Can I transfer videos from iTunes to an iPad not associated with it? I've got some (non-DRM) videos in iTunes that I'd like to transfer to my wife's iPad. She bought the iPad and set it up without ever connecting it to a computer, so it's never been synched with iTunes anywhere.

When I plug the iPad into my laptop, I'm asked if I want to register. When I click Register Later, I see this:



I'm concerned that selecting Set up as a new iPad will wipe out my wife's settings and / or content. Can I select that option safely, or is there some other way of getting my videos onto her iPad?

Update: I should note that I can't simply drag video files to the iPad in the iTunes sidebar. The iPad shows up like this:



Right clicking on the iPad in the sidebar produces only two options: "Eject iPad" or "Restore from backup". No option to Transfer Purchases, though the iPad and Mac are both configured to use the same Apple ID for the iTunes Store.

I assume I should be looking for the iPad to show up, as an iPhone does, with a list of media types underneath it so that I can view / drag things to its library.

I've also confirmed I can't drag video downloaded from the iTunes Store, either, so it's probably not a format conflict.
New set up will wipe out everything.

You can plug iPad into her iTunes and mark the option "Manually manage music and videos", save (sync), then plug again on your computer.

If you are careful when cross connecting, you can prevent cross-syncing the same information from two computers for this iPad, but still have each computer take care of part of the sync "situation".

other option is:
Copy the videos to her iTunes, then add them to her iPad from there.

Last option:
- Backup all the app data, videos, music and even pdf files with third party software (TouchCopy, iExplorer, PhoneToMac or any other you like). Do not backup system files.
- Set up the iPad.
- Copy everything back using the same third party software.