Our expert says:
Indeed, it is puzzling why somone would choose to remain friends with someone such as you describe. Its not being "non-judgemental" to keep foolishly forgiving someone who keeps on doing bad things - that only encourages them to remain bad. Being judgemental has its place. When a pickpocket is running away with your bag, and you shout "Stop Thief!" he cant turn to you and say "Stop Being Judgemental!"
Maybe instead of directly challenging your bf to ignore this "friend", it'd be more useful to calmly chat with him about his experiences with this guy over the years, whether he sees what you find objectionable about the guy, why he seems reluctant to criticize him or let go of him. That would help you to make a more informed decision about what to do about it
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