Everything you could ever want to know about what questions to ask to get to know someone and connect is all in this article. Trust me, I’ve got you covered. This is the only resource you will ever need.
Have you ever been in a situation where you really wanted to impress and connect with someone, but were too nervous to think straight?
Did you end up fumbling over your words and replay the event in your mind later on?
No More Second Guessing Yourself
If this has ever happened to you, don’t worry—this article contains a list of 215 quality questions that act as “training wheels.”
This means, eventually, you won’t even need to think of this list because you’ll be so sure of yourself when in a conversation.
In fact, these questions and “training wheels” will set the foundation to guide your conversations for the rest of your life. Yes, even if you think you’re “bad” at connecting.
Don’t worry. You won’t have to do anything embarrassing or feel uncomfortable.
What’s Your Specific Situation?
I’ve separated the questions into categories to match your situation—why?
Depending on who you’re trying to get to know, your questions need to shift in tone and subject matter to align with the person and situation.
Frame of Reference Makes Or Breaks It
Getting to know someone requires knowing the right questions to ask in the right context and in the right “frame of reference”.
With that said, pick your situation, determine the level of connection you want to establish and choose from below. Or choose multiple categories if you want to be a good conversationalist in all ways.
Thanks to these categories, you don’t need to worry about screwing up or accidentally asking or saying the wrong thing at the wrong time!
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Table of Contents
- Icebreaker Questions To Get To Know Someone
- Mid Level Kind Of Personal Questions
- Very Personal Questions
- Questions To Ask Your Boyfriend
- Questions To Ask Your Crush
- Provocative Questions
- Professional Questions
Wipe the Slate Clean To Get Rid of “Awkward Silences”
One thing to point out is that you need to forget all other information you’ve heard or read about that give you tips on how to connect with others or how to have good conversations.
Truthfully, 99% of information out there is garbage that will sabotage you and make your conversations worse and causes awkward silences.
If you want to avoid awkward silences and effortlessly connect with others, “wipe the slate clean,” so to speak. Also, realize that having negative emotions in a conversation is a normal part of the human experience.
Being Nervous Is Normal
Yes, being nervous can happen. Especially when initially trying to connect with others. I’ll explain how to look at conversations in a way that’ll take away this fear and give you a brand new perspective to shape the conversations you have for rest of your life.
Don’t focus on trying to “be good at conversations;” just realize that your anxiety is normal and will pass as you gain “experiences.”
Now, with that said, here is the list of different categories of questions, your “training wheels.”
Icebreaker Questions To Get To Know Someone
- What’s your sign?
- Is your job fulfilling?
- Do you like being around lots of people or are you more of an “isolated”?
- Have you been to ____ insert random location?
- Do you come here often? (if at bar, for example, or music venue)
- What do you think of the music here? (if at concert, venue)
- Have you ever seen ___ insert classic famous movie?
- So, have you always been so ___ insert trait you observe about them? (for example, if they’re outgoing ask if they have always been so good with people. If shy and quiet, can say have they always been so mysterious. Don’t say “outgoing” or “shy” because can have negative connotation even though neither are “bad.”).
- What’s your dream job?
- If you had all the money in the world what would you do with your time?
- Are you a morning or night person?
- What was your favorite subject in school?
- Have you ever gone skydiving?
- Have you ever been on a serious diet?
- What is your favorite food?
- How often do you watch tv?
- What is your favorite tv show?
- What is your favorite movie?
- What’s your favorite song?
- What’s your least favorite song?
- Ever had severe food poisoning?
- Have you ever had surgery?
- Do you get bored easily?
- Are you good at analyzing people?
- Do you enjoy running?
- Do you enjoy fake or real Christmas trees? (if they celebrate Christmas)
- Favorite holiday?
- Do you like Halloween?
- Are you a dog or cat person?
- Have any pets?
- Do you like cities or small towns?
- Do you like roller coasters?
- Are you an adrenaline junkie?
- Do you like reading books?
- What’s your favorite website?
- Do you watch and read the news?
- Where do you see yourself in 5 years?
- What do you do for fun?
- Do you enjoy clubs/bars?
- Do you enjoy trying new food?
- What’s your favorite food?
- What’s your favorite restaurant?
