Squash blossoms are the only flowers I genuinely love cooking, probably because they can take the abuse. Want to stuff them with cheese, batter them, and then deep-fry them until golden? They'll stand up to the challenge.
And, in this particular case, want to cook them down with chiles and tomato, and then fold them into cheese-laden quesadilla? Why yes, that's not a problem at all. Not only will the squash blossoms triumphantly hold up, if you treat them right, you'll end up with a truly memorable dish.
Cut from the ends of squash and zucchini, the flowers have a sweet essence, which recall the vegetable they came from, but without any of the bitterness you might encounter. So while they don't have to be treated like dainty little treats, you also wouldn't want to completely cover up their flavor. I paired them with some equally sweet and acidic cherry tomatoes and a little jalapeño, for a slight kick.
To help balance out those flavors, I cooked the filling in bacon fat, though you could skip it and use a vegetable oil if you'd like. This is right on the edge of too much, but in the end, the squash blossoms are still the most important component.