You've done the same old dinner-and-a-movie so many times it should be dragged out to the curb and put out of its misery. There's no way you're going to impress that stranger you met on CraigsList with that old routine.
Our #1 tip for planning a date? Actually, you know, PLAN one. That means thinking about it ahead of time rather than while you're waiting for your date outside the Metro with sweaty hands, and then steering for the first Thai restaurant you see. So check out the first in a series of neighborhood-focused date suggestions, and never humiliate yourself in front of a random Internet stranger ever again.
Want to show off your playful side? Bedrock Billiards (1841 Columbia Road NW) is a great place to start a date. The retro spot only has seven pool tables, which means it just might push you two closer together. Loosen up with a Stella or a Guinness on draft, and grab a pool cue or sink into a comfy sofa. Pool tables are $10 per hour for two people during peak hours, but females play free on Wednesday. Guys, if your pockets have more lint than cash, this is where and when you take the girl out.
While the night is young, head to the District of Columbia Arts Center (2438 18th St. NW) to see the work of local emerging artists. Admission to gallery exhibits is free; plays fall in the $5-$20 range -- still manageable, even with a ridiculously priced fro-yo afterward. A current exhibit, "The Twelfth Man," features a series of color photographs of grown men having zany fun with trampolines, pogo sticks and other things that really never stopped being fun even though you grew up.
As the night comes to an end, pick up a hefty slice of pizza at one of party-tastic pizza spots on the 18th Street strip. Yes, we're actually suggesting Jumbo Slice as the way to end a date, but seriously? Nothing will cut the pretension faster than dodging dripping grease and making fun of drunk people with your date. Provided your date is not, in fact, one of those drunk people.
All jokes aside, if you're not feeling the pizza grease (seriously? you're NOT?), then Duplex Diner (2004 18th St. NW) is the spot. This diner -- with a full-service bar -- has an atmosphere caters more to late-night partiers, but old-school goodies like meatloaf, grilled cheese, onion rings and tater tots aren't typical date fare. Which makes it way more fun.
What you do after that is your own business. We don't want to know. Really.