I just completed a new feature that I know will help initiate more ladder matches. It is called "Looking to Play".
You will now see a new "Looking to Play" tab on the ladders. On this page, players can view and post listing of specific times they would like to play a match. For example, you could post a listing that you are looking to play a 4.0 player next Saturday morning at your local park.
The idea is, other players will see these listing, and initiate a match.
Send me your comments and suggestions. I would love to know what you think.