Reading Guides: On The Road by Jack Kerouac

Each month I’ll be posting points discussed at the my book club for those who are curious about what we talk about ( including points made prior, but not discussed) or need a reading guide for the book for their own clubs. You’ll find a list of all reading guides on the reading guides page. You’re welcome to use it and to adapt the questions to your own social group use, but if you do and have a website or blog please link back using one of these badges.

August’s book was On The Road by Jack Kerouac. It was funny because no one actually finished it except myself (that cracks me up) so were able to discuss it in parts, but not as a whole. We’ll be discussing it on the book club’s Facebook group, but in the meantime I’ll still be posting the points that I was going to use as our guide for the meet up.

Dean and Sal

  • Did Dean have any good points in being a role model? Or was Dean just a bad influence all round?
  • Does anyone think that Sal would have had just as much urge to travel as he did without Dean’s influence?
  • Do you think the same for the rest of his friends? What role do you think they played in his need to move?
  • How do you think Sal reacts to Dean’s obsession with women and sex? Do you think he looks upon it with jealousy, envy, admiration, or something else?
  • Do you think Dean’s behaviour with relationships influences Sal’s given how much Sal looks up to him or do you think Sal does find his own way?
  • What role do you think women play in Sal and Dean’s relationship?
  • What do you think of their behaviour and reactions to the situation with Marylou? And how do you think Marylou and her behaviour influenced Dean and Sal’s?
  • In the beginning Sal doesn’t seem to know how he feels about Dean even though he seems to be drawn to him. Do you think this resolves itself by the end of the book or do you think Sal never understands how he feels?


  • What was your impression of Sal? Did you find him naïve and easily lead, or did you find him strong willed and hard to influence, something else? Did this change throughout the story?
  • Do you think Sal learned anything by the end of his journey? What do you think it was and how did this come across?
  • Why do you think Sal never mentions Terry’s surname?
  • What are your impression of Sal’s relationship with Terry and his leaving? What do you feel influenced his decision?


  • What do you feel helped contribute to Dean’s manic and frenetic character going by what you know of his background? Do you think his environment would have played a part in it or do you think that doesn’t matter?
  • Do you think Dean’s manic state was influenced socially, was generational, or something else?
  • Given Dean’s character and his manic episodes, do you feel that Dean should be given more leeway? Would you find yourself excusing his actions? Do you feel Sal does?
  • When Dean can’t seem to function anymore at the end, what do you think this means for Dean? Why do you think he has become like this?
  • Did Dean incite sympathy, dislike, or something else while reading and did you find that changed throughout the story?


  • Jack Kerouac wrote this in one sitting, what do you think are the pros and cons of him writing in this way?
  • Do you think Kerouac’s writing is emotive, stunted, well rounded, or something else?
  • What are your impressions of his descriptions when it comes to the people and his travelling?

Other Points

  • Do you feel there is a moral lesson to this story? What stood out to you and why?
  • What have you taken away from reading On The Road?
  • Do you  have a favourite or favourite characters in this story? What do you like about them?
  • Who would be your least liked character and why?
  • Does your view of On The Road change with knowing this is not a fictional piece?
  • Did you find the tone changed when they went to Mexico? In what way do you feel it changed? Was it positive or negative?
  • Does anyone find that now they’ve read On The Road they want to look up the characters mentioned and their works?
  • Do you think their love and mention of Jazz is a proper portrayal of the beat generation or just a factor of the times?
  • Kerouac writes of a world where drugs, criminal activity, sex and violence are a glorified occurrence. Do you think Sal and Dean’s actions are wrong? Do you think Kerouac approves of their behaviour?

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