There are no dumb questions. I think you're asking about map projections. The only way to really see the true, relative sizes of the states is with a globe (this can be a digital globe, like Google Earth, or an actual physical globe). To make the round Earth flat, you have to apply a map projection.

There are many projections, each suited to a different need. You're probably with the Mercator projection, which is great for navigation purposes, but greatly distorts regions closer to the poles, making, for example, Greenland appear to be as large as Africa, when in reality, Africa is 14x larger.

What you're looking for is something more like an "equal area" projection, which puts a priority on maintaining the relative sizes regions. Here is the North America Albers Equal Area Conic projection.