I have a circle where I want to add a dimension from its center to the edge of the rectangle it is in. The dimensioning tool won’t pick up the edge of the rectangle. If I start from the edge, it won’t pick up the circle. It’s as if they are in separate planes. I see this behavior both in SketchUp for the Web and SketchUp for iPad. It seems the problem is with me, but I can reproduce this same issue in a new drawing with just a rectangle with a circular hole in it.
Without anything else to go on I’m going to guess that you are trying to dimension to an edge, mostly you need to choose an endpoint, midpoint etc and slide to the place you want.
You can see here if I click the edge it won’t stick, but if I click the corner I can then move it to the correct position and the dimension will adjust.

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