Do I need to plug in my apple pencil every time I want to use it?

Hello Roachcook,

Welcome to Apple Support Communities!

We can help you get the most from your Apple Pencil.

We see you viewed the Apple Support page for Pair Apple Pencil with your iPad - Apple Support

This section from the Apple Support page has the best answer to your question:

"Pair your Apple Pencil (1st generation) with your iPad (10th generation)

Remove the cap and plug your Apple Pencil and a USB-C cable into the USB-C to Apple Pencil Adapter. Plug the other end of the cable into your iPad.

When the Pair button appears, tap it. Wait for your Apple Pencil to pair, then unplug it from the USB-C to Apple Pencil Adapter.

Your Apple Pencil and iPad stay paired until you restart your iPad or pair your Apple Pencil with another iPad. When you’re ready to use your Apple Pencil again, use the same steps to pair it with your iPad"

So you won't have to pair it again unless you restart the iPad or pair with another iPad.

We hope this helps to answer your question about how often you'll need to pair them.

Cheers!

You will not need to re-pair the Pencil with your iPad after a simple restart. An iPad that is idle will simply “sleep” in its low-power state; in this state, the iPad doesn’t fully power-off.

However, if you fully shut-down (i.e., turn off) the iPad, it will be necessary to again pair the Apple Pencil with your iPad10 using the charging cable.