- What is your least favorite food?
- Least favorite restaurant?
- Last time you went to a restaurant?
- Are you similar to your parents?
- As a kid, what did you want to be when you “grew up?”
- Were your parents strict?
- Did you ever get into fights with people as a kid?
- What were you like as a kid?
- What color hair did you have as a kid?
- Do you work out?
- How often do you workout?
Mid Level Kind Of Personal Questions
- Do you believe in soul mates?
- Have you ever been in love?
- Do you like being vulnerable or does it scare you?
- What is your family like?
- Are you an introvert or an extrovert?
- Do you enjoy nature?
- Have you ever been camping?
- What is your most embarrassing moment?
- Have you ever cheated on a test?
- What would you do if you had 24 hours to live?
- Favorite vacation?
- Have you ever been to a foreign county?
- What do your parents do?
- Do you have any “crazy” family members?
- What do you do for fun?
- Do you like drinking?
- Any crazy drunk stories?
- Do you have any brothers or sisters?
- Have you ever had any crazy relationship experiences?
- What’s the most pain you’ve ever been in?
- Have you ever broken a bone?
- Worst physical pain you’ve ever been in?
- Have you taken an iq test?
- Ever been in an ambulance?
- Have you ever dyed your hair?
- What’s more important love or money?
- If you could live forever, would you?
- How do you spend most of your time?
- Who is your role model, if anyone?
- Do you have a hero?
- Would you ever join the military?
- Do you believe love and hate are similar?
- Is all fair in love and war?
- If you had the power to rule the world what would you do?
- Favorite cologne?
- What is your #1 pet peeve?
- Did you go to college? If so, which?
- What subject did you enjoy most in school?
- Have you changed a lot over the years?
- Have you ever shocked yourself?
- What’s the craziest thing you’ve ever done?
- Do you lie about anything all the time?
- Can you tell me 5 things you like about yourself?
- Do you think you are a judgmental person?
- Do you think you’re self-sabotaging?
- What gives your life purpose?
- What do you feel strongly about?
- What’s the most important lesson you’ve learned?
- Do you have any kids?
- Do you like video games?
- How do you deal with stress?
- If you go go back in time what would you change?
- Best advice you’ve ever gotten?
- Are you happy with yourself?
Very Personal Questions
- If you don’t mind my asking… what’s your most traumatic memory from childhood?
- Do you think your past has shaped who you are?
- What is your #1 fear?
- Based on your #1 fear, do you do anything out of the ordinary in order to avoid it?
- How do you feel? Like, really feel?
- Do you love yourself?
- What’s your #1 “turn on?”
- Is there anything weird about you that you would never tell anyone?
- What is a really odd secret about you that you normally don’t share?
- Is it scary for you to be in love?
- Ever cheated on someone?
- How often do you lie? I know, odd question but I am just wondering.
- Do you have faith in humanity?
- Have you ever cried from a movie?
- Do any songs make you cry?
- Where would you want to live if you could live anywhere?
- Have you ever been in true love?
- Do you think women or men are nicer?
- How long does it normally take for you to be fully “yourself” around someone?
- Favorite memory?
- Have you ever loved someone “too much?”
- Do you have any “addiction?”
- Do you have an “addictive personality?”
- Are you an extremist?
- What is your deepest insecurity?
- What makes you angry?
- Is there anything about yourself you want to improve? If so, what?
- If you died tomorrow would you be ok with yourself?
- Do you enjoy “random hooking up?”
- Have you ever broken the law?
- If you could change one thing about yourself what would it be?
- Do you have any regrets in life?
- Do you like politics?
- How do you deal with pain?
- What’s the longest relationship you’ve been in?
- How long do you take to get ready in the morning?
- Have you ever been to a psychologist?
- Have you ever been to a psychiatrist?
- Do you ever have anxiety?
- Have you ever felt completely alone?
- Do you have any weird phobias?
- Have you ever punched someone?
- Biggest lie you’ve told?
- Ever been suspended in school?
- What’s the most trouble you’ve ever been in?
- Have you known anyone close who has passed away? (note: this is super personal)
- What do you want to do with the rest of your life?
- Do you wonder what happens when we die?
- Do you believe in life after death?
