Whenever I try to bounty hunt players I just feel bad about trying to take their bounty and I chicken out. How can I get over this?
lose your sanity
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just dont bounty hunt players. if you want fame go farm architect Merlot or just bounty hunt npcs.
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Trash talk so they get mad at you first lol
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Become a true warrior.
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Also, just don’t talk with them if you don’t wanna get connected. Silently approach and murder them while they least expect it.
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So your a psychopath? Personally i prefer the sociopath approach
That’s not really what I do for bounties.
First, I ask them to 1v1.
If they say no, I kill them anyway.
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Lawful evil
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abandon your humanity
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dont bounty hunt players then
stay sane
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just rush them, dont think just act
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I have the same issue. I ask them to meet me in Munera Garden and let them finish anything they need to deal with first.
Didn’t work out so well when I tried bounty-hunting a Navy Captain who stood at Silverhold the whole time.
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play deepwoken for long enough and you won’t care
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Did I just catch you being compassionate? Think about it this way, 9 times out of 10 they won’t feel sorry about taking your bounty. It’s either kill or be killed in these wild parts! 
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just use my simple approach bro
step 1: go up to target
step 2: violently beat them up without saying a word
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Act like they npc and ignore all angry messages in inbox afterwards (If you get them, of course)
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use social media for 20 minutes and by then you’ll lose all faith in humanity 
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Unbind yourself from the shackles of humanity. Descend into the depths of RKing.
SHOW NO MERCY GRAHHHH.
WALK THE PATH OF THE DAMNED, DESTROY ALL IN THE NAME OF GLORY, BE THE BEST BE THE KING BE THE ELITE!! ENDLESS ONSLAUGHT!!
(just silently murder them and if they trash talk just ignore or talk back if you want to lol, if they start to whine about it tell them to leave or sum)