Don’t you just hate the awkward silence on a date when the conversation stalls? You know, those times when you’re smiling at each other across the dinner table feeling uncomfortable? It can really leave you scratching your head wondering what you can say to fill the void. It really makes you wish you had a mental list of good questions to ask to get to know someone.
Unfortunately, those awkward silences can lead to you blurting out a question that makes your date uncomfortable, like: “How did your last relationship end?” or “Have you ever been cheated on?” Yikes, not a great idea.
The rule of thumb for a question is this: avoid asking anything you yourself wouldn’t want to answer on a first date. If you’re worried about coming up with just the right questions to break the ice, we’ve got your back.
Luckily, we’ve been there and done that. In fact, it was those very awkward first date moments that inspired us to create a list of good questions to get to know someone. And they’re all interesting and fun to talk about. They’ll also help you get to know your date, leading the conversation into a more intimate and personal direction.
While most of our suggestions aren’t super heavy, weighted questions — and it’s probably good to avoid something too deep in the early going, anyway — they never fail to jumpstart a conversation. If you want to pique the interest of your date, these questions are foolproof and will give you great insight into who he or she is.
The Best Questions to Ask to Get to Know Someone
Let’s take a look at our top question recommendations for getting to know someone you’re interested in:
1. Who is the most important person in your life?
If family is important to you, this is a great question to ask. Learning who is close to your date’s heart can shed a lot of light on how he or she values relationships. And, if you’re looking for something long-term, knowing how your date feels about his or her own family will let you know what you’re in for if you stay together.
While this might be an odd question to ask out of the blue, it’s easy to work into the conversation, and a good question to ask to get to know her, especially if you start the ball rolling by saying who you’re closest to.
When you're going through this list think about if and how you've asked these questions in the past. A lot of guys out there who struggle to figure out why they can't get a girlfriend aren't self-reflective. If you don't regularly consider your current behavior and how to change it you won't make any progress.
2. If you ruled the world, what would you change?
This is a question that can lead to a fun and light-hearted chat or launch you into a deep discussion about the issues that are near and dear to both of your hearts. Either way, this question can really help you get to know how your date looks at the world.
Does he have a good grasp on current events? Is she interested and informed on hot button topics? Is your date fun, imaginitive and enjoys joking around?
Whether he or she responds seriously, jokingly or a mixture of both, you’ll be able to get a good handle on your date’s personality.
3. If you won the lottery, what are the first things you’d do with your money?
There’s no better question to ask if you want to learn what your date values. Is he all about his wants and needs? Is she focused on living the high life or helping others?
Your date’s answer will give you a pretty good idea if he or she is self-absorbed or is thoughtful and generous. If your date focuses only on buying amazing things for herself, chances are, she won’t be giving and considerate in relationships either.
This question can also be funny and may reveal if your date has a playful and imaginative side by coming up with wild and wonderful ideas, leading to further discussion on dreams and ambitions.
4. The rephrased question to know about their passions: How do you spend your free time?
Not everyone has hobbies or something they’d consider a true passion. That can make this question easier to answer than the typical “what are your hobbies or passions?”
Keeping your questions low-pressure makes it more likely you’ll get a good answer. It can also help you avoid awkward pauses where your date is fruitlessly wracking their brain trying to come up with something interesting.
This will also give you a good picture of what their day-to-day life is like.
5. If you never had to sleep, what would you do with the extra time?
While you’re on the topic of free time, this is a good question to sneak in. Not everyone has time to do all of the things they’d like. So this question gives your date a chance to talk about something they’ve always wanted to do.
Just like learning how your date spends their free time, the answer to this question can give you a pretty good idea if you have much in common.
Most of the questions on this list are also great when you're texting a girl for the first time or early in your relationship. Don't be afraid to use them offline and online.
6. What would you most want people to remember you for?
This is another one of those questions that can go either way. It can lead to a lot of laughter or to a very serious discussion about one another’s priorities.
Does your date want to be remembered for being successful at work, for being part of a loving family or for being a volunteer or philanthropist? Or maybe your date will come up with something off the wall like holding the world record for standing on one foot. Who knows?
One thing is sure: this is a good question to ask if you want to spark a great conversation. It also gives you more insight into your date’s personality and value system. It can also give you ideas about sweet things to say to her.
7. The question to know if you're compatible: What are your biggest pet peeves in a partner?
Everyone has things that drive them nuts, whether it’s showing up late or texting at the dinner table.
Knowing what your date doesn’t like can help you determine just how compatible you are. If, for instance, your date can’t stand lack of spontaneity and you always plan everything down to the last detail, you might not mesh very well in the long run.
This is one of the best ways to discover how much or how little you have in common and if you’re willing to compromise.
8. If you could change one thing about your life, what would it be?
This is a question that really allows your date to think big. Maybe it would be landing a dream job or owning a home mortgage-free. Maybe it would be a wish to see family more often or perhaps the ability to eat anything without gaining weight.
Whatever your date comes up with, it will give you a good idea of their values, of course. But it also shows you how self-assured they are. If your date talks about being better looking or more popular, it’s probably a sign of insecurity, shallowness or both. Likewise, if the preferred change is being rid of debt, your date is likely responsible and goal-oriented. Listen carefully to what your date has to say. This is a great question to ask to get to know someone and to learn how compatible you’d be.
9. What’s the worst date you’ve ever been on?
Although this isn't a question to ask if your evening isn’t going well, it can be a lot of fun! It will show you how forthcoming your date can be when a date is successful.
It can lead to some really hilarious stories about past experiences. This question can also create a bond between you as being fellow sufferers in the dating trenches. As a bonus, it will get your date thinking about how much fun they're having with you. This also can turn into a flirty question if the date has been fun so far.
This is an especially fun one when you're meeting and attracting girls on Tinder. Everyone who's used it has some horror stories and they're fun to share!
10. What’s the worst pickup line someone has used on you?
This question will flow naturally from the worst date query and can also lead to some hilarious stories as you swap “war” stories about pushy or lecherous comments you’ve received in the past.
Not only will you compare favorably to some of the awful encounters your date has had previously, but this can also lead to some really flirty banter. Talking about what cheesy pickup lines you’d use on each other, for instance, can add to the laughs while also intensifying the attraction between you.
Good Questions to Get to Know Someone Will Bring You Closer
So the next time you’re with someone you like, don’t panic if you run out of things to say. Keep these great questions to ask to get to know someone in mind. They will not only help you to break the silence, but it will also help you get to know your date. Sure, there’s always a chance you’ll discover you don’t have much in common. But if there’s chemistry between you, these easy conversation starters will enhance your connection. You might also learn just how compatible you are!
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