*Crunch crunch crunch* Mmmm... bones good. Love them.
It might be where you grew up. People who grew up on the coasts probably got used to some fish in their diets from childhood. My parents regularly had canned smoked fish in the house, and once I received Communion, Mom made salmon patties from canned salmon every Friday (way to be creative mom).
We also regularly ate shrimp, clams, and squid. And not deep fried, but usually sauteed. Clams went on top of pasta with a garlic sauce. Mussels were usually a holiday thing. And like the good (cough) Sicilian Catholics that we were, on Christmas Eve, there were no meat meals, so we ate a lot of fish. Even silly 1950s hors d'oeuvres like cream cheese and anchovies on crackers. In summer, Mom and Dad would go to the Cape and bring home lobsters, so not an every day treat.
Another vote for Wild Planet. They are so plump in comparison to sardines I've had from the grocery store. Cans are bpa free, which I think is important for an old lady (me). And honestly, the bones aren't like hard bones, they're just a little crunchy. They make one (and other brands do also) that are in lemon and olive oil, so that might be a nice introduction to them.
If you're squeamish re: sardines, I'm guessing sucking the heads of crawfish would be out? Just kidding - I can't get past my ick factor and eat turtle soup, even though I'm a five block walk from a restaurant that prides itself in its turtle soup. It's not the turtle, it's ripping the shell off that gives me nightmares. *whimper*
"Right is right, even if no one is doing it; wrong is wrong, even if everyone is doing it." - St. Augustine