If you like challenging literature, you should take on the most challenging book in the English language, Ulysses by James Joyce. Don't be afraid! You can do it! I challenged myself to read it in a year. But I quickly became engrossed in the complexity, and I finished in a month. You can too. Ulysses tells the story of a day in the life (June 16, 1904 to be exact) of Harold Bloom and Stephen Dedalus, an advertising agent and artist respectively, as events take them through the city of Dublin, leading them to contemplate their place in the world, examine their own humanity, and make decisions about the kind of life they want. It's a story anyone who has ever felt like an outsider can relate to. The plot is brilliantly constructed around the story of Homer's Odyssey but told completely through the eyes and in the minds of its main characters. A groundbreaking book when it was published in 1922, it's still worth the effort! I recommend the Gabler edition for ease of reading, and as a bonus, check out the New Bloomsday Book by Harry Blamires for help with the plot and allusions.
Corrects and restores many missing portions of Joyce's controversial and influential novel about love and marriage