Thanks so much for your response!
I've done some fiddling with it, and it appears to be something with the Max Magazine theme itself. I've mixed and matched various different widgets and it happens the same no matter what widget I use. I've also tested out the exact same widgets on different themes, and there are no overlapping issues.
I have limited experience with CSS, and after looking into it, I've been trying to edit the #sidebar .widget section, since it seems to be universal to all widgets (as opposed to individual widgets). These are the default rules:
There doesn't seem to be any rule telling it to be an absolute positioning. Even after adding "position: relative;" as a rule, it does nothing to change it. So, I'm assuming, there is something else I'm missing.
It's odd that after you resize the window to make it smaller, and then resize it back to full screen, everything snaps in place just fine. I'd like it to just do that upon initial loading.
EDIT: And of course after I said that, I thought to look at what the code looks like in Firebug once I've resized the window, but the only difference is that the "top" value for the absolute positioning changes to fit perfectly, instead of on top of each other.
So basically, something other than the stylesheet is telling the widgets to do absolute positioning and assigning them a "top" value that I'm not quite sure how to manipulate.