375 Questions Everyone Should Ask Their Lover
In this article you find personal teaching tales and 375 intimacy boosting questions to help you bring your relationship to the next level.
“This is all there is to it?”
This was the first thought that was popping up in my mind after I lost my virginity.
In the summer of 2005, I was waiting nervously for my blind date in the middle of Planten and Bloomen, a park in the city where I was born – Hamburg.
After my friends discovered that I was the last one of the squad who didn’t get laid yet, they decided it was a good idea to arrange a blind date for me with who they called “the easiest girl in the neighborhood”.
After the 180th homosexuality roast from my buddies, I decided that I should just get it over with…
I agreed to the blind date.
So there I was, a tall, skinny kid with horrible skin waiting nervously on a park bench for my first date ever to show herself.
While sitting there I became so paranoid about having bad breath that I ate 76 bubble gums which resulted in me having a stomach ache during the entirety of the date.
After what felt like an eternity, my date appeared, much to my surprise – she didn’t look that bad.
While talking we discovered that we had exactly three things in common: we both hated school, our parents and we wanted to get out of Germany at the very first possibility.
After exchanging meaningless teenager complains she looked at me with concern:
“Are you sick? Why are you sweating so much?”
I told her that I just finished a workout right before meeting her and my body was still in athlete mode, this of course was a lie.
The real reason why I was sweating like pig was that I was wearing two thick sweatshirts under my oversized business shirt in order to appear more muscular.
She believed me and sighed and pulled out a lollipop and put it in her mouth and said to me:
” Wanna try?”
I nodded, but instead of giving me the lollipop, she gave me the first kiss of my life.
After two minutes of making out, she pulled up her skirt, moved on top of me and we started to have sex, right there – in the fcking park, in the middle of the fucking day.
I was a deer in the headlight, didn’t know what to do, where to put my hands, what to do with my tongue or any other part of my body.
I was grateful that at least one of us knew what they were doing.
I closed my eyes as I was nearing my climax when suddenly I heard a scream:
An old female jogger discovered us and yelled as if she just witnessed a murder scene.
As we saw the jogger pick out her phone in order to call the police my date pulled her skirt up in a panic, pushed me away, and just took off.
To this day, I never saw a girl give a better Usain Bolt impression than my date on that day.
Instinctively, I followed her example and ran away too, or at least I tried.
Since my trousers were still at my shackles I fell into the nearest bush and hurt my family treasures in the process.
It took me a minute to gather myself, pull up my pants, and runoff for good.
As you can imagine, this was the end of my date, and I never saw her again.
I expected to feel like a real man after my first sexual encounter, but to be honest, the dominant feeling in my chest was disenchantment.
If this was all there was to this “love thing” it definitively did not deserve any kind of investment from my part (this was at least what I learned from my first few encounters).
I internalized through that experience that in order to fuse with somebody all I had to do was to show up and ask for it.
Shortly after my first time, I discovered happily that there are several online dating apps that enabled me to consume as many human beings as I wanted.
Even though I felt excitement at the beginning of my dating marathon, I realized that with each date I became colder, less sensible, and less me.
If you’ve ever been a serial datist, you know what this feels like.
Going through the motions, having the same conversations over and over again, and playing the same inauthentic role until you are sick of yourself and of anybody else.
My first relationships came and I brought with me what my ex called “a shit ton of baggage”.
One of the psychological fossils of my compulsive dating phase was the idea that “I have options”.
Once the honeymoon phases were over with my partners I remembered that I really don’t have to be in a relationship, I can just see many people at once and leave the relationship once it becomes work.
I thought my plan was genius, being a cool traveling bachelor for the rest of my life.
This was for years my personal utopia.
It took my years to realize that my happiness formula was off by a mile…
After a decade of tindering around the word and getting wasted on every continent, I received a phone call that would change my life and my idea of utopia forever; my father called me and delivered me the news that he had an incurable heart disease.
I was devastated, my most favorite human was about to be taken away from me.
Instead of playing chess with him at the park, we now played chess in the emergency station.
During that time, we had a series of brutally honest father-son conversations about life, regret, and of course – about love.
I asked him what the happiest times of his life were and he surprised me by telling me:
The best times were the ones I took for granted son.
