Learn English – What does “why yes” mean

The answer to Part 1 of your question is It depends

It depends on:

• The age of the woman to whom you are speaking (don't, if she is over 25)

  Your age relative to her age (should be about the same, and it is OK if you are obviously senile)

  The sense of humor of the woman (it should be earthy and robust)

  How much you care about your relationship with the woman (if you care, be careful)

  Whether there are other people around (If she feels she has to fake being a good sport, you are dead)

Never say anything like that if you are in a position to influence her career.

There is nothing to be gained by such a remark, and much to be lost. It is not a mere extension of addressing a group of men and women as "you guys".

Think of the reverse: How would it strike you if a woman told a chubby man that he should wear a bra? (Not an exact analogy, but close enough.)

Line is a line of descendents, and "run high" is an idiom based on a river "running high," meaning with more water than usual (i.e. a higher, and probably more dangerous water line). It's much more typically used for intense emotions (as in the phrase "tempers were running high at the Iowa caucus") but in this case it means an overabundance of daughters --more, perhaps, than Simon (or his descendents) would have voluntarily chosen.