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So I have a site that has live messaging system to chat with other users in realtime.

How often should I EMAIL them saying "You have a new message on ...". If they are heavily chatting it would obviously be a nuisance, so some example rules I've considered to email if:

  1. first message in conversation
  2. first response in conversation
  3. last message was > 3 hours ago (filters out heavy chatting)

It 3 hours too much? too little? Would the ideal rules be something different?

Alternatively, there could be a checkbox "Email this message" that the sender can check on (which resets after each message). Is that a good idea?

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  • My personal preference is 0 Mails per year. You can give the User a choice if he wants emsils but you shouldnt bother when he explicitely says no – BlueWizard Jun 11 '15 at 14:22
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Always give users control

Our inboxes are overloaded as it is. You're right to worry. You have to provide notification for those who come and go, but you can't force on the regulars or people who end up linked to a popular discussion.

Stack Exchange provides a good pattern

A checkbox to activate email subscription:

email notification check box

And in-line settings to control frequency and delivery address:

enter image description here

How it applies to chat

A chat or real-time discussion app can follow the same logic, but it should exist in an easily discoverable (or directed) settings panel/page. The user needs to have notification options for

  1. No notifications: this should be the target if you aspire to a "sticky" experience
  2. Time period "digests": hourly, daily, weekly.
  3. Immediate.

Don't forget the user who loathes email. You could conceivably support SMS, direct Twitter messages, Snapchat, or some other messaging service of the moment.

The Twitter model

I think it's over the top, but Twitter is a good conceptual match for what you're doing and supports extensive email notification tweaking. This is all real time updating, but the idea of event-based notifications might fit your app.

Twitter email notification settings

Fitting the application

In response to your follow ups ...

It's rare to find a model in the wild that perfectly suits your unique intersection of use cases (unless you're copying someone entirely). You'll always find exceptions to the other app's rule.

In your app, it sounds like you'd want an option for
Notify me of the first message from a user
OR
Notify me of the first message from a user in ___ days

I'd also challenge the assumption you mentioned that users won't want to limit frequency to digests. If your site generates a lot of activity (who doesn't want success?) users may only want to get sidetracked by a new chat at certain intervals, like I mentioned in point 2 above. (Time blocking is a well-known practice among people more efficient than me.)

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    Thanks for the answer. It's related but not exacly my use case. Stack is a forum with posts, answers, etc. My app is a realtime chatting application.. such as a dating site. When the user gets a chat message from a new user they should definitely be emailed letting them know, however that doesn't mean they should automatically be "subscribed" or "unsubscribed" from further notifications. – parliament Jun 9 '15 at 20:26
  • Also "daily" or "hourly" doesn't make sense for my use case, they should ALWAYS get it instantly, but the frequency of which it's actually sent is the question. For example, if they simply forget to answer it might be in their interest to receive a second email notifcation on a subsequent message, but as long as a an acceptable amount of time has passed (for example if the sender sends 10 messages in a row, it should only email once), so the question is in the ideal interval and related rules. – parliament Jun 9 '15 at 20:26
  • Of course it makes sense to give the user control to "MUTE" the conversation and stop receiving emails, however this shouldn't be on by default nor should the user get email for every message, until they take the action to turn it off. The use case here is important so I'm looking for answer that's more in line with a real time chatting app – parliament Jun 9 '15 at 20:30
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    I'll ammend the answer to clarify the application. – plainclothes Jun 9 '15 at 20:30
  • I'd like to give you more credit but I'd hate to ask the same question again, as the answer still doesn't address my usecase. In looking at the twitter model the only option that is related to what I'm talking about is "[ ] I'm sent a direct message". In other words, they either obscure the meaning of that or they literally send you an email for EVERY SINGLE MESSAGE you get. So if I sent you 10 email in a row it would send 10 emails? This is exactly what I'm trying to avoid. And I mentioned time period like daily, monthly, dont make sense because they should ALWAYS get the email immediately. – parliament Jun 9 '15 at 20:55
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Take a look at the major players like twitter facebook etc and understand when emails are informative or just annoying.

As an example if my friend sends me a message (even if its the first one) i wouldnt expect to get an email to tell me about it.

Also concetrate information in a daily/weekly email to make users know what they missed and not what they ignored.

In my opinion facebook does not does this well seeing the massive amount of spam they send your way just if someone tags you somewhere but as long as you can disable it and the preset isnt abnoxious ,most things are OK

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  • Well yes but instead of signing up to a dozen sites and fiddling with them I'm asking here :). But you mention one fair rule: when users are "friends", should not send email. Noted, thanks. – parliament Jun 9 '15 at 21:16
  • Also my site has no concept of "friends", only followers/following like on Instagram so it may not apply. It's mainly used to connect with people you don't yet know. – parliament Jun 9 '15 at 21:17
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    Yea,but shouldn't people be using your website to find these people and not their personal email service? If someone doesnt use your website to check out these new people ,whats the point in notifying them that they got a message? Wouldnt an inactivity notifier email be better for that purpose instead of acting like the user is currently using the website and is "missing out" – downrep_nation Jun 9 '15 at 21:21
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    I'm not sure I understand your argument. I have a CoFounder's Lab account but I rarely log into it. Only time I come on is when I get an email saying I have a message from someone. It's regarding someone interested in my profile and wanting to connect, so I want those emails even if I don't actively use the website on a daily basis. Similarly, on a dating app I would like to know of messages I get. My use case is similar. I'm looking for optimal rules to reduce their frequency but not eliminate them entirely like Facebook did. Facebook already knows you'll be back soon lol. – parliament Jun 9 '15 at 21:31
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    Of course you will need to study your userbase and their behaviour. On a dating app where you dont do anything but wait for messages emails make sense,but when not actively using the app means you arent expecting an email ,its definitely wrong – downrep_nation Jun 9 '15 at 21:44

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