First dates could be daunting (especially if you’re online dating) because you know very little about the other person’s character, beliefs and values.
Straightforward, generic questions might not get you the genuine answers you want. Besides, questions that are too direct such as “What is your political view?” can make the conversation feel too serious. The last thing you want is to turn the date into a job interview.
So how do you get to know your date more without asking questions that are too personal, too intrusive or too awkward?
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Here are 5 questions that could tell you a lot about their character:
1. What are your best friends like? Why are they your best friends?
Ask them who their best friends are and how they have become close. Usually, people pick friends who share similar values as themselves. Knowing what qualities their friends possess also shows what they highly value in a person.
For instance, my best friend and I became close because we both enjoy in-depth discussions on philosophical topics. Whenever I learn some interesting facts and want to share, he’s always down to listen. This shows that I value qualities such as intellectual curiosity and open-mindedness.
If they’re friends with someone because both of them like gossiping behind people’s backs, perhaps they’re not that nice of a person to date.
2. What’s the favorite compliment you have ever received?
Asking this question can often lead to happy stories. Your date might recall a moment they are especially proud of. The truth is, people’s favorite compliments are often related to what they value the most in themselves.
For example, if someone tells you their favorite compliment is from his boss at the workplace, perhaps they are someone who highly values their job and professionalism. If you absolutely hate workaholics, you might want to think twice about dating them.
Occasionally, this question also opens up a discussion about people’s core insecurities. I once had a date who told me that his favorite compliment was “Your style is always impeccable.” He explained that he often feels insecure about how he looks, so he pays extra attention to dressing up nicely. Not only did I find out that he is really into fashion, but we had a chance to dive deep into a meaningful conversation about our own insecurities.
3. What’s a viewpoint you strongly believe in and what’s a really good counter-argument you’ve heard from the opposing side?
Ask a Christian’s opinion on atheists and someone who supports gun control if they understand why some are in favor of gun ownership. You will be surprised by the amount of people who refuse to understand different views from their own.
No matter how invalid you think the opposing side is, it’s always better to know why the other side holds differing viewpoints. It gives you a nuanced view of the issues you care about and helps you strengthen your own stance. We’re not talking about human rights or climate change, but most controversial and ambiguous topics involve complicated arguments on both sides that are not a hundred percent black or white.
If someone totally ignores the need to understand opposing viewpoints, there’s a good chance they aren’t very open-minded and lack critical thinking skills. It might even tell you a bit about their empathy level.
4. What would you do if you won a trillion dollars from the lottery?
Most people can’t fathom how much money is a trillion dollars. Don’t stop asking after they gave you generic answers like “pay off my student debts” or “buy my parents a house”. Keep on asking what more they would want after they’ve checked off every single wish on their list. Eventually, it will get to a point where they reveal what they truly want if they can live with total financial freedom and zero obligations. This tells a lot about their passion and desires.
On our first date, my current partner told me that he would invest in technologies that help paralyzed people walk on their own again. He said he couldn’t imagine being confined to a bed and that was the worst nightmare someone could go through. He was so eager to take that suffering away that I immediately liked him because of his empathetic nature.
5. Who’s a celebrity or public figure you cannot stand?
Gossiping about famous people is a fun topic for most. This gives people an opportunity to talk about personality traits, behavior or political views they abhor.
They might tell you how they hate Andrew Tate for his misogynistic remarks. Then you’ll know they are someone who cares about feminism. Or they might go on about their hate for the Kardashians. That’s a way to find out they dislike people who are vain or materialistic.
If they despise a mainstream celebrity for random and invalid reasons, you might want to consider the reasoning behind it. Are they a hater? Or perhaps someone who is easily jealous of other people’s success?
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Most people aren’t ready to let their true self shine on a first date.
Sometimes, asking unexpected questions gets the most genuine response out of people and reveals hidden facts about them.
Remember that these questions only offer an opportunity for you to know someone better. There’s a limit to what you can learn about a person on a first date. So unless they said something that was a real deal-breaker, don’t judge too fast and go on a second date!
Thank you for reading my article.
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This post was previously published on medium.com.
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