I fly often. Honestly, the flying is the easy part. It's the airports/passengers that are the hard part. That probably doesn't help you with your concerns though.
I'd offer this:
I had a friend who once told me that he thinks of flying like being on a boat. The air is like the ocean. There will be some bumps and dips but that doesn't mean the boat is going to sink. It is normal. He says he actually can enjoy the movement of the plane now where as he used to dread it.
Lastly, flying from Red Deer to Medicine Hat, you will almost certainly be on a turboprop type plane. Don't sweat these smaller planes. They are actually quite a smooth ride. Also, no middle seats!
Think of it as a fun adventure and you'll be fine. People do this everyday.
Enjoy it.
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