- Last time you wanted to punch someone?
- What are your views on religion?
- How often do you workout?
- Is it odd for you to be in a relationship or do you like being in one?
- Have you ever felt like you were losing your mind? If so, why?
Questions to Ask Your Boyfriend
- Do you think we will always be friends even if we weren’t together? I think we would be
- Do you remember when you realized you loved me?
- Do you know how much I appreciate you?
- What’s your passion in life?
- What’s the best moment of your life?
- Do you know that you’re amazing for who you are? I’m serious.
- Do you think it’s possible to be so open with someone?
- What made you who you are today? Like, is there anything you’ve gone through or experienced that shaped who you are right now that pops out?
- What matters most to you?
- Do you think jealousy is annoying?
- What is your favorite thing about women?
- Do you think women are slightly insane?
Questions to Ask Your Crush
- What do you do for fun?
- Can we please do something wild together?
- Do you like sports?
- Favorite sports team?
- Favorite porn? (Note: only if you know them well and things have gotten to that point)
- Do you have a temper? (Say so jokingly)
- Do you want to watch a movie together?
- Do you watch porn?
- Biggest turn on?
- Biggest turn off?
- Do you like being “in control?”
- Do you like being “controlled?”
- Is it weird if a woman is “in charge?”
- Hottest female celebrity?
- What do you like about porn if you watch it?
- Is it a turn off if a woman gets angry a lot?
- Ever had a wet dream?
- Tell me something crazy about yourself.
- What’s the craziest thing you’ve ever done sexually?
- Biggest fantasy?
- Have you ever “faked” it when hooking up? (You know what I mean!)
- Are you a boob or butt man?
- Do you have a super specific “type?”
- Blondes or brunettes?
- Do you enjoy random hooking up? Or are you a long term relationship person?
- Is there any “odd” turn on you have that you are embarrassed about? I don’t judge.
- Do you enjoy working here?
- How often would I be expected to ____ ?
- How should I approach ____ (insert tricky situation you feel confused about?)
- Do you need me to do anything else? (be a problem solver)
- Thank you for your time. Do you want me to do x, y, z this way or is there something else you had in mind?
Tips: always be courteous, never assume anything, respect the person’s time and keep questions to a minimum unless you actually have a question.
Faking Interest Is Obvious
Do not ask random things to pretend you care. Asking questions you read online in a “how to be good at job interviews” list comes off as both very obvious and foolish.
Preparation Will Become Your Best Friend
Having genuine questions prepared because you did research in advance is different than asking random questions. Beforehand, take some time to research the person you will have the interview or business conversation with.
Don’t get lost in the research but do have some practical, basic knowledge about who they are and what the company does.
Consider Context Always
Are you an employee trying to get hired? If you’re interviewing someone, you’ll approach your conversation differently than if you’re trying to get hired. The main takeaway is that context is key in any conversation. Consider your “role” in the conversation and ask questions accordingly.
If you’re getting to know someone in your personal or romantic life, it’s not about impressing them, it’s about discovering them…
This mindset takes the pressure of both of you. Why? Because you’re letting things happen not trying to make something happen. There’s a crucial distinction between allowing things to progress naturally and trying to force things.
Don’t Try To Impress: It Makes Them Think Of You Less
Trying to force things means you’re trying to impress. Trying to impress is the exact opposite of what will impress anyone.
Your attention should be on the interaction, on the other person and on what they’re actually saying.
The opposite of the above is being caught up in your head trying to steer the conversation in a certain direction in order to “make something happen.”
Think about dancing. Pretend you have a room full of 20 men who are potential dance partners. You start dancing with one man, think he is the “one” and don’t want to let go of him. You try dancing together but can’t get yourselves in sync with each other.
Your bodies simply don’t move in a way that’s jiving; the rhythm is off. What should you do? Keep dancing with the same person and try to make it work? Learn dance moves that you think will fix your rhythm and make things magically align?
Or should you try dancing with new partners and see if you naturally align and make each other better?
Fear of Loss Makes You “Force” Things
By being afraid to lose a dance partner, you waste time trying to be on the same wavelength rather than opening your life up for people who you effortlessly connect with.
Trying to talk to someone and poke at them until you “finally get to know them” isn’t going to work. Nothing you do or say will make someone “in line” with you.
