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5 Deep Questions to Ask Your Date

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After establishing general compatibility with someone, here’s five questions to get to know your date on a deeper level. 

1.What makes someone trustworthy? After your date shares an organic story or insight about a bad relationship from their past, this is a great question to follow up with. Trust is an essential part of healthy relationships so it’s helpful to understand your date’s experience with and understanding of trustworthiness. Plus, if they have inner awareness and cherish their integrity, they might even tell you why they consider themselves trustworthy. 

Keep in Mind: A date who’s unable to tell you what makes a person trustworthy might not have strong emotional awareness (they don’t understand their feelings), or, in the worst case scenario, they might not understand empathy and may lack the ability to put themselves in others’ shoes (they could belong to the dark triad: sociopaths, psychopaths, narcissists).  

2.What’s your favorite thing about life? While most of us could easily think of what we dislike about life, our favorite thing about life could be more telling. Your date’s response would give insight towards which aspects of life are meaningful to them, what they’re more inclined to notice, and, depending on their answer, could even be a treasure box from which you draw endless future gift ideas (birthday, holiday, anniversary, etc.). 

Keep in Mind: If your date can’t come up with an answer (I once knew a man who legitimately couldn’t), it could mean a number of things: maybe they live on autopilot and don’t reflect on their life experience often, perhaps they have a more melancholy outlook toward life, or might even be depressed. Ultimately, knowing their favorite aspect of life (or lack thereof) will allow you to better understand how your date experiences the world.   

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3.What’s a regret you don’t want to have at the end of your life? Your date’s answer could reveal how much awareness and foresight they look forward with. Do they have hidden motivations behind their lifestyle? Their answers might even help you predict what they might want within the relationship (more regular travel, socializing more in meetups, etc.). 

Keep in Mind: If your date has no answer or says they haven’t thought of it before, this means they might live their life more in the moment rather than in Big Picture view. While living life in the present can have numerous benefits, it’s good to know that they’re less likely to think ahead on big things. 

4.What’s the most painful thing you’ve ever experienced? If they ask, ‘physical or emotional,’ it could be fun to leave the question open with ‘both.’ After hearing their answer, a good follow up question is, “Which is worse, physical or emotional pain?” I find that those who’ve experienced severe emotional distress will say emotional, while those who haven’t are more likely to say ‘physical.’ 

I theorize this is because catastrophic physical injuries are easier to comprehend than catastrophic emotional ones. Despite most people knowing what heartbreak, grief, etc. are, they can’t truly discern the misery of these events until it happens to them. 

Keep in Mind: If they explain an emotional distress, ask more questions to understand how they coped and recovered from the pain. Did they start therapy, pick up a healthy hobby, turn to alcohol or drugs, being self-harming, etc.? Their reply can provide insight into how you might be able to best support them should a severe emotional distress occur during your relationship with them. 

5. If you could cure or solve one world problem, what would it be and why? This question is a good way to understand what topic or problem has most strongly affected them or what they care about most. If someone gives a surprisingly deep reply, it can also reveal they’re not afraid of understanding the sadder problems in the world (rather than avoiding them). 


Keep in Mind: Some people intentionally avoid painful or sad topics. If your date doesn’t want to deeply discuss their response, it could mean they’re more interested in Living & Enjoying Life rather than Solving. While there’s no right or wrong way to live, understanding where someone lies on this spectrum will help you understand how they might approach future conversations. Do they enjoy conversations about heavy topics, or do they prefer lighter topics?

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