He did not tell me about the many moments where he had business successes, the millions he made, he also did not speak about his legendary travel tales – he spoke of moments that to me honestly, sounded quite boring.
Moments where my mother and him were still together, moments where he and I played cards, moments where he returned home from work and he could light himself a cigar knowingly that everything is as it’s supposed to be.
Our father and son talks were always interrupted by a blond woman with wild hair who wore even wilder hats – Heike, the wife of my father.
Heike got up every morning at 6.00 and stayed till 22.00 at night in the hospital of my father, always providing us with humor and unlimited snacks.
Normally relatives were only allowed to visit their loved ones from 12.00 -16.00 but every nurse and every doctor in that hospital could see from a mile away that the term “visiting hours” did not apply to Heike.
She simply did not give a fuck about them, all she cared about was that her husband was sick and that he needed her.
Seeing this woman hold the hand of my father in times of ultimate suffering changed me.
The level of valor, resiliency, compassion, and optimism that this woman displayed while accompanying my father on his last steps taught me that with the right kind of person at your side, all ordeals of life become bearable – yes, even death.
After leaving the hospital I walked to the nearest train station and just sat there for hours and contemplated my own values.
I asked myself the same question that I asked my father: What were the happiest moments of my life?
I closed my eyes and missed one train after another.
As I was playing my life’s highlight mixtape inside my head again and again I realized that none of my most cherished moments revolved around what I did but who I did them with.
It was a perplex sensation, up to that point I viewed love as a prison that would prevent me from being me.
After those weeks of conversing with my father, I understood that real love is real and that it’s worth fighting for.
But how do you know if the one in front of you has the potential to be your partner in crime…
The word intimacy is derived from the Latin intimatio, which means to “make known”.
In order to experience something real with your partner, it’s important that you, once the episode of blind idealization ends make a conscious effort to “make yourself known” to whoever you are dating.
When we fall in love with somebody we literally have a visual sickness that makes all the flaws of the other person invisible and all their virtues conspicuous.
As long as you are freshly in love you have no fcking idea who you are dating because you are riding a colossal wave of hormonal ectasia.
I made the mistake for years to end relationships every time I reached what I call the “Stage Of Coldness”.
Most couples break up at this point because they realize that their partner is not perfect, they discover that it’s easier to just go back to seeing other people again because having new things feels better in the short run; but let me tell you something weird that I learned over the years – behind this pain line is where all the good shit happens.
Blissful normality occurs once you look at a human being with all their flaws, mistakes, insufficiencies, emotional baggage, and still decide that they are perfect.
Maybe not perfect in common sense, but you feel in your chest that they have the potential to be perfect for you.
Forging an intimate alliance with somebody is a two-way street.
It requires patience, curiosity, the willingness to change, and most importantly – a heart that isn’t afraid of the light of life.
Below you will find hundreds of questions that you could ask your partner, date or affair so you can learn who you are really seeing and in order to “make yourself known” to the person in front of you so that you an discover together if you both have the potential to be an ideal match.
375 Questions Everyone Should Ask Their Lover
- What was growing up like for you?
- When you think of the phrase “perfect day“, what comes to mind? Why?
- Who is your longest-standing friend you are most proud of?
- What’s your favorite word
- Do you find it easy to make friends and build relationships?
- How do you handle having a bad day?
- What are your weekend mornings like?
- What are your values?
- How would you describe the relationship you have with yourself?
- Are you afraid of confrontations?
- What does love mean to you?
- What’s the biggest lie you tell yourself and others about yourself?
- What was your first kiss like?
- What got you attracted to me?
- What is your definition of romance?
- What’s your favorite book?
- What’s your favorite Tv show?
- Do you see yourself as being competitive in nature?
- Are you an intro or extrovert?
- Where would you like to live one day?
- If you could have it your way, what would an ideal relationship look like to you?
- Do you have any fears about your future?
- Are you adventurous? If so, how?
- What do you hope never changes?
- What songs have you completely memorized?
- What job would you be terrible at?
- What would you rate 10 / 10?
- What are you absolutely determined to do?
- What quirks do you have?
- What would your perfect room look like?
- What website do you visit most often?
