First, be sure you are correct and that it is a genuine flaw (not merely something that irritates YOU). You risk the obvious, being told, WELL YOU AREN’T SO PERFECT, EITHER, YA KNOW! Or worse, the friendship might be in jeopardy. It really depends on the seriousness of the issue, whether or not it is fixable (you don’t like her taste in clothing??? Big deal! You don’t like her taste in shidduchim – that’s another story), or whether the criticism is worth the potential backlash.
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