Well, the man who despises himself tries to gain self-esteem from sexual adventures — which can't be done, because sex is not the cause, but an effect and an expression of a man's sense of his own value.
The men who think that wealth comes from material resources and has no intellectual root or meaning, are the men who think—for the same reason—that sex is a physical capacity which functions independently of one's mind, choice or code of values. They think that your body creates a desire and makes a choice for you—just about in some such way as if iron ore transformed itself into railroad rails of its own volition. Love is blind, they say; sex is impervious to reason and mocks the power of all philosophers. But, in fact, a man's sexual choice is the result and the sum of his fundamental convictions. Tell me what a man finds sexually attractive and I will tell you his entire philosophy of life. Show me the woman he sleeps with and I will tell you his valuation of himself.
No matter what corruption he's taught about the virtue of selflessness, sex is the most profoundly selfish of all acts, an act which he cannot perform for any motive but his own enjoyment—just try to think of performing it in a spirit of selfless charity!—an act which is not possible in self-abasement, only in self-exaltation, only in the confidence of being desired and being worthy of desire. It is an act that forces him to stand naked in spirit, as well as in body, and to accept his real ego as his standard of value. He will always be attracted to the woman who reflects his deepest vision of himself, the woman whose surrender permits him to experience—or to fake—a sense of self-esteem. The man who is proudly certain of his own value, will want the highest type of woman he can find, the woman he admires, the strongest, the hardest to conquer—because only the possession of a heroine will give him the sense of an achievement, not the possession of a brainless slut. He does not seek to gain his value, he seeks to express it. There is no conflict between the standards of his mind and the desires of his body. But the man who is convinced of his own worthlessness will be drawn to a woman he despises—because she will reflect his own secret self, she will release him from that objective reality in which he is a fraud, she will give him a momentary illusion of his own value and a momentary escape from the moral code that damns him.
Observe the ugly mess which most men make of their sex lives—and observe the mess of contradictions which they hold as their moral philosophy. One proceeds from the other. Love is our response to our highest values—and can be nothing else. Let a man corrupt his values and his view of existence, let him profess that love is not self-enjoyment but self-denial, that virtue consists, not of pride, but of pity or pain or weakness or sacrifice, that the noblest love is born, not of admiration, but of charity, not in response to values, but in response to flaws—and he will have cut himself in two. (..) His body will always follow the ultimate logic of his deepest convictions; if he believes that flaws are values, he has damned existence as evil and only the evil will attract him. He has damned himself and he will feel that depravity is all he is worthy of enjoying. He has equated virtue with pain and he will feel that vice is the only realm of pleasure. Then he will scream that his body has vicious desires of its own which his mind cannot conquer, that sex is sin, that true love is a pure emotion of the spirit. And then he will wonder why love brings him nothing but boredom, and sex—nothing but shame.
Ayn Rand, 1957, Atlas Shrugged