I have fond memories of the Old Spaghetti Factory. All of the machinery and wide spaces always left me with a sense of wonder, when I was tiny. It's still a nice place, though I understand it's not all that it used to be. Other family friendly Gaslamp restaurants include the Chopahn Authentic Afghan Cuisine and Spike Africa's, but I'll always have a soft spot for the Factory.
La Jolla Cove for a romantic evening, La Jolla Shores for something more fun. It's really that simple: there's absolutely no competition, whatsoever. The only other beach that can compare is The Strand on Coronado, and that's only because of the bonfires. La Jolla is such a lovely area that it's almost painful not to visit every day.