21 dating questions
If you could pick one, would you rather have infinite money or love? If you could undue anything from the past, what is it? If you had unlimited money, what would you do with it? What are the craziest things you’ve ever done with someone else? If someone in your family passed away, which person would surprise you the most? What or things or person has influenced you the most? If you were able to see in the future, what would you tell yourself or want to know?
When was the last time you cried in front of someone else? What’s the right number of people to invite over a Friday night? What’s one thing you’ve learned that most people don’t know how to do? How do you spend your free time, and where do you like to go? What is one habit you’re the most proud of breaking? What is one thing you were afraid to do, but felt amazing after you accomplished it? When you're trying to get to know someone new, you can only text "what's up" so many times. When my husband and I were still dating, I pulled up the list one night and suggested we play the “questions game.” We also mixed it up by seeing if we could guess what the other person would answer.
It was a lot of fun, but also a very profound experience and we ended up learning so much about each other (and about ourselves! To this day we make an effort to spend time asking each other deep, meaningful questions that go beyond ‘how was your day?
Would you rather live in a small house with an amazing view, or a massive mansion in a subdivision? What’s the best piece of advice you’ve ever received from someone?