Sorting Posts By Date problem

Hi all,

Terrible title, I know. Wasn’t sure how to explain this one quickly. Here is my site: majesticdetroit.com

I am using this code to sort my events in my sidebar by a custom date field:

<?php $recent = new WP_Query('cat=45&showposts=15&orderby=meta_value&meta_key=Date&order=ASC'); while($recent->have_posts()) : $recent->the_post();?>

Basically, what is happening is that events with a date of 03/10/11, or anything in 2011 are being sorted and showing at the top of my events list. I need to know how to get around this. Is this a WordPress issue? Or is it my code?

Any help would be great!