The Wine Source. This place is a) huge b) has knowledgeable staff and c) has a great selection - plus, it's in Hampden, across the street from my very first apartment, which makes it sentimental and awesome.
I bought NINE bottles of wine - all under $12.00 - and all a variety of recommendations from the store employees. They have signs on recommended bottles that read "No Brainer" and have a brain with a slash through it - which makes it really easy to select the featured wines (and it's cute and silly and makes me laugh).
The shopping part was a blast, so I'm betting the drinking part will be even more entertaining - stay tuned!