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I am trying to help someone break the habit of delaying too long in replying to emails. For a select group of email senders in Gmail, I'd like to set up some way of seeing how long it has been since the last received email that hasn't been replied to, and then sort that list by the longest period.

In essence, this is a per-person stopwatch counting how long it has been since email from that person was received. At the top of the list are the people that have been waiting longest for a reply (longest running stopwatch), and at the bottom those that have just recently sent email (shortest running stopwatch).

When I reply to someone they drop off the list until they in turn reply, at which point they come in at the bottom of the queue again (stopwatch resets).

Is there a way to configure a filter, mailbox view, or some other sort of report in Gmail (or some tool that plugs into Gmail/IMAP) that could show a view like this?

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This would be a great feature for me too, but AFAIK it doesn't exist.

My solution to cope with such a problem is to use the service called Boomerang. What I do is that I empty my inbox as much as possible multiple times a day (at least once). For any email that would take me longer than 5 minutes to write a response to, I delay it: I ask for it to be "boomeranged" when I'll have time to deal with it (perhaps tomorrow morning very early, so that I handle it first thing in the morning, as it appears at the top of my inbox).

Often enough, I find myself delaying emails that I know don't need a quick answer (for e.g. someone invites you to a party in 2 months...), so I used to procrastinate and end up not answering. But if I boomerang it right when I'll have to reply (say a week before the party), I force myself to answer the email at the best time for me and the recipient.

Note: I'm not affiliated with Boomerang, just a happy user.

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Unfortunately, what you are asking for is not possible. GMail has no such feature.

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