Self-deprecation results from low self-esteem. The way I would deal with it is to tell the person those aspects of their personality that you enjoy, (always start with a positive). Then bring the person’s attention to their self-depreciating behavior and let them know that the end result is that this behavior makes you feel ‘x’ and for that reason you are finding it hard to spend much time with them. After you tell them that, you make it known that you would find it much more fun and interesting to be with them if they would knock off the self-deprecation. If the person finds that impossible to do, then perhaps it is time for them to get some professional help to help them feel better about themselves. This is something they deserve, so something they should endeavor to do to get rid of this aggravating aspect of their personality. It is merely a suggestion you are giving because you care about them. However, you are making it known that you are not a mental health professional, so it is best for them to work with one because they have the skill set to really help them build up their self-esteem letting go of this annoying behavior.
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