You're right in saying that it is more complicated with a web app. In a windows app, whenever you run the C# code, whatever happens, happens at that moment. It's pretty straightforward. However, in a web app, all of the C# runs before the page is even rendered in the browser. Therefore, C# in web forms can't really pop up a window.
In order to get a popup, you'll need to do that with JavaScript. The textbox inside the popup should be an
<asp:textbox>
control. You can use the
Ajax Control Toolkit[
^] if youre most comfortable with .NET controls. If youre comforatble with jQuery, you should check out
jQuery UI[
^].
--Amit