As per Jillian D's request, here are details on the dress I wore in the evening of the soccer group date:
Dress: Topshop Cream Lace Mini Dress ($60), purchased in Autumn 2009. It originally had a low-ish back, to just beneath the shoulder blades, but I had my tailor scoop it out way lower. This exact dress is unfortunately impossible to find since it's quite old, but the style is SUPER easy to replicate. Just make sure you don't scoop out so low that when you (inevitably) tug down the dress while walking, you don't end up showing any coin slot action. :)
Dress: This color block cutout dress is an Hervé Leger (possibly a knockoff, but if so it's VERY good) that I purchased from a cut label boutique in Hong Kong in 2011. (For about $200, versus $1200+)
Fun fact #1: If you're ever in Asia, particularly Singapore or Hong Kong, the cut label stores are to die for. A great guide to what "cut label" means as well as how to shop for them is here.
Fun fact #2: This dress has considerable under-cleavage that was blurred out by the editors. I suppose upper-cleavage is television-friendly but not under. :)