Therapy is to help us in our actual lives. What you learn in therapy you then have to go practice out in the real world. I do not understand why you are not ordering coffee 10 times a day if that's what you want to get good at? I had trouble relating to others/socializing so I practiced with talking to grocery clerks, librarians, anyone I could. What is scary we have to do until we understand why it is so scary and then some more so it becomes more routine and less scary. Insight from process alone won't help us, putting the insight to work and redeveloping it so what happened before isn't happening now is what helped me (during and after therapy, 1970-2005).
My husband loves ice cream but I would not go to Baskin Robbins or elsewhere with him for ice cream. One day we were in the Mall and I did get an ice cream cone. I also got extremely anxious! Because of where I was in therapy, I got an insight: my stepmother use to "punish" me for getting messy when eating ice cream. I was only five or six and could not lick the cone fast enough (and, back in the 1950's, you generally only got ice cream in summer) and to make matters worse, my brother 2-1/2 years older than I was was able to eat his cone fast enough so did not get messy. So, there I was in my mid-40's feeling anxious about getting messy (still don't "like" submarine sandwiches because of all the dressings and stuff oozing out!) and not being able to lick my cone fast enough. Well, I was also well enough along in therapy to be able to laugh at myself; who cares if I get either messy or can't lick the cone fast enough??? I'm a big kid now!
Order the coffee often as an experiment! See what is making you anxious. Is it worrying about the other people? Why worry about them; you don't know them or they you! Are you afraid of the clerk? Afraid they won't give you what you want, will misunderstand you? Or, maybe they won't "like" you and will be mean to you? They, too, don't know you so don't have any valid reason to not like you; we can "decide" how we think other people are, why not decide that the person is nice and wants to help? Practice changing your assumptions about people; even the same people :-) Go for a walk on a busy street or in the Mall and practice just saying, "Hey" or "Hello", or "Hi" to people you pass or even just looking at them deliberately and smiling. There are so many fun things to make up and do and no one has to be the wiser! You can see if people smile/say "hi" back and speculate on "what kind" do/do not. It's almost like sitting and making up stories about what people do for a living; being aware of what our own heads are doing versus what is checked out by asking another. We can't know what others are thinking/feeling unless we ask them; that's the ONLY way we can know for sure (or if they spontaneously tell us what they are thinking/feeling).
Before therapy I was really really bad at "reality-testing":
http://dictionary.webmd.com/terms/reality-testing but learned through therapy how to separate what's me and what's not me; who I am and what I'm responsible for. But putting what I learned in therapy into practice was the most difficult part of therapy. Just showing up each week was the "easy" part, relatively speaking.