In high traffic multilanguage areas world wide it's not uncommon to meet people who speak 5+ languages.
Any way, I don't expect Japan to be English friendly, there's some districts that are pretty safe bets, and there's a decent amount of written English around in the big cities (global tourism's big, and printing twice, once in Japanese, one in English is a cost effective way to cover a wide base). I'm studying Japanese pretty hard when I'm not working on school and my brother's Japanese is getting pretty decent. From what my expat friends say if you can get the subject, verb, and a "please" or "excuse me" out you can get just about anything or go any where without trouble.
I have my official itinerary if any one's curious, complete with some of my travel notes XD
May 18 - 22nd Tokyo
May 23 - O'dark Hundred departure for Hiroshima and Miyajima,spend the night in Hiroshima, tube hotel?
May 24: Early departure for Osaka, Osaka castle, wander Osaka, evening departure for Kyoto
Evening May 24 - May 26 Kyoto, stay in Ryokan, evening departure for Hakone mountain region around Lake Ashino. It can easily be reached from Tokyo on the Odakyu line for Onsen episode.*/**
26-28 May Onsen, late morning return to Tokyo on the 28th
28th - June 1st Tokyo
June 2nd - Evening departure back to the states, big lunch to celebrate the end of trip?
*VITAL: Ensure that the Ryokan, and the Onsen accept guests with some tattoos. Do this prior to making reservations.
**Stuff to do on the Onsen day: There is a castle at Odawara near Hakone, and boat trips and mountain walking and cable cars, etc. Several nice museums including a museum of toys and an outdoor sculpture museum