Literary Advice: Ask Dean Moriarty

Last week we kicked off our literary advice column with Miss Havisham, the lady of the manor featured in Charles Dickens’ novel, Great Expectations. This week Dean Moriarty from On the Road has answered your questions with aplomb. Next week it’s Howard Roark from Ayn Rand’s libertarian screed, The Fountainhead, so feel free to ask him questions in the comments section below — just make sure you’re deferential, but not obsequious. You know how that enigmatic architect feels about weakness.

Dear Dean,

You are a child of the rainbow who bears his torment in your agonized priapus. You are Oedipus Eddie, scraping bubble gum off of windowpanes. What do you have to say for yourself?

Sincerely,

Carlo

Dear Carlo,

Everything’s straight. I’m going to divorce Marylou and marry Camille and go live with her in San Francisco. But this is only after you and I, dear Carlo, go to Texas, dig Old Bull Lee, that gone cat I’ve never met and you’ve told me so much about, and then I’ll go to San Fran. How’s that sound? In the meantime, we have to stop the machine and just sleep, though I don’t mean to bring my peremptory tone to bear in regard to what you’ve just written, I just absolutely, simply, purely and without any whatevers have to sleep now. Goodnight.

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Dear Dean,

What’s this I hear about you sleeping with three girls at the same time? How do I get in on that?

Sincerely,
Major

Dear Major,

Oh yes, oh yes, that’s the way it goes. If you’d like to start with a threesome: you, me, and Marylou, then you’ll have to wait in line because Sal is next.

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Dear Dean,

I’m desperate and unemployed in New York but was thinking of moving to San Francisco for a job. Do you have any advice on if I should stick it out and try to stay here or if I should give it all up and move across the country without any guarantees?

Sincerely,

Stuck in the Middle

Dear Stuckster,

Oh I could tell you stories about that frosty fagtown New York and extol the virtues of that golden land in San Francisco, but dammit, look here, we must admit that everything is fine and that there’s no need in the world to worry, and in fact we should realize what it would mean to us to UNDERSTAND that we’re not REALLY worried about ANYTHING in the end. The only thing you should be concerned about is finding true relaxation and knowledge.

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Dear Dean,

I’ve been having a few problems with my old man and was wondering if he ever gave you any trouble.

Sincerely,

Precocious Preteen

Dear PP,

One time I rode a freight from New Mexico clear to LA — I was eleven years old, lost my father at a siding, we were all in a hobo jungle, I was with a man called Big Red, my father was out drunk in a boxcar — it started to roll — Big Red and I missed it — I didn’t see my father for months. I rode a long freight all the way to California, really flying, first-class freight, a dessert Zipper. All the way I rode over the couplings — you can imagine how dangerous, I was only a kid, I didn’t know — clutching a loaf of bread under one arm and the other hooked around the break bar. This is no story, this is true, but don’t worry about your old man, kid, because you’re going to be just fine.