The paradox of hedonism, also called the pleasure paradox, refers to the practical difficulties encountered in the pursuit of pleasure. For the hedonist, constant pleasure-seeking may not yield the most actual pleasure or happiness in the long term when consciously pursuing pleasure interferes with experiencing it.

The term "paradox of hedonism" was coined by utilitarian philosopher Henry Sidgwick in The Methods of Ethics. Variations appear in the realms of philosophy, psychology, and economics.

Failing to attain pleasures while deliberately seeking them has been variously described:

But I now thought that this end [one's happiness] was only to be attained by not making it the direct end. Those only are happy (I thought) who have their minds fixed on some object other than their own happiness[...] Aiming thus at something else, they find happiness along the way[...] Ask yourself whether you are happy, and you cease to be so.

— John Stuart Mill, Autobiography (1909)

Happiness cannot be pursued; it must ensue, and it only does so as the unintended side effect of one's personal dedication to a cause greater than oneself or as the by-product of one's surrender to a person other than oneself. The more a man tries to demonstrate his sexual potency or a woman her ability to experience orgasm, the less they are able to succeed. Pleasure is, and must remain, a side-effect or by-product, and is destroyed and spoiled to the degree to which it is made a goal in itself.

— Viktor Frankl, Man's Search for Meaning

Happiness is like a cat, if you try to coax it or call it, it will avoid you; it will never come. But if you pay no attention to it and go about your business, you'll find it rubbing against your legs and jumping into your lap.