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Is it possible to sort all Gmail contacts by contact frequency, either directly from Gmail or using a external tool/service? How?

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Not in GMail. The only free consumer service with a similar function is Gist. It allows you to sort contacts by "Importance" (overall frequency & depth of conversations) and by communications sent/received to/from a contact. However, it scans only the last 30 days of communication history for new accounts. Everything else is expensive enterprise customer relationship management software.

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You can also have a try at xobni.

It had this functionality on Outlook, I do think it will work for Gmail too. And it adds a lot of funny (or useful) features.

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