I think the confusion is "free as in beer". I guess the idea behind it is that your friends going out drinking will pay for your beer so you get the beer gratis

I think the confusion is "free as in beer". I guess the idea behind it is that your friends going out drinking will pay for your beer so you get the beer gratis. To anyone hearing the word "free as in beer", their first thought is that "beer is not free, I have to pay for it". Whereas the statement "free as in speech" is descriptive, the term "free as in beer" requires you to interpret the price of beer in the exact opposite way it's usually understood. I seem to remember a story about visiting hackers going out for drinks and the expectation was that the people they were visiting would pay for the drinks, but I can't find that story now. I was under the impression that "free as in beer" was a cultural idiom which, if true, would make it further understandable why people not familiar with hacker culture wouldn't have the context to make the "free as in beer" expression make sense.