Wouldn't it be possible for him to text you pictures of what he thinks you might like, and you can tell him which ones to bring back? Unless you want it to be a surprise I guess. As for the other thing, I'm pretty sure it depends on the food. You wouldn't be able to bring back seeds or liquids, but you'd be able to bring snacks like chips, um crackers/biscuits, etc. I might be mistaken about the seeds thing though, it might not apply to everywhere. You can probably search these kinds of things online to get more reliable information lmao
http://www.oki-islandguide.com/specialfeatures/must-have-souvenirs-from-okinawa
I think you can pick some specialty items from there? I personally like the glassware and chura-tama because it's beautiful, and if you want to ask for snacks you can also ask the special flavored kit-kats that are sold only in that region.
A nice yukata or kimono for you
How about a wind chime made of glass, like the ones you often see in animes or mangas? The ones they have in Japan are so pretty, it's hard to get your hands on them anywhere else, they are also not too big or too heavy
Bunch of Kit Kats
My Dad will be in Japan for a business trip and I was wondering what you guys would suggest I ask for as a souvenir/birthday gift. It can't be anything anime/manga related and it has to be able to go on a plane. I was thinking a bento box or nice folding fan, but I don't want him to be stressed if there are too many different options. He will be flying in to Tokyo then to Okinawa if that makes a difference. Thanks in advance!
PS. Do you guys know if you are able to bring back any food at all from Japan to USA?