What are you guys kidding?!
Send him envelopes with LOTS of stickers and colors!
Send him boxes of cookies and other geedunk!
Do NOT send naked pictures, that would be bad. But the others are good. Yes, he'll have to pump out a few more pushups and yes he'll likely end up eating a bunch of cookies at once but it is FUNNY. It builds camaraderie with his fellow candidates. It provides a very good relief through humor. Getting pushed for stuff like that does not suck nearly as much as having to push for most other things. And really, when you laugh while you're pushing, it makes pushing for other reasons not as bad. I dunno why, but it works. He WILL laugh about it, maybe at a later date, but he will laugh.