Making money "the hard way" usualy means via anal or rough sex.

Someone people turn to when they're sad who makes them feel better.

In Craps making a hard way bet means going for the total of the two dice on doubles. Say you wanted to go for a hard six, the only way to do it is with two threes. It is called the hard way because it is not easy to hit. There are only four hard way combinations: hard 4 (2x2), hard 6 (3x3), hard 8 (4x4), and hard 10 (5x5).