Or what about auto generating a new npub for the DM, then destroying when DM chat deleted.
1) new npub spun up
2) only each others personal relay (self-hosted, Citrine) is shared with new npub with friend, or immediately be in DM with friend, who also has a new npub [messaging "connected"]
3) "connected" message could be signature from original npub; verifible confirmation it's them
4) chat encrypted and pseudonymously
5) when chat is deleted, auto delete npub and contents on relay (be cool to spin up and destroy relays quickly)
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That was our initial idea, but we realized most of the time you don't really know the person you are DMing with. Trusting them (and their relays) with the new npub (and the possibility of linking all your keys together) seems like a non starter.

GitHub
Adds key aliases to NIP-17 by vitorpamplona · Pull Request #1306 · nostr-protocol/nips
A simple way to:
Remove the final metadata leak from NIP-17 (the public key of the receiver is on the gift wrap)
Distribute a stream of messages t...
Doesn't @0xchat use this? How do they get past these problems
Give me the TLDR on 'MLS based messaging lands.'?