The key to having a successful date is relaxed conversation and a few laughs while gaining some insightful information about the other person (that is – if you’re looking for something more than a fling). To achieve this sweet spot, you need to be able to ask meaningful questions without sounding like you are interrogating them or interviewing them for the role of Mr or Mrs… because that is just so awkward and intense.

Because I have been on both ends of this uh… situation, and being someone who doesn’t like to waste my time with people who aren’t on the same page as me (when it comes to dating), I came up with these 5 insightful questions which are disguised as fun, playful questions. With them I was able to figure out everything I needed to know about the person I was on a date with. Plus, these questions are fun, will get you and your date laughing and the sparks flying. In short, it won’t feel like an interrogation room.


1. If you were offered your dream job in the location of your choice, what would it be (the dream job) and where would you go?

This question gives you insight into what they love to do, and where they would ideally see themselves in a few years. Their answers can reveal to you how adventurous they are, and how similar your dream goals potentially are.

For example (my answer):

I would be a full-time song writer for a big record company, and I’d like to be able to travel while I work (work from anywhere). But if I had to choose one location to be based in, it would be Brazil. 

What can you tell from my answer?

  1. That I love to write songs.
  2. I don’t want to be famous, I would just like my songs to be heard.
  3. That I love to travel (adventurous)
  4. My favorite place is Brazil.


2. What do you rate this place on a scale of 1 – 10?

This question is an interesting one. It seems to innocent, but you can tell a lot by their answer. Let’s say, for example, you took your date to your favorite restaurant for the date. You took them there because they serve your favorite food, you love the vibe and the meals are cooked to perfection (in your opinion). If their answer is; “Meh, it’s okay. I’d give it maybe a 5/10.” then this could indicate that you have very different preferences and expectations when it comes to food and the types of places you like to go.

I asked my (now boyfriend) this question on our first date. We had both just moved to Hong Kong, and I wanted to find out what he thought of it so far.

His answer:

“Oh, I love it here. I can see myself potentially staying here for a long time. I guess I’d rate it 9/10… but only because I haven’t seen some of the really beautiful places yet. 

What can you tell from this answer?

  1. He likes Hong Kong
  2. He’s a positive and enthusiastic person
  3. He wants to keep exploring the place
  4. He’s thinking about the future

This answer resonated well with me because I loved Hong Kong too and at that point I was wanting to stay there long-term. If I had hated the place, however, I may have looked for someone who felt the same way and wanted to find another place to go with me.


3. If your family were characters of TV shows, books or movies, who would they be? And who would you be?

This is such a fun question but it will reveal SO MUCH about the other person, their relationships with their family,  and their family dynamics. 

For example (my answer):

Well, my dad would totally be the dad from My Big Fat Greek Wedding. He can be really stubborn sometimes, and he’s very loud and passionate, but he’s also a really great dad, and an extremely generous person. He would also be William Wallace because he’s adventurous, fearless and extremely protective over the people he loves.
My mom would be a combination of Miss Fisher in Miss Fisher’s Murder Mysteries (because she’s elegant, a real go-getter, men respect her as a business woman, and she’s quite quirky and fun) and Lilly from How I Met Your Mother (because she’s really kind, caring, has strong morals and is artistic).
My youngest sister would be a combination of Mary from Downton Abby (she’s determined, logical and unstoppable), Jessica Alba in Honey (she’s sweet and talented) , and Timon from The Lion King (because deep down she’s just a big cheese ball!).
My other sister would be a combo of Snow white because she’s extremely kind and caring to all creatures, and Hermione granger because she is beautiful, witty, wise and fearless.
And I would probably be a combination of Sybil from Downton Abby, Beauty from Beauty and the Beast and Ariel from the Little Mermaid. 

You can tell from my answer that I have really good relationships with everyone in my family, and how I perceive each member of my family. You can also tell a lot about who I am and how I perceive myself.

You’re basically asking a very serious and insightful question, but in a very playful and entertaining way.


4. Would you rather be the captain of a pirate ship, or captain of a warship?

Translated, this question would be: Are you care-free, adventurous, out-of the box and a perhaps a little crazy, or are you serious, logical, law-abiding and by-the-book?

Remember to always ask WHY they choose what they choose – because the reasoning may be different to what you expect.


5. What do you want to be remembered for when you’re gone?

Well, we had to have at least one deep question in here!

Their answer will give you insights about what is most important to them.

A friend of mine once told me that if she had to be remembered for one thing, it would be that she loved people well. She was one of the first people I met when I moved to California when I was 18. She was older than me, and went out of her way to make sure that my friends and I (all college students) were well taken care of. When my family visited, she hosted them, made us meals and showed them around town.
She was one of the kindest, most generous and most loving of souls.

That was her greatest value: love.
And because it was her value, she lived it.

She recently passed away. But do you know what people have since said about her? She was so full of love. She really knew how to love people!

My friend, Judy Venn, lived her life incredibly well, and she is indeed remembered for how she showed love to the world.

How someone answers this question will tell you what they value and how they want to live their lives.

Some people might answer “I want to be a famous actress,” while others may say something like “I want to be remembered for being a great husband and dad”.

Whatever their answer, you will be able to tell if their values align with yours.




WHY: With all of these questions (and any other questions you ask), the most IMPORTANT follow up question is WHY.

WHY do they want to live in Brazil?
WHY do they love the restaurant you chose?
WHY do they think they are most like Red Power Ranger?
WHY do they choose pirate ship over war ship?
WHY do they value what they value so much?

Whatever their answers, your response should always be WHY. Because THAT will give you the most insight into who the other person is!


RELATED: 12 First Date Red Flags




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