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I'm riding that train, reading that book. . . 

An expression which originated during a drunken late-nite discussion of the origins of expressions. It means, "I see what you're saying, where you're going with that."
Drunk person A: "Dude, you know what I mean?!"

Drunk person B: "Totally, Dude. I'm riding that train, reading that book."

I'm riding that train, reading that book. . . 

Same as saying, "I feel you."
Cool Person A: "So then, I told the guy that there was no way I would ever consider his lame-ass job, you know?"

Cooler Person B: "Yeah, man. I'm riding that train, reading that book. . ."

riding the train 

To be "riding the train" means to be single and in pursuit of someone to spend the day and/or night, without the intent of perusing a relationship with that person.

On Valentine's Day the only way to "get off the train" would be to find a date, to give up in the pursuit of finding a date or when the clock strikes midnight and you're all alone.

Related: To be on the train / To be on the desperation train / To be on the train of despair.
- What are your plans for V-day?
- I'm riding the train this year.
- No worries dude, you'll be off the train way before V-day.
riding the train by a66spam February 1, 2014

riding the train 

when your dog or cat, after a particularly difficult bowel movement, decides to sit on the floor, and pull it self forward using its front feet only, dragging it's asshole on the (usually) carpet to scratch the ham hocks (hemmies) off, then gets up, turns around, and sniffs the skid mark
"OMG, look, Coby's had the hershey squirts, came right inside and started riding the train."

Riding the gravy train

Riding the gravy train is the name of the game. (not to be confused with The Game)
In this context, the game being the life lived by the people in the "industry" with their soulless addiction to pointless materialistic advantages such as money and fame.
So basically if you're "riding the gravy train" you have sold your true self out to the music industry/any other type of corrupt medium for said perks.
Roger Waters in a critical song "Have a cigar" by Pink Floyd :

Come in here dear boy have a cigar you're gonna go far,
You're gonna fly high, you're never gonna die,
You're gonna make it if you try, they're gonna love you.

Well I've always had a deep respect and I mean that most sincerely,
The band is just fantastic that is really what I think,
Oh by the way, which one's Pink?

And did we tell you the name of the game, boy?
We call it "Riding the gravy train".
Riding the gravy train by lisartsy November 2, 2014

Riding the Midnight Train to Slab City 

Used to delicately explain that someone has died.
"Hey, man, sorry to hear your mom is riding the midnight train to slab city."