Of course you can gift YOLO, but at this point, it is by the issue, not by the year. And if you want to do a back issue along with a new issue, you'll have to do that in two different windows. Unfortunately we aren't able to send along a message to the person you're gifting it to. We're working out the kinks on that, and on the back issue scenario, and the annual subscription, but for now, make sure you let your friend know that there's a YOLO treat on its way.