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 I am just wondering what is the best way to handle a large stack of DM messages to a friend list that should not be made public. do we giftwrap all of them or pick a select relay that is app specific for this stack of DMs?

the "right way" to do things on nostr feels like its moving and changing constantly so I am just asking 
 I'm not familiar enough with the DM chat NIPs to answer this with any confidence. @Vitor Pamplona and @hodlbod and @fiatjaf all know more than me about multi-party DM. 
 I don't know if I follow? Can't you just send each as a separate event? 
 You could but if a big stack of DMs goes to a large relay they can rate limit or block, as it can look like spam. 

cc: npub1ymt2j3n8tesrlr0yhaheem6yyqmmwrr7actslurw6annls6vnrcslapxnz 
 Just pick 2+ relays for your kind 10050 relay list and you should be good. Local backups are a good extra measure, either on a local relay or using a jsonl file.