- What age do you want to live to?
- What movie title best describes your life?
- Are you usually early or late?
- What skill would you like to master?
- What kind of art do you enjoy most?
- What takes up too much of your time?
- What do you wish you knew more about?
- What’s the best way to start the day?
- What mystery do you wish you knew the answer to?
- How different was your life one year ago?
- What’s the best single day on the calendar?
- What are some things you’ve had to unlearn?
- What’s your favorite genre of book or movie?
- What’s the farthest you’ve ever been from home?
- What TV or YouTube channel doesn’t exist but really should?
- Where is the most interesting place you’ve been?
- What fad or trend do you hope comes back?
- What city would you most like to live in?
- When was the last time you climbed a tree just for fun?
- What do you consider to be your best find?
- What is special about the place you grew up?
- What age do you wish you could permanently be?
- What’s worth spending more on to get the best?
- What are you most likely to become famous for?
- What fictional place would you most like to go?
- Where is the most relaxing place you’ve ever been to?
- What have you only recently formed an opinion about?
- What is the most heartwarming thing you’ve ever seen?
- What’s the most interesting piece of art you’ve seen?
- What’s something you like to do the old-fashioned way?
- Would you rather go hang gliding or whitewater rafting?
- Who has impressed you most with what they’ve accomplished?
- How do you relax after a hard day of work?
- What popular TV show or movie do you refuse to watch?
- What job do you think you’d be really good at?
- What pets did you have while you were growing up?
- Where would you spend all your time if you could?
- What would be the most amazing adventure to go on?
- What would be your ideal way to spend the weekend?
- What’s the best way a person can spend their time?
- What one thing do you really want but can’t afford yet?
- What is the luckiest thing that has happened to you?
- What are some small things that make your day better?
- What’s the best thing that happened to you last week?
- What are you looking forward to in the coming months?
- What’s your favorite piece of clothing you own/owned?
- What is the most annoying habit that other people have?
- What game or movie universe would you most like to live in?
- What is the most impressive thing you know how to do?
- What was the best book or series that you’ve ever read?
- What question would you most like to know the answer to?
- What are you interested in that most people haven’t heard of?
- Why did you decide to do the work you are doing now?
- What state or country do you never want to go back to?
- Where do you usually go when you have time off?
- What are you most looking forward to in the next 10 years?
- What is the most annoying question that people ask you regularly?
- If you suddenly became a master at woodworking, what would you make?
- What could you give a 40-minute presentation on with absolutely no preparation?
- What amazing thing did you do that no one was around to see?
- What hobby would you get into if time and money weren’t an issue?
- If you didn’t have to sleep, what would you do with the extra time?
- When people come to you for help, what do they usually want help with?
- What is something you think everyone should do at least once in their lives?
- What’s something you’ve been meaning to try but just haven’t gotten around to it?
- If all jobs had the same pay and hours, what job would you like to have?
- Who’s your go-to band or artist when you can’t decide on something to listen to?
- If you were dictator of a small island nation, what crazy dictator stuff would you do?
- What is something that most people consider to be a luxury, but you don’t think you could live without?
- What would be your first question after waking up from being cryogenically frozen for 100 years?
- What is something that a ton of people are obsessed with, but you just don’t get the point of?
- If you could turn any activity into an Olympic sport, what would you have a good chance at winning a medal for?
- What piece of entertainment do you wish you could erase from your mind so that you could experience it for the first time again?
- If you had unlimited funds to build a house that you would live in for the rest of your life, what would the finished house be like?
- What gets you fired up?
- What makes a good life?
- What risks are worth taking?
- What do you take for granted?
- Who inspires you to be better?
- What do you have doubts about?
- What are your weak spots and trigger points?
- When do you feel truly “alive”?
- What fact are you resigned to?
- What book impacted you the most?
- What’s the best thing about you?
- What would a mirror opposite of yourself be like?
- What irrational fear do you have?
- What would be your spirit animal?
- What would be the scariest monster you could imagine?
- What’s the hardest lesson you’ve learned?
- What’s something you are self-conscious about?
- What is one or two of your favorite smells?
- Have you ever given to any charities?
- What’s the last adventure you went on?
