I think there is some software out there somewhere that will let you do this...however it is illegal to do it. itunes is set up so that you can only burn things onto CDs or transfer to iPods, or use it on your own computer. You aren't supposed to transfer from computer to computer.
That being said, although it is illegal to do so, you could burn it onto a DVD if you have a DVD burner and send it to them that way. Oh, and did I mention that it was illegal? Ha Ha...I just can't help it...I don't want to encourage the behavior.
itunes is set up so that you can only burn things onto CDs or transfer to iPods, or use it on your own computer. You aren't supposed to transfer from computer to computer.
that's not actually true. iTunes allows you a certain number (i think it's 5, but it might be 3) of "shares" to other computers. this way you can share songs, etc. with your friends (or if you have more than one computer)...my husband and i do this all the time with music we buy, so we can both have it, and it's perfectly legit. iTunes calls it "FairPlay versions."
i think you could send your friend the actual file...iTunes usually sticks your files in your My Music folder (within your My Documents), but you can verify where the actual file is by right-clicking on the file in your iTunes library, selecting "Get Info" and then going to the "Summary" tab. then at the bottom it will say "Where: C:\Documents and Settings\Owner\My Documents\My Music\iTunes..." etc. something like that. that's where you'd find the file to attach into an email. if you look at the little file icon, you might notice there's a padlock on the icon (if you've purchased the file through iTunes)...that means it's locked and "share protected." however, once your friends have the file, they can open it up in iTunes and click on it to play. it will prompt them to enter the account info (user id and password) of the purchaser (you)...you'll have to give them this info. (you can always make a temporary password and change it back after they've gotten the file unlocked). and viola, they should be able to play the file and it's perfectly legal and legitimate...only thing is you can only share with so many people.
hope that makes sense!
ETA: i have only used this technique for music files, but i would assume it's the same for videos, tv eps, etc. can't guarantee it though!