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10 Unique Yet Shockingly Telling First Date Questions

Ava Ferriero Student Contributor, Boston University
This article is written by a student writer from the Her Campus at BU chapter and does not reflect the views of Her Campus.

The idea of a first date is intimidating. But why?

You have yet to establish shared experiences, and you’re unsure whether you have any common interests. It can be scary and awkward to go out with someone solely on finding each other attractive.

That being said, it is helpful to memorize a few questions that could be useful during these daunting dates. Do not fear…that is what I am here for! Here is a list of engaging, fun questions that reveal critical information about the person you’re seeing.

WHAT WOULD THE TITLE OF YOUR BOOK BE?

A book title sums up the main idea and overall theme of a story. Everyone has their own unique narrative. However, it differs based on the person you are and the life you hope to have. 

There are a lot of ways to go about this question. Your date can be silly, and give a joking title. They may be serious and give a straightforward title. They can even be poetic and propose a title that is personally metaphoric.

No matter their response, this question grants you the chance to grasp how your date views life. It tells you who your date is as a person, but also how they want their story to go. 

WHEN DO YOU FEEL THE MOST YOU?

As you’re getting to know someone, it is helpful to understand their interests. This question presents when your date is most vulnerable. Knowing this in the future can help you understand who your partner is when they’re in their element. 

This question shows your date’s soft spot. They could say it is when playing their favorite sport, when at a specific place, writing a Her Campus article, or simply drinking an iced coffee from Starbucks. The best thing about this answer is that it differs for everyone. Yet, it presents their values and what kind of experience brings out the best in them. 

WHO IS YOUR IDOL?

We all have people we look up to and aspire to be like. Even if they give an unserious response, it still broadens your sense of the person they want to be. These role models reveal a lot about the traits we hope to embody.

When we look up to someone, we attempt to mirror their characteristics. Knowing who your partner aspires to be explains some of their actions.

What was your childhood like in one word?

Whether it was good or bad, our childhood shapes us. To understand someone’s beginning is to deeply understand who they are now. However, that is a little too deep to dive into on a first date. Rather than asking them about the nitty-gritty of their childhood, ask your date to sum their childhood up in one word.

This way, you get a sense of how their life began without overstepping. And, if your date seems comfortable with the question, you could even ask a follow-up.

WHAT IS A HILL YOU WOULD DIE ON?

This is an important question to ask before pursuing someone. It reveals what their strongest belief is, and how truly picky or stubborn they are.

It can also tell you if you are compatible, depending on whether you agree or disagree on their strongest viewpoints. If you disagree on a moral that grounds them, they might not be the one for you. 

What compliment do you receive most?

This is my favorite question!

Not only is it a confidence booster to talk about good qualities one has, but it also presents the most noticeable quality of your date. It tells you the good attributes other people see in them.

It can also be flirtatious, which spices up your date. You can tell them you agree with the compliment, or give them a new one they’ve never heard before. It is a great segue into being romantic and cute.

WHAT DO ALL OF YOUR LOVED ONES HAVE IN COMMON?

This wholesome inquiry makes your date think about all the people they love, while also allowing them to consider the characteristics they are attracted to in others. And, it is a good question to provoke self-reflection.

At the same time, it allows you to see if you’re a good fit for your date. If they say most of their loved ones are creative, and you are also creative, you may be their type!

Who do you think you were in a past life?

Do they think they were a past president? Do they think they were Einstein? What about English Royalty or an artist in the Renaissance? Either one reveals the type of person your date is at their core. It portrays how free their spirit is. And their answer represents their strongest feature and how old their soul may be. 

Disregarding money, what would your dream day look like? 

This is such a fun idea to consider and discuss! It gives you a glimpse of your date’s routine and favorite things to do. It shows the things that are most valuable to them based on what they include in their “dream day.”

And even better, their response can also give you future date ideas, ones that you can remember and then surprise them with later.

What do people misunderstand about you the most?

How one is perceived versus who one really is can completely differ. It is easy to be blinded by public opinion. This question allows clarification on things that people do not understand about your date.

It will open up the opportunity to be vulnerable. Hopefully, it can prevent future misunderstandings between you and them! 

First dates can be nerve-inducing, but they can also be exciting, fun, and full of new possibilities! If you keep these questions in the back of your mind, you will have your date talking all night.

And hey, if they work, remember to send me the wedding invite!

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Hi! I am Ava and I love to write about everything and anything. My major is journalism (shocker). I also like cats, coffee, walks, music, Boston, and social media!! I hope you enjoy my writing <3