- What was the most memorable gift you’ve received?
- What chapters would you separate your autobiography into?
- What do you hope your last words will be?
- What do you spend the most time thinking about?
- What is something you can never seem to finish?
- What mistake do you keep making again and again?
- What’s the best thing you got from your parents?
- What is the strangest thing you have come across?
- If you could make a 20-second phone call to yourself at any point in your life present or future, when would you call and what would you say?
- What’s the best and worst thing about getting older?
- If you could have a never-ending candle that smelled like anything you wanted, what fragrance would you want it to be?
- What is something you are certain you’ll never experience?
- What challenging thing are you working through these days?
- What’s one responsibility you really wish you didn’t have?
- What are three interesting facts about you?
- What was the best compliment you’ve received?
- What chance encounter changed your life forever?
- What do you want your epitaph to be?
- What are you really good at, but kind of embarrassed that you are good at it?
- What is the “Holy Grail” of your life?
- What do you like most about your family?
- What do people think is weird about you?
- What is something you will NEVER do again?
- Who is/was your most interesting friend?
- What are you most likely very wrong about?
- What’s the most immature thing that you do?
- What stereotype do you completely live up to?
- What is the biggest lesson you NEVER learned?
- What dumb accomplishment are you most proud of?
- What do you wish your brain was better at doing?
- If your childhood had a smell, what would it be?
- In your group of friends, what role do you play?
- Which of your scars has the best story behind it?
- What have you created that you are most proud of?
- What do you strongly suspect but have no proof of?
- What were some of the turning points in your life?
- What bends your mind every time you think about it?
- What’s the title of the current chapter of your life?
- Among your friends or family, what are you famous for?
- What is something that your friends wouldn’t believe was true about you?
- What’s something horrible that everyone should try at least once?
- If you had a personal flag, what would be on it?
- If your life was a book, what would its title be?
- As the only human left on Earth, what would you do?
- What stats for your life would you most like to see?
- What did you think you would grow out of but haven’t?
- What are three of the most significant numbers in your life?
- What are some of your personal “rules” that you never break?
- What’s the best and worst piece of advice you’ve ever received?
- What song or artist do you like but rarely admit to liking?
- What annoys you most about the in-groups you are a part of?
- What small gesture from a stranger made a big impact on you?
- What do you regret not doing or starting when you were younger?
- What’s the dumbest thing you’ve done that actually turned out pretty well?
- If you had to change your name, what would you change it to?
- When people look at you, what do you think they see/think?
- What can you not get right, no matter how many times you try?
- What question can you ask to find out the most about a person?
- If you were put into solitary confinement for six months, what would you do to stay sane?
- If you could have a video of anyone event in your life, what event would you choose?
- What incredibly strong opinion or belief do you have that is completely unimportant in the grand scheme of things?
- What are the top three things you want to accomplish before you die? How close are you to accomplishing them?
- If you could convince everyone in the world to do one thing at one point in time, what would that thing be?
- If you had a clock that would countdown to any one event of your choosing, what event would you want it to countdown to?
- What do you wish you could tell yourself 10 years ago? What do you think you’ll want to tell your current self 10 years from now?
- If you were forced to relive one 10-minute block of your life again and again for all eternity, what 10 minutes of your life would you choose?
- Have you ever saved someone’s life?
- As you get older, what are you becoming more and more afraid of?
- What lifestyle change have you been meaning to make for a while now?
- In what situation or place would you feel the most out of place?
- There are two types of people in this world. What are the two types?
- What personality trait do you value most, and which do you dislike the most?
- When was the last time you changed your opinion/belief about something major?
- What would you do if you knew you were going to die in one day?
- What are some of the events in your life that made you who you are?
- If life is a game like some people say, what are some of the rules?
- They say that everyone has a book in them. What would your book be about?
- What could you do with two million dollars to impact the most amount of people?
- What would be some of the most annoying things about having yourself as a roommate?
- What do you want to be remembered for?
- If you could make one rule that everyone had to follow, what rule would you make?
- What’s something that happened or something that someone said that changed how you view the world?
- What are you addicted to?
- What keeps you up at night?
- What name would you give to our relationship if we were to name it after a movie?
- Why me?Why not someone else?
