iTunes won’t send

They've checked the spam folder as well as the inbox on the email account ? Have you tried seeing if you can resend it : Resend App Store & iTunes Gifts - Apple Support ? If you can't : http://www.apple.com/support/itunes/ww (click on your country's flag, the country where you live, and which is therefore the country on the account ; click on Contact Support towards the top right ; click on Get Help under 'Talk To Us’)

You've contacted iTunes Support ?

See my first reply.

They should reply within 48 hours, if they don't contact them again

If you mean for where you are sending the gift no, it just has to be an email account that they have access to so that they can get the email

That doesn't matter, he just needs access to the email account

If he's checked the spam folder as well as the inbox, and if it's now been more than 48 hours since you contacted iTunes Support, contact them again.