HowAboutWe is all about dating how you want to — not how you’re supposed to.

So today we’re kicking off our Break the Dating Rules Contest:

Between now and Monday, January 24th at noon, anyone who proposes a DC date on HowAboutWe that breaks one of the following rules will be automatically entered to win awesome prizes:

Rule #1: Don’t touch your food – it’ll look like you were raised in a pigsty.

BREAK IT: Propose the best eat-with-your-hands date. (Because there’s something down to earth about dining with your digits, after all.)

e.g. How about we…do a progressive food truck dinner: Dinner at a banh mi truck followed by dessert at a mini-cupcake truck.

Rule #2: Don’t worry about money – you don’t want to look cheap.

BREAK IT: Propose the best date that costs $15 or less. (Because bargain hunting can be as much fun as dating…so you might as well combine them.)

e.g. How about we… set up a stand somewhere in the city and give out free advice, and then find the best $2 pizza slice in the neighborhood.

Rule #3: Don’t compete with your date – you’ll seem too aggressive.

BREAK IT: Propose the best date where you go head-to-head. (Because a little healthy competition – whether in skeeball or skiing – creates chemistry.)

e.g. How about we…brown paper bag a bottle of bordeaux and play bocce ball in the park (loser buys dessert).

On Tuesday, January 25th, we’ll post our favorites in each category.

Then the voting begins! If your date idea gets the most votes, you could win:

For the best eat-with-your-hands-date: Churchkey will reward you with a $200 gift certificate.


For the best date under $15: well…a penny saved is a penny earned, right? Just kidding. HowAboutWe will cover the cost of your next three HowAboutWe dates, subject to a $100 cap.


For the best competitive date: H Street Country Club is offering a great date package for you with a special dinner for two at their President’s Table (which includes award-winning margaritas), followed by miniature golf, skee ball or shuffleboard.


Good luck! Now go propose a date.

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