Don’t you just love when the honeymoon phase is at its peak: The chemistry is electrifying, all your spare time goes into happily talking to them, and you’re asking whimsy questions like “what’s the color of your eyes when the day breaks?”. But then, a month or two in, the dust settles. You realize that while his eyes are brown at all times and you both love a g and t, you have no idea how they handle conflict, what they think about feminism, or if their version of commitment matches yours.
In modern dating, we often mistake chemistry for compatibility. While chemistry ignites the passion between you two, compatibility keeps the flames burning. To find out if you’re actually aligned and not just infatuated, you have to move past the “What’s your favorite color?” phase and dive into the deep end. Here are over 21 conversation starters designed to peel back the layers and see if your lives are headed in a complimentary and sustainable direction.
The Foundations: Values & Worldview
These questions get to the core of who a person is and what they stand for.
- What are your three biggest non-negotiables in a partner?
- How do you define “success” for yourself? Is it status, peace, or something else?
- What is a belief you held five years ago that you’ve since changed your mind about?
- How much of an influence does your family’s opinion have on your personal choices?
- What is the one thing you want to be remembered for?
- Do you believe in “soulmates,” or do you believe relationships are built through work
- What do you consider your best quality?
- What social or political issues are you most passionate about?
- How do you prioritize your spending? Are you a “save for a rainy day” or a “life is short” person?
The Dynamics: Relationship Styles & Conflict
These questions get to the way love, anger and everything in between will potentially be expressed by this person
- What is your love language, and how do you like to receive affection?
- How do you typically react when you’re feeling overwhelmed or stressed? Do you pull away or lean in?
- What did your parents’ relationship teach you about what to do (or what not to do)?
- How do you handle a disagreement? Are you a “talk it out immediately” or a “sleep on it” person?
- What does personal space look like for you in a relationship?
- How do you define cheating or a breach of trust?
- Do you have any couple you stan? Who and why do you admire their relationship?
- What is your biggest green flag in a partner?
- How do you feel about maintaining close friendships with exes?
- When you’re upset with me, how would you prefer to bring it up?
The Future: Ambition & Lifestyle
These questions tells you if you are wasting your time or not.
- What is your dream lifestyle?
- How do you feel about marriage as an institution?
- Do you see children in your future?
- How much of your identity is tied to your career?
- What is your ultimate travel bucket list destination?
- How do you feel about relocating for a partner’s job or vice versa?
- Where do you see yourself living in ten years?
- What legacy or impact would you like to leave behind in the world? How would you like to be remembered by others?
The Internal: Emotional Intelligence & Past
These questions get to who they are within, who they are when they aren’t performing perfection.
- What is the hardest thing you’ve ever had to overcome?
- What is your biggest regret, and what did it teach you?
- Are you a person who lives in the past, the present, or the future?
- What is one thing you’re currently working on within yourself?
- How do you handle failure?
- What is the most common misconception people have about you?
- What makes you feel the most vulnerable?
- Do you believe in second chances?
- What is something you’ve never told anyone because you were afraid of being judged?
- How do you want to be comforted when you’re crying?
The “Vibe Check”: Fun But Telling
These questions may be lighthearted, but many times they reveal the deepest truths.
- If you could have a do-over on any year of your life, which would it be?
- What is the best piece of advice you’ve ever received?
- If we had a completely free Saturday with no chores and no budget, what would we do?
- What will you describe as ‘see finish’?
- What is your guilty pleasure that you’re secretly proud of?
- How much alone time do you need to feel like yourself?
- Dinner with Jay-Z—or whoever their role model is—or 1 million dollars?
- If you could dinner with any three people, dead or alive, who would they be?
- What are you most curious about right now?
- What is one question you’ve been dying to ask me but haven’t yet?
How to Use These Questions
The goal isn’t to run through this list like a job interview at a boardroom table. Use them as “seed” questions. Pick two or three over any date or hangout. Take his answers as they are instead of deluding yourself so it fits the idyllic picture of how you imagine him in your head—rookie mistake. If you ask a question, be prepared to answer it yourself with 100% honesty. Alignment isn’t about finding someone who gives the “correct” answers, it’s about finding someone whose truths don’t clash with yours.
