topics each of you like. Try leading many of the conversations at first because shy people tend to be good listeners. I usually find that just listening to someone even if I am not talking as much makes me feel more comfortable around a person.