This is one of my favorite date experiences to try but can go a bit sideways if not done wisely. On an ordinary and unexpected evening, wake your loved one in the middle of night and tell them you have something you want to show them. If they are not the type of person who sleeps 20,000 leagues under the sea or is incredibly irritable being woken, take this willing person on an adventurous late-night date surprise. Arrange a romantic rooftop date for your loved one with the help of a friend or family member, go for a late-night joyride, or an all-night diner. Spend the next couple hours in a quiet city driving the streets or highways in darkness. Play some romantic radio greatness, wax poetically, and appreciate the experience of being two rare people up and exploring the world around them. Time your drive in such a way to take in the sunrise from a scenic vantage point in the city. For a change of pace or a person who loves surprises, you can’t go wrong.