I've lived most of my life in New England, so I've been to New York...200 times? Some of it's totally lost its lustre, but I still love Broadway shows, and my sister lives there, and lots of my family's in the area, so I keep going back even though Times Square makes me want to bash myself in the head.
I've been to Toronto at least 11 times, and it's totally lost its lustre, and that's why I like it. It feels like the second home that New York doesn't feel like. I have favorite stores there rather than favorite museums.
Also, I'm going to Montreal in July for the second time this year. I love it there too, but lately the weather's been weird when I go.