A&G is fabulous...plus they play really good music, not shopping music. Once I went & it was Italian opera, next time it was Dean Martin. Just makes the experience that much mo' better.
Within walking distance of Montrose & Central (BTW - Did you see? Toot's is no more! Demolished!) is Montrose Deli on Montrose at Long. It's a Polish Deli , but everything is fresh, very nice prices, and the people are nice. Can be crowded, tho.
Also, tell your friend about Portage Park pool for in the summer. Olympic size pool & also a high diving pool (3 stories up). Poratage Park is a gem. I hope your friend explores the neighborhood, we lived there for a few years & loved it. Nice architecture too.
I can't believe I ate the whole thing!