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I'll pencil you in 

This is what a person says when he is making a tentative appointment.

"I'll Pencil" (because the appointment can be erased) "you in" (to my schedule book).
Ozzy: Hey, can I come up to your big fancy office and make fun of you?
Boohiss: Er. I'm kinda busy this week. Tell you what, I'll pencil you in for 4:30 on Thursday.

i'll lightly pencil you in 

To pencil someone into a schedule but using a light amount of pressure. This way, as you know they will always cancel, when you erase, there is no visual indent of their name in your schedule.
Guy: sorry I keep cancelling on you, would you like to go to the cinema on Friday?

Girl: yes, I'll lightly pencil you in.
Guy cancels
Girl to friend: I am glad I only lightly penciled him in, as there is no indent to remind me that he cancelled AGAIN!

I'll pencil you in 

When somebody wants to schedule something with you, but you don't want to use a pen to finalize it in your calendar because that person is a loser. If something better comes along -- you can erase it.
Sure, I'd love to watch slides from your trip to the Grand Canyon -- I'll pencil you in.
I'll pencil you in by Kid May 20, 2004

I'll pencil you in 

tenatively allocate time to meet, see, or conversate
We should get together. I'll pencil you in for 6:00.

I'll pencil you in 

A nice way to say "fuck off...im not interested"
Girl: Want to go out friday night? I'll bring pictures of my horse!
Guy: ...Um....I'll Pencil You In.

I'll pencil you in 

To schedule someone for a meeting.
To enter an appointment into an appointment book with pencil.