101 Questions to Connect Deeply
(+ 20 Bonus Questions for Romantic Partners)
So often, we live on the surface level of connection. Out of fear of rejection, we avoid the deep, meaningful, potentially scary depths of communication that can shed light onto our shadow. These one hundred and one questions to spark deep intimacy between two humans. Note that they will only ‘work’ if you do: open up. Share the depths of your psyche, your most vulnerable truth. Living from that place generally doesn't scare people off like we think it may. In my experience, it actually gives permission to meet people in that place.
The first 101 are general questions for any romantic relationship (new, or long term). The bonus 20 are specifically tailored for two people who have been in a romantic relationship for some time already.
What was growing up like for you?
What is one of your best memories?
What is obstacle are you currently trying to overcome?
How are you, really?
Describe our relationship in one word.
What is the best compliment anyone has given you?
What is something that you are looking forward to?
How often do you talk to your parents/ siblings?
What is something that overwhelms you?
How would you define monogamy? / How would you define cheating?
Is love enough to make a romantic relationship work?
What is something that turns you on?
Are you a good cook? What’s your favourite thing to cook (or to eat)?
What is one of my biggest strengths, and one of my biggest weaknesses?
What was the most painful part of your childhood?
What do you hate about your current job, and is it enough to make you rethink your position there?
What are you secretly insecure about?
What motivates you?
What would you replicate and what would you change about your childhood, while raising your own children?
What is the last thing that made you cry?
What are your thoughts on vaccinations/ medical intervention?
What is health to you, and how important is it as a value?
Have you/ do you have any health challenges?
Is it ever ok to lie to a partner?
What is something that didn’t work out in your past, but in retrospect it was for the best?
What is one of your biggest fears when entering romantic relationships?
Finish the sentences: Strangers would describe me as:_________. But only I know that I am _________.
Describe your perfect day.
How do you feel about confrontation?
When is the last time you experienced confrontation, and how did you react?
What foods don’t you eat/ why?
Do you have any allergies?
Admit something.
What is your favourite smell?
Do you have any debt?
Who was your first love?
Have you/ would you go hunting?
What is the last lie that you told?
What are your thoughts on the organic movement/ organic food?
What question are you trying to answer in your life right now?
Are you afraid of failure?
What drives you more career wise: passion in your work, or income figure?
Have you ever cheated or been cheated on?
What do you think of online dating/ what has your experience been?
Are you a jealous person?
What’s the most pain in that you’ve been in that wasn’t physical?
Do you easily remember peoples names/ birthdays?
Who do you look up to?
Have you ever ended a relationship? Why and how did you go about it?
Do you own any pets/ would you like to own some in the future?
What are you trying to prove to yourself?
Thoughts on abortion?
What do you admire most about me?
Thoughts on marriage?
Have you been in a long term romantic relationship? How did it end?
Are you lying to yourself about something?
How do you react when you are angry?
How do you let off steam when you’re stressed out?
Do you think that your social media ‘you’ is authentic to the ‘real you’?
Can a relationship overcome infidelity?
What enables you to become vulnerable with someone?
Describe how you feel right now in one word.
How would you describe me to a stranger?
What are your thoughts on pornography?
Tell me about your first kiss.
What is my super power?
Do you believe in/ follow astrology?
Are you a virgin? If not, tell me about your first sexual experience.
Do you masturbate?
Have you ever faked an orgasm?
Favourite form of foreplay?
What has this conversation so far taught you about yourself?
Can you recommend me a book to read, based on this conversation?
What are your thoughts on open relationships/ polyamory?
Have you ever had a threesome?
Would you ever have a threesome (/again if you already have)?
What is something you haven’t tried sexually that you would like to?
Is there anything you don’t enjoy sexually? / Where are your boundaries?
What contraception method(s) do you use?
What is your relationship to sexual health/ STI checks?
What is your relationship to alcohol?
In what ways are we the same, in what way are we different?
Describe your sense of humour/ what makes you laugh?
What is the best present you’ve ever received?
Do you enjoy physical touch, in private and/ or in public?
What is something most people don’t know about you?
Have you ever had to end a friendship? Tell me about it.
What are your thoughts about stay-at-home mom/ dads?
Who do you think should pay for the first day, and why?
Thoughts about on sex on a first date?
Have you ever been trapped in an elevator?
Have you ever been robbed?
Tell me something about your father.
Tell me something about your mother.
Have you ever been accused of something that you are innocent of?
Describe your perfect vacation.
If we could take a plane anywhere in the world right now together, where would we go?
What is one of your recurring worries?
Do you swear?
Do you want children?
What is one of the first things you thought when we first met/ you first saw me?
20 BONUS QUESTIONS FOR THOSE ALREADY IN AN INTIMATE RELATIONSHIP
How can I be a better partner to you?
If you really knew me, you would know that… fill in the blank
Did I withhold anything from you today/ this week? (ask this question to yourself)
What has been on your mind lately, that you may have been afraid to open up about?
What part of our relationship do you miss (things we may have stopped doing over time)?
What is your biggest fear in our relationship?
What works in our relationship, and what hurts?
What is something that I do that turns you off/ pushes you away?
What is something I do that turns you on?
What is one of your favourite memories of us together?
What is something you would like to tell me, but haven’t?
Do you think we have a healthy relationship?
Fill in the blank: I get triggered when you: ________, because it reminds me of this aspect of my childhood: _____________.
How has our relationship evolved since the start?
Did you ever imagine we would be where we are now in our relationship?
Tell me something you value about the person that I am.
What is your favourite sexual memory together?
How do you think we can improve our sex life?
What is your favourite thing that I do for you?
How can I better support you?
