13 Light Questions To Ask On First Dates That Will Lead To Deep Answers

In my experience, first dates are the worst. Especially when you're meeting someone for the first time via that dating app life. There's so much anxiety and expectation that it can even cause dread. By the time you're there sitting in front of each other, you've forgotten about everything you planned on talking about, and the long pauses between exchanges are excruciating. It's hard to have a positive attitude when you're tongue-tied.

Basically, all you want is to get into the deep questions about life and find out what kind of person this is and whether or not you have a future with them. Alas, social construct and manners don't always leave room for the kinds of questions you really want to ask without even more awkwardness. Which is exactly why I've put together a list of questions that seem surface and casual, but actually lead to deeper conversations and character exploration.

These questions are all tried and tested and have all lead me to a clearer idea of the person I'm sitting across from. They're also great questions to ask to fill the quiet spaces that tend to emerge when you're talking to a stranger. So if you're on a date and you're having trouble gauging the person you're with, try some of these questions and see what they're really made of.

How Do You Spend The Holidays?

This question will bring you towards a few answers. You'll find out about their family dynamic, the state of their parent's relationship, their traditions, their religion, their culture, and maybe even their attitude towards their family.

What Did You Study In School?

This gives the person an opportunity to tell you about what their passions and curiosities were and if they're still the same. This also opens up the conversation to talk about college and what that experience was like. Maybe they studied poetry in college and now work in finance. Talking about school will help you get a better idea of their interests and dimensions.

What's The Difference Between Your iTunes Now And When You Were In High School?

Maybe in high school they only listened to emo music and now they listen to folk music. Maybe they grew up listening to country and now love rock. Maybe they've always only every listened to symphonies. You can learn a lot about someone through their musical taste, and even more through the evolution of their taste.

Have You Read Any Good Books Lately?

Some people don't read because they're too busy to or it's not a priority. This can be a deal breaker for some. Instead of being accusatory and asking "Do you read?" try asking "which" good books they've read lately. Give them the benefit of the doubt without and judgment either way.

How Was Work Today?

It's a surface and polite question to ask, but might open up the door for them to talk about their job, their satisfaction with their career and a glimpse into what their every day life is like. When you learn about what motives someone, you learn a lot about their heart.

What Shows Or Movies Are You Watching?

First of all, if you like the same show or movie, you can geek-out together over it and that's a great icebreaker. If you don't watch the same kinds of media, you can ask them about what they like and get a secret glimpse into them when you they don't know you're looking.

What Time Do You Wake Up In The Morning?

Are they a morning person? Do they have a strict routine? Does their life change day-to-day? Do they have sleep issues? Do read or run before work? It's such a simple and natural question to ask, especially when you're out late with someone, and you'll probably get a lot of information out of them with it.

Are You A Good Cook?

This will answer a few questions for you. Do they make their own food? Do they enjoy cooking? Do they take the time to enjoy meals? Are they out every night? Do they order in and eat in front of the TV? You'll learn about their lifestyle and food values right away.

Where Did You Grow Up?

Maybe their family lives across the country and they only see them rarely. Maybe they grew up in the same town and are deeply rooted. Maybe they moved around a lot or between two parent's homes. There are a lot of possible answers that can come of this question and all include more than just a one state answer.

Do You Keep In Touch With Friends From Back Home?

Some people keep in touch with their friends from childhood and are super social. Some people outgrow their old friends or keep smaller social circles. Find out what kind of friend and social being your date is by asking about old friends. It's a lot more polite than "Do you have a lot of friends?"

Have You Been To Any Fun Weddings This Year?

Get a sense their feelings towards marriage by asking this question. Do they excitedly tell you about a great wedding? Do they roll their eyes and say they wish their friends would all slow down? Do they say they don't believe in marriage and say no? Do they tell you that they don't go to weddings because they hate them? There are so many ways your date can answer this question and chances are, it will be telling.

What's Your Sign?

This opens up big spirituality questions. Do they know their sign and know all about it? Do they not believe in astrology? This gives them an opportunity to explain their personality to you and their greater beliefs in the universe, or lack thereof.

Where Do You Want To Go On Your Next Vacation?

Find out if this person likes to travel. How curious they are in the world. How they like to spend their time off and what places are alluring to them. Maybe they don't like to go far from home, maybe they've seen the whole world — either way, it will give you some insight into their life before you and give you something to talk about.

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