Charlie: Let me tell you something about feelings. Feelings are like your mother's breasts. You know where they are, but they're best left unfelt. Rose: It's an interesting analogy, but may I point out that a mother's breasts are a source for nourishment and comfort? Charlie: Yeah, well, my mother's breasts were a source of silicone and Russian vodka. (“Who’s Vod Kanockers”)
Charlie will do anything not to feel his emotions and he learned this lifestyle from his mother who also drowns her emotions in drunken sex with random people. Alan eventually convinces Charlie to sober up and let his emotions out, but soon after, he is back to his old lifestyle and drinks his feelings away.
Because Charlie spends so much of his money on gambling, drinking, and impressing girls, he does not spend any of his fortunes on anyone