You are finding the design process difficult because you are trying to design your site based around an URL space when you should be designing your content documents instead.
Here are skeleton set of media types that would address your requirements.
Media Type: application/vnd.yourcompany.collections+xml
<Collections>
<Widgets href="http://yoursite.com/{9BCCD309-644C-4fb8-A35E-A8B5E6AC4AE8}"/>
<Users href="http://yoursite.com/{BE57DC2D-8FE7-45e3-9362-AF5F607D62B6}"/>
</Collections>
Media Type: application/vnd.yourcompany.Widgets+xml
<Widgets>
<Widget href="http://yoursite.com/{4A7B5583-5D09-4cf3-9781-1084977769C0}"/>
<Widget href="http://yoursite.com/{0D6A72E8-6088-462c-A97A-70BC43E25475}"/>
</Widgets>
Media Type: application/vnd.yourcompany.Users+xml
<Users>
<User href="http://yoursite.com/{6321D95E-7EDB-46b8-9430-AB57EA067B06}"/>
<User href="http://yoursite.com/{0D6A72E8-6088-462c-A97A-70BC43E25475}"/>
</Users>
Media Type: application/vnd.yourcompany.Widget+xml
<Widget>
<Property1>99</Property1>
<Property2>A Description</Property2>
<UsersOfWidget href="http://yoursite.com/{26995C10-CA1D-4f1f-9065-2246A8426DA7}"/>
</Widget>
Media Type: application/vnd.yourcompany.User+xml
<User>
<Name>Joe Smith</User>
<WidgetsOwnedByUser href="http://yoursite.com/{D718A2E6-6ADD-4d6e-A1E7-6DA68EDE0BD3}"/>
</User>
Obviously this set of media types is only one of many potential solutions to your problem. The issue I want to draw your attention to is that that the URL is largely irrelevant. How the documents inter-relate is important. When you look at it this way, it is not difficult to distinguish between the Widgets used by a User and the Users who use a Widget.
Now, how you map this to a set of Rails controllers is a whole other matter. The problem is not that it is difficult to design a RESTful solution, it is just Rails doesn't seem to map very naturally. Not that I have much experience with Rails, so take that for what it is worth. I believe that you should have one controller per resource and the fact that Rails tries to squeeze the list of a resource and the resource itself into a single controller is a mistake. Customers and Customer are two different resources in my opinion.
Edit: Possible set of Urls that might link these resources.
/Widgets
/Users
/Widget/1
/User/99
/Widget/1/UsersOfWidget
/User/99/WidgetsOwned
I would create a controller for each of these endpoints.