What is the most interesting question you can ask to get to know someone?
Last Updated: 29.06.2025 00:13
52~ Are you willing to make “those types” of bets with your partner?
38~ Share your most embarrassing sexual memory?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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What do you dislike about me? I asked you to be 100% honest.
64~ When was your very first orgasm? When was your first from having sex? Care to share?
1~ How old were you when you had your first kiss? Who? Care to Share?
Have husbands and wives ever had a threesome with someone in real life? How did it happen?
9- If you could have three wishes, what would they be? Why?
Get this wrong and this could mean the end… :-) some funny, some not…
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
20- What’s your favorite candy? What’s your least favorite?
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Do you watch it? What is your favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
17- What’s your favorite holiday? What’s your least favorite?
Why do the majority of feminists hate men (not all feminists)?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
71~ Would you give your partner a hand or foot job? Would you receive one?
5~ When you first started having sex, was it what you thought it would be?
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75~ If your partner wants an orgasm/have sex when you don't desire to have sex, how do you plan to deal with their needs?
Model/Photographer Police/Criminal
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
22- Do you have any birth marks? How about scars? Care to share how you got them?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What is your favorite toy? Ever wanted to try a specific toy?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Why did Britain steal Gibraltar from Spain?
45~ How do you feel about me blindfolding you? How about blindfolding me?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Does a person with schizophrenia hear voices?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
11- List at least 5 things on your bucket list. Have you done any of them already?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
How does gut health affect mental well-being?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
44~ Care to share something about yourself that no one else knows about you?
That one or two things that made you go hmmmm, OMG or wow!
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
15~ Have you ever been “in love”? Who? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
Nothing too Serious
23- What is your dream job? What was it as a child?
3- Should Pluto still be considered a planet? 4- How about smoking?
36- Do you play video games? What is your favorite? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
7-What do I do in bed that drives you wild? How about, what turns you off?
If you win, what will you make them do?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
18~ Who/when was your first “crush”?
21~ What was the best date you ever went on? What has been the worst?
If you say it, I will stop, and we can talk about it when you are ready.
82~ Do you have any fantasies involving Role-Playing?
What is your view on sex? Meaning, When/Where/ How often/
50~ How many children do you have? What are their ages?
Escort/Client Job Applicant/Hiring Manager
Nurse/Patient Celebrity/Fan
9- What’s your favorite season and why? What’s your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
76~ Have you had a threesome? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
26~ What side of the bed do you sleep on?
14- Do you have a “Deal Breaker”, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
62~ Have you used adult toys?
If yes, what?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
61~ How willing would you be to try new sexual positions?
19~ Who/when was your first “heartbreak”?
10- List 5 of your top pet peeves.
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
13- How about having a certain hair cut/style?
Would you mind if your partner watched it? How about together vs alone?
2~ How old were you when you got to 2nd base? (Tongue kissing, breast feeling, or outside the clothes genital contact) Who? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
Would you ever want to be woken up with oral and/or intercourse?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
59~ Have/do you masturbate? How often? What do you use? (Toys, Phone sex, Erotica, Hard Core, shower/water, etc) Would you, while your partner watches?
32- What's your greatest talent? Can I see it right now?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
10~ How many dates are necessary before you to have sex with someone?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
How well do you know me? And some of your thoughts about me
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
19- What’s your favorite fairytale? What’s your least favorite?
Prisoner/Prison Guard Landlord/Tenant
What have you learned about yourself that you did not before this?
83~ How do you feel about Porn?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Any that are a turn off?
13- What is the craziest/scariest thing you've ever done?
3- What’s your favorite smell? Do you a least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would /have you ever given your partner a lap dance and Striptease?
65~ Describe the best orgasm you’ve ever had? Care to share?
29- How superstitious are you?
34~ Do you like the lights on or off during sex?
* Give a rating for each one (0-100)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
11~ Have you ever been caught by your parents or children or others while having sex?
52~ What are your hobbies?
You know that I will be 100% truthful, so ask.
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
40~ If you could go back in time, and relive your life, with the knowledge you have now, what age would you go back to and why?
Does the thought excite you? Care to share?
48~ Do you have any siblings? Are you close to your family?
These go from easy to answer, to OMG, you really want to know that?! to some serious thought. Take your time and have fun with this. The past is the past… it got you two here together…
24~ What are your expectations in a relationship? (I know a very big question, take your time)
22- What is your favorite childhood memory? What is your least favorite?
A comprehensive questionnaire, this should be a fun exercise to get to know each other. Try to give as much detail as possible when answering questions. You can go through this together and talk about each question or fill out the questionnaire as completely as you can and once you are done, go through each question together. If you have been together for a while, it is also fun to try to answer the questions for your partner. Remember this should be fun, so if you do not wish to answer a question you can “PASS” and not answer. Both should answer honestly and without judgement. (This is important, without judgement) I hope this helps you get closer and strengthens your relationship… You can learn a lot about the other person… and yourself…
18- How often do you drink alcohol? What is your favorite drink?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couples’ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETC…)
Family Relation Age Play
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Please share Did you stop?
