Dobby had been accepted to work in the kitchens of Hogwarts School of Witchcraft and Wizardry. He was ecstatic at the prospect of seeing his hero, Harry Potter, once again.
Dobby was a house elf, not old, not young, but in the prime of his life. He had tried to save Harry Potter's life from his previous owners' treachery. But Harry Potter prevailed. Dobby was very happy in the kitchens, but he was failing in cheering his friend, a fellow free elf, Winky, who had been set free, but was ashamed.
Dobby couldn't understand why she was not happy with the situation. She should be proud to be free in his mind. But, Winky continued to be upset. She was so sad, she started drinking the school's supply of butterbeer in startling amounts. Her master, Mr. Bartimus Crouch, was ashamed of her for a crime she did not commit. She was devastated to the point of heavy depression. Dobby thought a new job would cheer her, but he had been wrong. Having this new job seemed to upset her further.
No matter what he tried, Winky seemed to sink ever deeper into the depths of despair.
The night Harry Potter came to the kitchens, he and his friends tried to cheer her. But she would hear nothing of it. She wept even harder. Of her unkempt appearance, she was not ashamed. Her soup splattered dress was ruined, and her beret was filthy. She proved to be even more pitiful.
Dobby was cheered by the visit from his friend, and apologized for Winky. He proved his freedom, by saying something negative about the Malfoy's, but immediately felt guilty and tried to hurt himself. But Harry Potter wouldn't allow him. Harry Potter, his dearest, most treasured friend. Dobby could have hugged Harry Potter, but refrained from doing so.
Dobby liked Miss Hermione, and appreciated her efforts to show the other elves how much better it would be to be free. He stood by her, and tried to help prove her case, but the other elves soon grew angry and ignored the speech.
Harry and his friends left, but Dobby knew that he would be back, and then they could cheer Winky then. Harry Potter could do anything.