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It's alright. I've never known a Bess so for me, my thoughts are probably almost entirely word-associative. Best, boss. It's adult-ish for me, not sweet or youthful, because "old-fashioned" and no longer a natural nickname.
Positive traits I could easily picture belonging to someone named Bess: qualified, shrewd, competent, ambitious, fit
Negative traits I could picture easily: insensitive, sarcastic, ruthless, imperious, impatient
I like this image alright, but the sound of the name doesn't appeal to me very much.

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- mirfak