When you're already dealing with steep menu prices, faltering conversation, and anxiety that your date's hoo-hoo might be too big for your soldier, the last thing you need's the pressure of blindly choosing the wine. Turn that frustrating responsibility to your advantage: Wined Up, opening tomorrow.
An airy loft of a lounge situated above Punch restaurant, WU's goal's to make wine selection approachably fun, and less saturated with panic sweat. Instead of a sneering steward brandishing an indecipherable list, they present you with an awe-inspiring hundred-foot wall stocked with 3000 bottles -- any of which you're free to grab, take back to your table, and guzzle as if you had 2999 more at your disposal. They also provide info packets on vineyards/wines, and a wall-map, so you won't get overwhelmed and meekly order a light beer. The process is so engrossing, by the time you're done you'll have passed a lively, drunken evening without discussing your date's rent, her job, or her unconvincingly positive attitude about staying single in New York City.
WU offers food as well, with meat-heavy small plates running $4-$15; pair that with the modest booze prices (most bottles are $25-$55, by-the-glasses, $6-$15), and you'll be able to afford a second date, or, even more tantalizing, a top-of-the-line mini-trampoline. If you actually know wine, you could hit the mother lode: the owner stashes a few choice bottles from his private cellar in the wall (e.g., an '82 BV Cabernet). Sniff one out and it's yours for ~$50, even if the retail value's ~$200-$250. Prize in hand, the only thing capable of tanking your date would be your petulant refusal to share.
See the menu and the wine list (if you're companionless, check out the "Drinking a lot, alone?" section)