(for Ages Under 16)
Ask your dates to dress up really nice. However, pick them up dressed in casual clothes. Go to a fast food restaurant, then to a bowling alley for a couple games and maybe some pool (you'll learn whether your date is flexible).
Try playing tennis at night with a fluorescent painted ball and a fluorescent string taped along the top of the net.
Go to the mall. As couples, tie a single hand together. Each couple then creates a portrait of a stranger with crayons on a drawing pad (the subject decides the winner). The first couple to five wins. The losing couple has to pay for the others ice cream.
Go to a thrift store with a camera and have a competion with your date or another couple on who can find the ugliest, craziest, hippest, etc. outfit (and take pictures).
Make homemade ice cream and then have sundaes. If you don't have access to an ice cream making machine, here's a twist. Use ziplock bags. Here's a recipe that works. Take 2 cups heavy whipping cream, 1/2 cup sugar, and 1 teaspoon vanilla extract and put it in a quart-sized ziplock bag. Then seal that bag in another quart-sized ziplock bag. Put that double-sealed bag into a gallon-sized ziplock bag, and add 1 cup of rock salt and fill that bag 2/3 full with ice (crushed, if possible). Wrap that sealed bag in newspaper (several layers) and tape it up. The newspaper protects and insulates your creation. Shake the mixture for 15 minutes (you can carefully toss the bags back and forth to each other), then it is ready to serve.. If you can wait, put the mixture in the freezer for 2 hours to allow the ice cream to become more firm.
Find a hill with enough snow for tubing. Dress warmly, and pack extra dry clothes, just in case. Afterwards, make a fire and serve hot chocolate and chili.
For a double date, each couple gets 10 dollars. Then you go to the dollar store and you have to buy and make something for the other couple. You can make whatever you want. Be creative.
Get together with another couple or two and go on an ecology hike. As resources, get a Boy Scout fieldbook or conservation manual and visit a preserve or wetland or another outdoor setting. The group can participate in damming washes, planting grass or trees, or a clean-up project.
Wear old clothes that can get ruined. Collect spoiled tomatoes or peaches (negotiate at the local fruit stand). Find a vacant field, and have a food fight.
Have a contest with another couple to see who can build the biggest and best snowman. Afterwards, have hot chocolate or spiced cider in front of a warm fireplace.
Go to a formal dance. Afterwards, change into some casual clothes, and go bowling.
Write your own script, using nature as the setting, and film your own movie with a portable camera.
As couples, place 10 items from a store into your shopping cart, then meet at a pre-designed spot. Trade shopping carts, and see who can put back all of the other cart's contents in the right places in the shortest amount of time. For an added twist, write down the product on the same shelf to the immediate right. Losers get to buy ice cream.
Go to a scary movie, and make fondue afterwards.
Buy three blue ribbons and come up with different contests for the evening (i.e. pool, bowling, ping-pong, card games, etc.). The couple that wins two or more competitions receives dinner made by the other couple.
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