What does ''grow a pair'' mean exactly? Is it offensive? Does it bring a man to a level of a girl/woman? Is it more offensive when a woman says it?
Thank you for the answers, especially from women. :)
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It is definitely offensive, as it means the man that is addressed should grow a pair of testicles, implying that he lacks masculinity at the moment this "advice" is offered.
How offensive it is depends entirely on the situation, of course. Between friends, it might not be perceived as offensive at all ("come on, we all did that jump. Grow a pair and jump!")
However, I would never use this to a stranger!
Depending on the cultural environment, this insult may indeed carry more impact when said by a woman, as in some cultures masculinity is very highly valued (e.g. machismo) and a male can be much more offended when a woman questions his masculinity than when a man does the same.
As others have already clarified, this phrase conveys the opinion that the person to whom it is directed is lacking in testicular fortitude. In my experience, this phrase can be said by anyone, to anyone, regardless of the gender of the speaker or the recipient.
Generally speaking (clearly there are no absolutes), it is offensive to male recipients because of the implicit questioning of their courage as a specific expected quality of masculinity; conversely it is offensive to both female recipients and any female who hears it because it perpetuates the idea that courage is a male trait and that the solution to lacking bravery is to be more like a man - to literally develop male genitalia.
Personally it resides within the group of phrases I'm perfectly comfortable using with people whom I trust - I walk a fairly blunt line with friends - but I would certainly think twice before using it with a stranger. In its literal sense it is both demeaning and misogynistic, but even colloquially it is rather offensive.