10 Questions to Ask on a First Date
- Hakima Tantrika
- Jul 8, 2021
- 3 min read
These simple questions will allow for a greater connection

Babe, are you ready for exciting dates? The kind full of stimulating and playful conversation? Make it happen for yourself by upgrading the questions you ask. In this article, I’ll share 10 questions with you that will provide for excellent conversation on your next date.
They are engaging, thoughtful, and will help you keep your dates light and enjoyable. Good conversations are not about the quantity of questions, but the quality.
There are few rules to take into consideration beforehand:
Avoid asking only yes or no questions, and always leave room for follow ups. We don’t want our date to feel interrogated, rather that we’re genuinely interested in them. By asking open ended questions, we create space for genuine answers.
Listen attentively, as even an amazing question can’t make up for poor listening skills.
So without further ado, here are 10 questions to ask on a first date.
#1: What is something that you’ve always dreamt of doing?
Asking this will give you insight into the mind of your date. Knowing their dreams, if they have them, will tell you a lot about their values. Being aware of their values will help you decide if you want a second date.
#2: What’s one thing your family doesn’t know about you?
There is always room for secrets, no? And what a better place than a first date to share some vulnerability. This question will have them show you their naughty side. It will also give you a brief glimpse into their relationship with their family.
#3: What is the worst date you’ve ever been on?
We have all been on bad dates. Sharing these experiences can be bonding for you two. Knowing just how bad it’s been can bring some laughter to the date, and laughter is always a good thing. Plus, if you’re nervous about the date, knowing what made the other dates bad can give you a guideline of things to avoid.
#4: If you could solve one problem in this world, what would it be?
Everyone has a heart. By sharing the altruistic parts of ourselves, we share the best parts. Seeing your date's highest hopes paints a picture of what kind of person they aspire to be. Depending on what kind of person that is, you may not want a second date.
#5: What part of your body do you love the most?
In today’s world, criticism and self-judgement are on the rise. Ask anyone what their weaknesses are and they’ll write you a book. That’s why asking your date about what they love is so important. It will shift their mood to be more open and pleasant, as both of you will be receiving that which they love the most about their body. This can be an excellent way to heat up the conversation.
#6:If you wrote an autobiography, what would the title be?
The story of someone’s life can be very revealing, and how they view their own story is even more so. How they answer this will show you how they view their past, and how they hope their future to go.
#7: Where is one place you would recommend I travel to?
Travel helps grow and mature someone. Hearing travel stories will give you a wider perspective on your date. Plus, by the end of it you may have a few new destinations on your list to visit.
#8: What achievement in your life are you most proud of?
Hopefully your date has some achievements they are proud of. How they answer this question will show you both how they’ve lived their life so far, as well as how they value themselves. Knowing your date's history is how you get to know them after all.
#9: If you could have drinks with any person, living or dead, who would it be?
With many icons to choose from, you’re sure to get a great answer. A good follow up question would be “what would you most want to know from that person?”
#10: What’s one secret fantasy you have?
This one is best saved until later in the evening, when things have gone well. It doesn’t necessarily have to be a sexual fantasy, but if they choose to share that with you, then it’s even better. Knowing the things they keep only to themselves will have you knowing your date more intimately in no time.
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Moving beyond simple yes or no questions will be your biggest goal. By giving your date open ended questions that stimulate their mind, you’ll be demonstrating your interest in getting to know them. Remember, always be ready to answer these questions yourself, because your date will want to know about you too.
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