Thanks again to all for suggestions. here is what happened... he relaxed the restrictions a bit (maybe it helped to give early warning, and to say things like "it's made of the same stuff you already eat") :)
Monday - meet at Government Center, walking tour of back bay and south end, great weather for looking around, dinner is Ethiopian at Addis Red Sea, which for my money is heads above Asmara. Great room, good prices on wine, great service. Mostly a great room. How can you not like walking down into a cave for dinner where you sit on little stools and eat with your hands? He had chicken, I had 3 veggie options + beef. Walked to Chinatown ("scary"), ginger ice cream at Wei Wei was tasted but pronounced "too sweet". I finished mine. But I eat everything in sight.
Tuesday - he really likes beer, so we met at Copley Station and proceeded west to Anam Cara in Brookline.. another excellent room, Sox on the big screen and plenty of tables. Great service from a great server. I had a pressed roasted veggie burger and big ol' crunchy fries. he had breaded shrimp. Several beers. All in all an excellent if absolutely unhealthy meal, and probably his favorite of the week. I think it's the best beer bar for many miles in any direction. The big beer list with long descriptions gets newcomers' attention. And the kitchen does a great job too, though they don't currently have the 3-mushroom appetizer that won my heart last fall. I like restaurants that change their menus, except when the remove items that I like :)
Wednesday - met at Kendall, walked to The Helmand. he had chicken again. He likes chicken. At the last minute he switched to Mourgh Kabab (char-broiled) so he at least had some food that had been near flame :) and roasted veggies, great looking rice and spinach. Kaddo appetizer with beef ("beef and pumpkin together?") was also a big winner. I had Kourma Challow - lamb sauteed with veggies... Helmand never disappoints. The generous basket of bread and 3 sauces that come out first were a hit, as they are with everyone. Again, fairly-priced wines made it a nice meal. Nothing scary! Walking tour of MIT, Cambridge, Harvard.
All things considered, it was a successful triple-header.