This was a great place for italian seafood dishes. It was a very romantic restaurant. However, I do remember two guys who were playing instruments and singing shaking me down for some bucks in front of my date. It was a first date and I was trying to impress this girl. Now it just seems funny. This place must have closed in the late 80s. Too bad.
Fricano's, boy does that bring back memories, all pleasant. Fricano's and Yan-a-se on State street were 'our' places when my wife and I dated.
For expertly grilled squid and/or octopus I would recommend, as did Bryan, Santorini. Santorini uses lump (pure wood) charcoal and their grilled items, including lamb chops, are very good.
Yan-a-se also had a charcoal grill and one of their weekly specials was grilled baby octopus, which was a favorite. Katsu, who was the head chef at Yan-ne-se, owns Katsu on Peterson, which is one of, if not the, best Japanese restaurants in Chicago. I'll link to a post by Mike G on Kastu, if anything Mike is restrained in his praise.