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Funny you mention that, I used to think exactly the same way in comparative costs of food. I've actually found since we made our switch, healthy eating costs us less per month. The reason is that we have found that most restaurants have unhealthy food - even when they try to be healthy. So instead of eating out all the time, my wife and I cook at home now. We can easily put together a meal for both of us consisting of whole grain rice, lightly steamed or seared vegetables, and a fish/chicken/pork protein for about $10. That's $5 per person, and there's usually leftovers for lunch the next day. Sure, we splurge from time to time with different vegetables or meats, but for the most part it is very cost effect. I take packed turkey sandwiches for lunch on wheat bread, with carrots as a snack - $3 max for lunch.

I've actually found that after a year of preparing our own food without all the extra grease and sugar that restaurants use to make their food more attractive, eating out is less appealing every day.

Where I find being healthy is expensive is in the cost for a gym or other motivating activity. Exercise by yourself is a difficult routine to stick to. And when you are working long days, it gets even worse. It took my wife forcing me into the first steps to make it happen.

I can also tell you this. Before I changed my diet, I was really tired at work, my sleeping patterns were off, and I always felt tired - too tired to work out for sure. What I didn't realize was the white flour, and added sugars, where sapping my energy in ways I couldn't imagine. Also, the more out of shape I got, the more tired I was.

I find by running a couple of miles in the morning before work, I have energy that lasts all day - even though I'm doing more activity than before. It's a strange thing indeed.

Is it difficult to make healthy choices at the supermarket when there are so many unhealthy options? Definititely.
Is it a challenge to control portions when things are always "super-sized"? Yes.
Is it the supermarket's fault? Absolutely not.
For the majority of people, weight gain and obesity are a direct result of consuming more calories than they are expending. We cannot blame the supermarket for weight gain, most people know what they should be eating and simply choose not to. Blaming others is always easier that accepting personal responsibility for our actions.