My son's girlfriend gave him a silver cross on a slightly longer sturdier chain than usual. Needs to be hidden under t-shirt. That was pretty much the only thing they allowed him to keep. If this is an appropriate gift, find one that is one solid piece, not two pieces soldered together. Also, invest in a spare chain....you may need to send it to him later!
Collect all friends and family mailing addresses, phone numbers, and email addresses and put in a small/pocket sized address book. Mail this to him with your first letter.
Promise to mail him letters regularly. They do have a small corkboard that they can pin personal items, such as pics. Throughout Plebe Summer, GF sent small laminated pics of them together. Most were silly, happy pics that would give him a smile rather than a tug at the heart. Handwritten letters will be treasured, so keep them coming....and keep the positive!
Your best gift will be a great big smile and hug when he leaves. Let him know how proud you are of him and give him absolutely no reason to worry about you while he's going through the toughest summer that he's experienced...so far.
And..FYI...they are still together, the best of friends, and truly supportive of each other. This summer they will be trekking through China....If their relationship can survive Plebe year and a roughing it trip through China I think there is hope for them!