OP's condition said it was social anxiety than social awkwardness to which my post was asking for a more overall solution to social issues.

To answer your question, I think his sessions were pretty beneficial but I think missed one thing that I believe therapists should be aware, some socially awkward people are oblivious. There's body language [0], there's ways of talking about or asking for things (don't do it directly sometimes) [1], etc. Some people can't magically overcome that when meeting people but I believe they can learn (at risk of exacerbating their self-consciousness).

[0] How Do You Use Body Language to Read Minds?; http://www.chacha.com/content/infographics/how-do-you-use-bo... (It's said to be inaccurate, I'm not sure either)

[1] RSA Animate - Language as a Window into Human Nature; http://www.youtube.com/watch?v=3-son3EJTrU