I'll pencil you in 

A phrase meaning that the speaker intends to add the listener to a list, or make an appointment for the listener to attend a meeting at a later time.

(Pencil, a noun, is being used as a verb for the action associated with it.)

Fred: I need help with my homework.
Daphne: I'm not free until 6.30. I'll pencil you in for then if that's OK.
Fred: It's a date.

I'll pencil you in by phantom oddity May 20, 2004

I'll pencil you in 

To make definite plans to meet with someone. As in writing your name in an appointment book.

I'm free Thursday afternoon, so I'll pencil you in.

I'll pencil you in by jafo May 19, 2004

Break a pencil off in him 

To stab one in the neck with a n02pencil. Namely a prisoner.

We need to break a pencil off in him. Pedos mainly.

Break a pencil off in him by PanPizzaTheFurry March 11, 2022

I'll pencil you in 

To sexually assult/stimulate someone with a pencil, usually rubber end first for safety.

Oi, come here you silly slag... I'll pencil you in!

I'll pencil you in by Horny B April 27, 2008

I'll pencil you in 

It literally means that someone will give you the details of something, but is usually just someone trying to give you the runaround.

"What happened with you and your girlfriend?"
"I'll pencil you in later."

I'll pencil you in by Jessica May 20, 2004

pencil me in

Add me to your calendar with a soft maybe.

Means that you make plans to chizillax wit me but that shiz aint fo sho.

Implies flexibility of plans.

This comes from a time when calendars were a written thing - you could schedule it in pen meaning you cant change it, cast it in stone meaning 100% its on, or be wishy washy and pencil it in so you could erase and change it if need be.

can be used as n expression of flexibility:

Tom: Want to smoke a blunt with me Saturday night?

Dick: I’ll be home after work

Tom: pencil me in for seven.

Dick FO SHO, U gonna SMD?

Tom: Nah

Pencil me in for 7 o’clock I may be a little bit late

pencil me in by NYCGAY March 5, 2022

who pissed in your pencil case 

Something you would say to someone who is being rude or is in a shitty mood.

similar to who shit in your cereal.

Pat: Hi bill
Bill: Fuck off
Pat: Who pissed in your pencil case!

who pissed in your pencil case by Crocodoodle666 May 17, 2016