2D Drawing Tools Not Working On PC

I am newly using my PC app instead of the ipad for modeling and it seems that my 2D drawing tools do not work on my PC app. Example:

Ive modeled a simple circle with two hole pattern for a plate. When selecting the point to point dimension tool, nothing happens when both points are selected. in this case the midpoint of the circle to the midpoint of the hole.

Anyone have this issue? Maybe a fix?

Are you holding down the Shift button when selecting the second one?

No, but I am now. Thanks!

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