Welcome to Android Central! On most phones, the Phone app's Favorite/Frequent contacts tab should show your most frequent contact at the top -- but it would still be below any starred contacts (i.e., the favorites you selected in your Google Contacts). If you want the most frequent contact to be at the very top, you'd probably have to un-star all of your starred contacts, so that they don't show up in that tab.
How are you trying to add the Direct Dial or Direct Message widget? In general, long-press an empty part of the homescreen, tap Add Widget, and drag and drop the Direct Dial or Direct Message widget to the homescreen. It should then open your Contacts and ask you to select the contact and the specific number to associate with the widget. I'm not sure what you're referring to when you mention approaching the widget.