I've spent the last year trying really hard to up my tolerance for heat in food. Coming from Iowa, and raised in a Norwegian family, the only 'spices' we used growing up were sugar, maybe salt, and maybe a little pepper. But rarely pepper.
I've always been a mild food eater, afraid to try anything that might have even the smallest amount of heat.
Then I realized that I was missing out on some incredible food all because of my wuss of a palate. So about a year ago I started add a bit more heat to my food. It started with my chili, which I spiced with some chili powder, red pepper flakes, and cayenne pepper. I tend to eat my chili with cheese and sour cream, which helped cool my mouth between bites. After a few months, I was able to tolerate a decent amount of heat and was ready to graduate into something heartier.
I took a cooking class at Flavour cooking school in Forest Park where we cooked with pablano peppers. We grilled them and blended them with other ingredients to make a green salsa. It was hot. But I could handle it.
Friday night I cooked up some homemade creamed corn, which called for chipotle peppers in an adobo sauce. They were nice and hot and smokey and they made the dish sing with flavor. And I had a second helping!
So I'm not quite to the point where I'm chomping on jalapenos (jala-painfuls, as someone I once knew used to call them), but at least I'm working my way there!

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