We study the dual of Philo's shortest line segment problem which asks to find the optimal line segments passing through two given points, with a common endpoint, and with the other endpoints on a given line. The provided solution uses multivariable calculus and geometry methods. Interesting connections with the angle bisector of the triangle are explored. A generalization of the problem using $L_p$ ($p\ge 1$) norm is proposed. Particular case $p=\infty$ is studied. Interesting case $p=2$ is proposed as an open problem and related property of a symedian of a triangle is conjectured.

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