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Reopening a lost DM
Have you dmed someone in the past, only to find yourself unable to find that person or their dms again? Don't worry, no dms have been lost, and you can easily get them back!
There are two ways you can locate the dm:
This way requires you to remember some unique word or message you've sent to the other person. It could be something like their name, some phrase, a part of some link, just anything which helps narrow them down.
Once you have your unique word/message, go to the Messages tab, enter it in the search bar, and hit Search. If everything went well, you should see messages with their username at the top:

You can now use the username to send them a friend request and reopen your dms this way.
If for some reason you can't or don't want to send them a friend request, you can right click the message and choose "Open dm":

This works best if you haven't dmed many people in the past, or remember the rough date of your first dm with the other person.
Go to the Direct Messages tab, and try to locate the person you think you're looking for. Once you've found a potential candidate, you will see their username and, in some cases, avatar:

You can now use the username to send them a friend request and reopen your dms this way.
If for some reason you can't or don't want to send them a friend request, you can click the "Open DM" button:

Due to Discord's anonymization, in order to reopen dms with a deleted user, you will have to use the "Fetch info" option beforehand.
For Messages tab, this option is located under the right-click menu:

For Direct Messages tab, this option is located on the right side:

After using "Fetch info", you will be able to use the "Open dm" option like normal.