- What was the first thing you noticed about me?
- What’s the biggest dream you aim to achieve in your life?
- How long do you think this will last?
- Are you really ready to let me into your life?
- What specific behaviors and actions from me feel most loving to you?
- How can I ask for more love from you?
- Do you know who I am?
- How will I know if you need more love from me?
- What does unconditional love mean to you?
- What behavior changes do you need from me?
- What specific actions or words could I use to show you how much I respect you?
- What am I doing that makes you feel disrespected?
- How am I hurting you?
- What do you want for yourself in terms of love?
- Do you see me as a good listener?
- Can you be patient with me?
- How can I improve your life?
- What’s a dealbreaker for you in terms of our relationship?
- How can I express my love to you so that you can see that I’m in your corner of the ring fighting for you against the world?
- How can we have more intimate conversations?
- How can I respectfully tell you that I need time for myself?
- Is there anything about the language I use that bothers you?
- Are there topics that you can’t discuss with me?
- What topics do you love discussing with me?
- What are your emotional needs?
- What do you value in a relationship?
- What do you hate in a relationship?
- What should I say to you when I need more from you emotionally?
- What relationship do you have with yourself?
- To what degree are you in love with the worst of you?
- What’s the biggest lie you yourself about you?
- What part of your life is in need of repair?
- If you could only make our relationship better by subtraction, what part of us would you like to leave behind?
- Are you really ready to integrate me into your life? Do you want me to integrate you into mine?
- How much affection in public are you comfortable with?
- What activities and interests can we develop that will bring us closer together?
- Who do we know that has the kind of relationship that we would like to have?
- What can we learn from them?
- What will be our early warning signs that our relationship is in trouble?
- What are your deepest dreams for yourself and for us?
- How am I getting on your nerves? Any habits that drive you nuts?
- Do you have bad habits that you feel you must hide from me?
- What bad relationship habits do we have?
- Are we positive role models for the people around us?
- Are you comfortable with my hygiene and self-care? If not, what would better look like to you?
- What do I say that drives you nuts?
- What makes you feel heard and understood when we have a conflict?
- How can you best manage anger or frustration so we can talk calmly?
- In times of conflict, how can we avoid hurting each other linguistically?
- What are your deepest wounds from the past and how can I support you there?
- What flaw of yourself do you want me to accept?
- What will you not change for me or for yourself?
- How have your parents and their relationship impacted your expectations or needs in our relationship?
- Is there anything in your past that you are uncomfortable sharing with me? If so, how can I show you that you can tell me anything?
- What steps are you willing to take to heal from our past mistakes?
- How much time would you ideally like to spend with me?
- How much alone time do you need?
- How can I let you know that I need time for myself without hurting you?
- What do you need to hear from me right now?
- Do I have any friends you don’t feel comfortable around? If so, why?
- How often would you like to have double dates?
- What are your favorite group activities?
- Which of our friends could you see us traveling with?
- Do you feel jealous of any friendships? If so, why?
- How much time do you want me to spend with your family?
- How can I tell you respectfully that I want to spend less time with your extended family?
- How do we handle behavior, expectations, or demands that we don’t like from our extended family?
- Do you want to have children one day? If so, natural ones, or do you want to adopt? How many?
- What are your top five values?
- Where is our relationship consistent with your values? Where is it not?
- Do you meditate?
- How important is your spiritual life, how do you practice it?
- If we don’t share the same spiritual views, how is this impacting our relationship?
- What can we do together to create a healthier lifestyle?
- What can we specifically do to change our eating habits?
- How can I tell you gently that you are not taking good care of yourself?
- How do you want me to treat you when you are having a bad day?
- How can I ask you to work on a bad habit that I observe in you? Is there a way that I can do this without hurting you?
- If you could improve one thing related to your health and fitness, what would it be?
- How can I best support you in your career?
- How is your work affecting your overall happiness in your life? If so, how?
- Am I working too much?
- How much job security do you need?
- What do you want to do differently from your parents in terms of relationships?
- What are your long-term financial goals?
- What are your financial values?
- What are your financial beliefs?
- Do our spending habits align with our vision for our future?
- How should we handle it if we have a disagreement about money?