Do you have a favorite? Is it ok if your partner does?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What would you say to prove to yourself that it was really you?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
89~ Do you like taking showers together?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
12- What is the weirdest thing you've ever eaten?
*** Questions about Relationships/Past ***
53~ How much can you tell me about the one thing you are most passionate about?
The Ice Breaker Questions
*** Deal Breaker Questions ***
17- Have you ever done drugs? Which ones? How often?
If NO, would you ever have one? Would it be with 2 men or 2 women?
85~ If you gave me a “free Pass” to have me do anything for one hour, what would you want me to do to you?
31- If given a chance to be immortal, would you take it? Why?
5- Have you ever been hypnotized? Would you allow yourself to be?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Do you think this brought you closer together?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
I would allow you to do it… What would you do to me?
23~ What do you believe is required to have a successful and healthy relationship? (This is important, take your time, and really think about this)
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
33- If you could visit any time period, when would you pick? Please explain why?
1- What’s your favorite animal? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
42~ What’s your biggest regret in life?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Do you like it when they show and tell you what they want?
37- Do you like your name? If you could change it, what would you change it too?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
84~ How do you feel about reading/listening to adult stories?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
*** What’s Your Favorite…? ***
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
1- What was your first impression of me? Has it changed?
What is your favorite position? Why?
47~ What would be your dream job and why?
25~ How do you feel about PDA? (Public Display of Affection)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Have you ever? Care to Share?
41~ What are you best at in bed? What do you think you are not so good at? Anything you want to get good at?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
33- Beach or Mountains? Or is there another place to like better?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Any that are a turn off?
What was the longest? What was the shortest?
29~ What are some things that turn you off? What is your biggest turn off?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
2- What’s your favorite color? Do you a least favorite?
How about if they talk dirty and/or call you names?
11- Is there something you would like me to do, in any area of our relationship that I have not done, or you want more of?
28- What are some things that people do that irritate you?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
8- What are your thoughts on politics?
30~ What's something unexpected that turns you on?
51~ Are you willing to play adult games with your partner?
Do you like the “69” position? Do you prefer to be on top or bottom?
9- Is there something you’ve always wanted to ask me but you’re afraid?
28~ What are some things that turn on? What is your biggest turn on?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
40~ What’s the weirdest place you’ve ever had sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Can you Deep Throat? Do you like the taste of yourself?
36~ What is your favorite time of day to have sex/make love?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
70~ Would/do you have/like anal sex?
21- What's your favorite way to spend a weekend or time off?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
9~ How many times over your lifetime do you think you have had sex so far?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
How many times do you think you have “made love”?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Would you allow me to clean every part of your body with my soapy hands and fingers?
51~ What tends to bring a smile to your face?
*** Random Questions ***
Master/Slave Boss/Maid
8- What's your favorite flavor of ice cream? Do you a least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
81~ Do you have any kinks and/or fetishes?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
85~ If I gave you a “Free Pass” for you to do anything to me for one hour, knowing that no matter what you did,
3- What Superhero or Superpower would you want to be/have?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
50~ Where would you like to be touched more? Do you have a place that you want to be touched, that no one has, or has only happened a couple times? How about less?
92~ Everyone needs a “safe” word. What is yours?
How old are you? Male or Female?
92~ Have you ever had or have an STD? How many? What was it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
6- Do you have dreams? Can you remember them? What do you usually dream about?
49~ How many times have you been married? Why did they end?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Doctor/Nurse Stripper/Client
What’s the longest time you gone without having sex, after, having it? How much time between the others?
How many partners have you had oral sex with? Who? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
12- What’s your favorite food? What’s your least favorite?
10- What is your favorite family tradition? What’s your least favorite?
11- What's your favorite restaurant? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Repairman/Lonely Wife Virgin/Experienced
4- For a pet, Cat, dog or other?
Would you read them together?
Over time has your thoughts on sex changed?
7- What are your thoughts on religion? Is there an afterlife?
19- Do/have you smoked? What do you prefer? How often?
48~ Have you ever paid or been paid for sex?
What have you learned about me that was new and/or surprising?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
80~ Share your top three fantasies/desires. (Be detailed) 😊
*** Questions About Me ***
15- What bad habit do you wish you could quit? Do you have any addictions?
27- What was/ is nickname? Does it have a meaning behind it?
13~ Is there a difference between, making love, having sex, and fucking?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Teacher/Student Stranger/One Night Stand
14- What's your favorite dessert? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Would you do it again, and would you rather 2 females or 2 males?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
39~ What are your love languages?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…