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Is there a SO family + SE site where I can ask questions related to fonts and also font recommendations?

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up vote 1 down vote accepted

Take a look at http://ui.stackexchange.com/ - but search first and look for any existing questions.

In fact there's already a question that might fit the bill - http://ui.stackexchange.com/questions/114/what-fonts-are-good-and-which-ones-should-we-avoid-for-our-applications-ui

However, font recommendations can be subjective so be careful how you word your question (if you do decide to post) and try to make it as objective as possible.

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What about a "Which free font do you think goes best with a Happy Birthday card?" kind question? – Lazer Aug 23 '10 at 5:36
    
@Lazer - probably not the sort of expert question we want, but you could ask and see what happens. – ChrisF Aug 23 '10 at 11:44

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