- How much money should we save each month?
- How have you reacted in the past to serious life problems such as losing your job, losing a relationship, or losing a loved one?
- What kind of past crisis helped you to become the awesome person that you are today?
- How do you cope with pain?
- Why do you love me?
- What lie do you tell most often?
- What do you regret not doing?
- What gives your life meaning?
- What are you most insecure about?
- What bridges do you NOT regret burning?
- What’s the most illegal thing you’ve done?
- How do you get in the way of your own success?
- What are you afraid people see when they look at you?
- What’s the most surprising self-realization you’ve had?
- How do you hope you’ll change as a person in the future?
- What’s one thing you did that you really wish you could go back and undo?
- What do you most often look down on people for? What do you think other people look down on you for?
- What turns you on?
- What turns you off?
- In an ideal world, how long would foreplay be?
- Is there a sexy scene from a movie that you want to recreate with me?
- If you had a pair of x-ray glasses, which part of my body would you look at first?
- What’s one thing you want me to do to you that I haven’t done?
- If we were in a public place, and I wanted to do it, what would you want me to do?
- What’s the farthest you’ve gone on a first date?
- My dear Lover, could you send me a dickpick?
- If you could only touch me in one place, where would it be?
- Where would you like me to touch you?
- What would an ideal sexual partner look like for you?
- What do you think about toys in the bedroom?
- What was the last dirty dream you had?
- What’s a naughty fantasy you haven’t yet tried?
- Do you prefer doing it in the morning or night?
- Rough or sensual?
- How often would you like to have sex?
- What was your first time like?
- Do you like sexting?
- What about cam sex?
- Have you ever done it in front of other people?
- Have you ever done it with more than one person in one day?
- Are you part of the mile-high club?
- Have you ever hooked up with someone you weren’t supposed to hook up with?
- Where’s the most uncomfortable place you’ve ever done it?
- Who do you think of when you pleasure yourself?
- What’s the longest you’ve gone without doing it?
- What is your favorite part of my body?
- You decide to give me a full body massage, where do you start?
- What’s an instant turn-on for you?
- What is one thing that I wear that you find completely irresistible?
- Can you give me a good example of your dirty talk?
- What is your favorite thing I do to you in bed?
- Do you like me being possessive over you?
- When you first met me, was it love at first sight?
- If you can describe my body with three words, how would you describe it?
- Do you prefer long hair or short hair?
- When do I look the most beautiful to you?
- If you were looking at movies online, what do you look for?
- Do you like your hair pulled?
- Have you ever done it in the backseat?
- Do you prefer top or bottom?
- Have you ever taken naked pictures of yourself?
- What kind of music do you like to play in the bedroom, if any?
- Do you like experimenting with different positions?
- Do you prefer having some fun in the morning or at night?
- Did you ever have a crush on a teacher?
- Would you say you’ve been on Santa’s naughty or nice list most?
- Did your parents ever give you the “birds and the bees” talk?
- What object did your adult-ed teacher use to demonstrate how to put on protection?
- Would you consider yourself romantic?
- What’s your ideal date night?
- What attempts did you make to woo me? Which ones worked?
- What do you think of open relationships?
- How old were you when you had for the first kiss?
- Has anyone accidentally seen you naked?
- When you’re on top, what’s your favorite position?
- When we wake up in the morning, what is the first thought that comes to mind when you look at me?
- Do you like cuddling?
- How many rounds do you think you could go?
- What’s something new you’d like to try in bed?
- Do you like going down on me?
- Do you like me going down on you?
- Have you ever done it outside?
- Have you ever cheated or been cheated on?
- What’s the best bedroom experience that you’ve ever had?
- Where is the most public place that you’ve touched yourself?
- Have you ever been attracted to someone of the same sex?
Shoutout to the brilliant sexual columnist Anni We for helping me with the gathering of the intimacy boosting questions.
I believe that the quality of our questions determines the quality of our life.
In the creation of this article, I spoke to hundreds of you guys and I received invaluable pieces of advice, rich pearls of wisdom, and helpful warnings.
I will cherish and contemplate every single conversation I had with you and I will do my best to teach others what I’ve learned in the course of our conversations.
You are fucking awesome.