Thrift Store Style Challenge
Set a $20 budget per person and head to the wildest thrift store you can find. Challenge each other to find the most outrageous complete outfit for the other person to wear for the rest of the date.
Try on your selected outfits in the dressing room and don't hold back the laughter. Purchase your favorites and actually wear them out to a casual restaurant or coffee shop, fully committing to the look.
Take ridiculous photos throughout the evening and create stories about your new personas. Keep one item from your outfit as a souvenir and promise to wear it on your next anniversary.