What it communicates: I'm on the fence about you.
If you're looking to be as indirect as possible, this is what you bring her. What does a bottle of $50 Bourdeaux really tell her? That you know how to navigate a wine shop? That you want to sleep with her, and decided that getting her drunk on red wine would be the easiest route? Maybe it just means you really like red wine.
A sommelier might be able to decipher what your choice of drink says about you right down to the brand and color of your briefs (Calvin Klein, black). But to the untrained eye, this gift actually says very little. So, if you've only been out once or twice, and think her eyes are pretty, but don't know the name of her cat, go with the Bordeaux. Or Malbec. Or Pinot Noir. Chances are, you don't know the difference anyway.