Focus your attention and time on connections that are a good fit. Not every person is a natural fit.
Consider this: you’ve met hundreds of people in your life, maybe even thousands. And while many of them might have been nice people, how many became your best friends? Very few, right?
And there’s nothing wrong with that… even though you met many nice people, for whatever reason, you and those other people didn’t line up in that special way that made you both say, “Wow, I really enjoy this person. We ‘get’ each other, connecting with them and understanding them comes naturally.”
So keep that in mind when it comes to meeting people… in the same way that not everyone you meet will become your best friend, not everyone you meet will be a great match for you… and that’s completely ok!
It’s not about you personally or them personally… it’s about the match up, and some people match up better with each other. Again, there’s nothing wrong with this and when you realize nobody is to blame, you can let go of taking anything personally and just have fun discovering the other person .
Remembering that will take a lot of pressure off!
Don’t Take It Personally
Don’t take it personally if you’re out of sync with someone.
You have to sift through lots of people, so when you realize you’re looking for someone where the conversation comes naturally and is fun, you won’t waste time and effort trying to force conversations to work… you’ll have a fun carefree attitude, which will actually make conversations flow much more easily!
General Rule To Follow
With that said (how important context is), there are some general “best practices” to follow to be a good conversationalist.
I’m going to give you three general things to consider that matter most when it comes to asking questions in a conversation.
#1: Amount Of Time You’ve Known Someone
#2: How Well You Want To Get To Know Someone
#3: How Vested Are You In The Outcome
#1: Amount of Time You’ve Known Someone
If you know someone very well, you probably know a lot about their history, views, etc. This makes it easier to say things in a way that won’t offend them or make them uncomfortable.
One guaranteed way to make someone uncomfortable is to make an assumption about them when you hardly know them. So if you don’t know a person well, don’t just ask things in a way that could possibly make them feel judged.
For example, if a person is part of a book club and you’re mocking book clubs what do you think they’re going to feel? It was an innocent comment that you happened to mock book clubs but this one innocent comment ends up taunting how they view you.
And it’s not because they hate you or because you’re “bad” but rather because they think you think they’re bad and put up their own defenses.
#2: How Well You Want to Get to Know Someone
Think about how much you want to share and how much you even feel comfortable sharing. What is the intimacy level you’re trying to establish? Do you want to have a professional relationship? A close friendship? A relationship? Friends with benefits? This matters because your questions will be the most “effective” when in line with how well you want to get to know someone.
#3: How Vested You Are in the Outcome
All this means is can you take a risk or is it a situation where you have to save face and make sure you’re perceived as “normal?” (for example, work situation or a relationship with a professor or even a partner you’re in a relationship with…)
The more you care the more you’re risking. The less you care, the more you can risk.
Remember This No Matter What!
Regardless, your best bet is to always be engaged in the present moment. Interact with the person and listen to what they say and sometimes pay attention to what they don’t say.
Don’t just ask questions without considering what they just said. I cannot stress this enough.
If you took one thing away from this entire article it would be… be present and base what you say on what the person just said beforehand as well as what you know about the person.
When you ask them follow up questions, what happens is you discover more and more about the person. The conversation topics move around as you discover more about each other.
Getting to know someone is about the mutual interaction not the one-way question asking.
Once you realize that getting to know someone is a mutual process that happens in real time with another person this process won’t be scary.
What You Can Expect Going Forward
You’ll eventually feel comfortable no matter what situation you’re in. Even if you’re anxious, you’ll be comfortable with your anxiety.
New habits are easier to create than trying to change old habits. Try to create a new habit of being present in the moment. Over time, you will rack of positive experiences. These positive experiences will shift your perspective about yourself and your “skill” at connecting with others.
Trust me on this one. I’ve tested major boundaries and said things you’d honestly cringe at. My results showed me what consistently creates a set of conditions that foster connections.
You will absolutely be fine, more than fine.
Finally, remember to always have fun!!! I mean, unless you’re trying to get a surgical internship at a serious hospital or trying to land a brand new job… in that case, prepare! Preparation will be your best friend.
One last thing:
We have more questions for getting to know someone:
Want to find out if he really likes you? Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…