Initially, Herbert White has a playful, humorous attitude toward the monkey's paw. This is shown through Herbert's reaction when the sergeant-major tells the family about the fakir's spell, which gives three men three wishes:

“Well, why don’t you have three, sir?” said Herbert White, cleverly.

In addition, Herbert is the first one to suggest that the family use the monkey's paw to make three wishes. In fact, he believes that the monkey's paw can make the family "rich, and famous, and happy." For Herbert, the monkey's paw presents an opportunity for the family to change their fortunes. As a result, he suggests to his father that he make a wish for £200, to see if the paw really works.

Moreover, as he goes up to bed, he jokes with his father that the £200 will appear in his bed in the middle of the night. He further jokes that something evil will be sitting on the wardrobe watching his father. Herbert's attitude, is, therefore, very playful and not at all serious.

In an ironic twist, however, his father does receive the £200 that he wished for. It is Herbert's death in an accident at work which brings them the money.

Herbert's general attitude towards life is youthful, irreverent, playful, and optimistic. He is always joking, and he makes jokes after his father obtains the monkey's paw. When Mr. White voices his first wish, Herbert is at the piano.

As Herbert played a loud, dramatic chord the old man suddenly cried out in a trembling voice. His wife and son ran towards him.

Everything Herbert says about the monkey's paw shows disbelief and ridicule.

‘Well, I don’t see the money,’ said Herbert....And I am sure I never will.'

‘You’ll probably find the money in a big bag in the middle of your bed,’ Herbert joked as he said goodnight to them.

‘Don’t spend any of the money before I come back,’ Herbert said, going to the door.

All of Herbert's skepticism is intended to create the impression that the monkey's paw is a fake and that nothing at all is going to happen. The reader is in for a shock when he learns that it was the skeptical Herbert who made it possible for his father's first wish to come true. Herbert was killed in a factory accident and his company is paying the parents two hundred pounds as compensation, the same amount Mr. White wished for.

Herbert is presented as youthful, good-natured, and always joking, in order to suggest by contrast how empty and desolate the household seems without him. This tragedy and its aftermath of gloom are what prompt Mrs. White to insist on her husband using his second wish to bring Herbert back. But Herbert's fun-loving personality will also serve as a contrast to the living-dead Herbert who seems to be outside knocking at the door after White's second wish.