For years I found myself in the dating game, going on Hinge date after Hinge date, feeling like I was looking for love in all the wrong places. People approach the dating scene from all angles. There’s the casual dater, the semi-casual dater, the one looking for something serious, the other one looking for a rebound, and it goes on and on.
Once I was past the initial post-college glow though, trying to understand what it was that I was really looking for took me a little bit of thinking. Once you get past the small talk and the surface-level stuff, you really want to understand the other person on a much deeper level.
After plenty of time thinking about what actually mattered to me, I came up with a quick little list. Starting airy and playful, I get into some really thought provoking questions that help me genuinely understand the person across from me, their dreams, vulnerabilities, and values.
I realized that I wasn’t looking for love in all the wrong places, I was just asking all the wrong questions.
Here are 19 questions to really get the conversation turned up and find if they’re compatible for you.

- What do you think about when you wake up/go to sleep?
- What makes you the most happy/brings you joy?
- What’s your biggest aspiration?
- What’s your biggest fear?
- What’s your favorite attribute about yourself (physical/non-physical)?
- What’s your biggest insecurity?
- What’s your favorite and least favorite habit you have?
- What do you stand for?
- What do you believe in?
- When are you at your most confident?
- What motivates and drives you?
- How do you view other people of differing backgrounds, socioeconomic classes, races, sexual orientations?
- What are you looking for?
- How do you treat others?
- How do you treat yourself?
- What are the three greatest values you live by?
- What is your definition of love?
- What are you looking for in a partner?
- What do you feel your purpose in life is?