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pencil you in 

To tentatively make an appointment or commitment. Implies it could be changed or canceled, since pencil marks are erasable.
Bob: "I got tickets to Saturday's game. You want to go?"
Tom: "If I can. I might have to work that day, but I'll pencil you in."

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 

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.

I'll pencil you in 

Informal idiom meaning to make an appointment for someone; to "pencil them in" to the schedule.
"Can I see the doctor right away?"
"No, but I can pencil you in for a two o'clock appointment."