They are both characters that are in love with a person that they cannot openly admit this to. They both ponder and wonder whether or not they dare to tell her. And indeed there will be a time to wonder, "Do I dare?" and "Do I dare?" (Eliot 666). Neither of them could bear the thought of her not returning their love so they hide it and keep it quiet. Though Gatsby does end up admitting his feelings for her, he spends each year after he met her thinking about her, and then months across the bay from her, creating images of telling her. They both have set their minds to view themselves as not good enough for her, therefore leading to masking themselves.
Neither Gatsby or Prufrock think that who they truly are will be enough, so they wear a mask of lies so that she might not see who they truthfully are. There will be a time, a time to prepare a face to meet all the faces that you meet (Elliot 664). Though Prufrock never actually musters up the nerve to talk to her and he never got a chance to tell her, he expressed wearing a mask in public in case he did see her and in his poem he expressed the feeling that everyone does hide themselves in certain situations.
In conclusion, they are very different people but similar in many of their personality traits, especially questioning "Do I dare?" and the way they both wear masks. Works Cited
Fitzgerald F, Scott. The Great Gatsby. New York; Simon & Schuster, revised 1992.
Eliot, T.S. "The Love Song of J. Alfred Prufrock." Elements of Literature" 5th course, 2003.