Well, the Include contradicts the where. Include says, "Load all tags." The where says, "Load some tags." When there is a contradiction between the query and Include, the query will always win.
To return all tags from any item with at least one tag == text:
var items = from i in db.Items.Include("Tags")
where i.Tags.Any(t => t.Text == text)
orderby i.CreatedDate descending
select i;
(Untested, as I don't have your DB/model)
Here's a really good, free book on LINQ.
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