Kenneth S. answered 05/22/17
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I considered REGULAR octagon ABCDEFGH. (This must be a regular octagon for problem to make sense.)
# of diagonals is 8C2 (pairings of vertices) - 8 (discounts sides) = 20.
The # of distinct pairs of diagonals is 20C2 = 20(19)/2 = 190.
I tabulated all diagonals and what other diagonal(s) are parallel thereto:
AC // HD, EG 3 pairs //
AD // EH
AE // BD, FH 3 pairs //
AF // BE
AG // CE, BF 3 pairs //
BD already listed
BE already listed
BF already listed
BG // CF
BH // DF
CE see above
CF see above
CG // BH, DF 3 pairs //
CH // DG
DF see above
DG see above
DH see above
EG see above
EH see above.
THE TOTAL # OF possible parallel pairs pairs is 17, unless there's an error in my accounting.
Therefore I say P(randomly selected pair of diagonals are parallel) is 17/190.