Summarize how Douglass learns to read and write, and then explain why, Douglass finds himself "regretting" his own existence at this point in his life.
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While living at Master Hugh's for about seven years, Douglass learned to write. His plan to learn to read centered on making friends with the poor white children of Baltimore and learning from them a little at a time. He used to complete his errands for Mr. and Mrs. Auld quickly, and then meet up with his new friends. He often used to give them bread (as he was actually better off than most of them) for lessons. The fact that he was a slave moved his young friends.
Now twelve, he began to chafe under the thought that he would be a slave for life. It was about this time that he got hold of the Columbian Orator, a book that dealt with the relationship of master and slave and demonstrated how slavery made no rational sense. In this book existed a speech by Sheridan on behalf of Catholic emancipation, which was a "bold denunciation of slavery, and a powerful vindication of human rights."
What became clear to Douglass was that his master was right – learning did make slaves intractable and unmanageable. He came to perceive slaveholders as no more than "a band of successful robbers" who had gone to Africa and stolen them from their homes. He felt discontentment surge through him and often wondered if learning to read had been more of a curse than a blessing. His enslavement tormented him unceasingly. Sometimes Douglass wondered if he should kill himself or do something which would get him killed, but he continually hoped that one day he might attain freedom.