Does the letter ever lose any of its pain for Hester in The Scarlet Letter?
I don’t believe that the pain of the letter is ever lessened for Hester, but I do think she becomes accustomed to the pain, and so it doesn't seem quite as dramatic as when it was new to her. After she and Dimmesdale have determined to take Pearl and run away together, back to Europe, Hester is in town with her daughter for the public holiday. She thinks to herself, in regard to the other villagers,
"'Look your last on the scarlet letter and its wearer! [...] Yet a little while, and she will be beyond your reach! A few hours longer, and the deep mysterious ocean will quench and hide forever the symbol which ye have caused to burn upon her bosom!'"
The fact that Hester still conceives of the letter as something which burns, like a brand or hot iron, lends itself to the belief that it is still quite painful for her to wear it. Further, when she discussed the letter with Dimmesdale in the forest, she says that she "'must bear its torture yet a little longer'" until they are able to get away. In describing its effect on her as "torture," Hester makes it clear that the letter is still extremely painful to her.