What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 13:25
45~ How do you feel about me blindfolding you? How about blindfolding me?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Do you like the “69” position? Do you prefer to be on top or bottom?
31- If given a chance to be immortal, would you take it? Why?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
You know that I will be 100% truthful, so ask.
If you say it, I will stop, and we can talk about it when you are ready.
61~ How willing would you be to try new sexual positions?
Escort/Client Job Applicant/Hiring Manager
76~ Have you had a threesome? Care to Share?
What have you learned about yourself that you did not before this?
How good do you sing and how do you know this?
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?
*** Deal Breaker Questions ***
Do you have a favorite? Is it ok if your partner does?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
*** Questions about Relationships/Past ***
Repairman/Lonely Wife Virgin/Experienced
Should parents force their kids to go to school when they are sick?
How many times do you think you have “made love”?
The Ice Breaker Questions
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
7- What are your thoughts on religion? Is there an afterlife?
7- What if a person smells a certain way? 8- How about smoking?
What is the best way to get over your ex?
20- What’s your favorite candy? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
82~ Do you have any fantasies involving Role-Playing?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
40~ What’s the weirdest place you’ve ever had sex?
37- Do you like your name? If you could change it, what would you change it too?
30~ What's something unexpected that turns you on?
Nothing too Serious
32- What's your greatest talent? Can I see it right now?
81~ Do you have any kinks and/or fetishes?
5~ When you first started having sex, was it what you thought it would be?
Is 1500 calories enough for a 5’3 15-year-old who is non-active?
29~ What are some things that turn you off? What is your biggest turn off?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
I gave him everything. He said he loved me. Why?
What have you learned about me that was new and/or surprising?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
21~ What was the best date you ever went on? What has been the worst?
What's the most incredible coincidence that ever happened to you?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
11~ Have you ever been caught by your parents or children or others while having sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
71~ Would you give your partner a hand or foot job? Would you receive one?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
22- What is your favorite childhood memory? What is your least favorite?
12- What is the weirdest thing you've ever eaten?
* Give a rating for each one (0-100)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
36- Do you play video games? What is your favorite? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What was the longest? What was the shortest?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Please share Did you stop?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Nurse/Patient Celebrity/Fan
17- What’s your favorite holiday? What’s your least favorite?
12- What’s your favorite food? What’s your least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Family Relation Age Play
Any that are a turn off?
Do you like it when they show and tell you what they want?
10- List 5 of your top pet peeves.
*** Questions About Me ***
48~ Do you have any siblings? Are you close to your family?
13- How about having a certain hair cut/style?
19- What’s your favorite fairytale? What’s your least favorite?
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?
Master/Slave Boss/Maid
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Does the thought excite you? Care to share?
Have you ever? Care to Share?
26~ What side of the bed do you sleep on?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
25~ How do you feel about PDA? (Public Display of Affection)
21- What's your favorite way to spend a weekend or time off?
50~ How many children do you have? What are their ages?
13- What is the craziest/scariest thing you've ever done?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What is your favorite position? Why?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
33- If you could visit any time period, when would you pick? Please explain why?
52~ Are you willing to make “those types” of bets with your partner?
I would allow you to do it… What would you do to me?
Over time has your thoughts on sex changed?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
9- Is there something you’ve always wanted to ask me but you’re afraid?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
*** What’s Your Favorite…? ***
51~ Are you willing to play adult games with your partner?
51~ What tends to bring a smile to your face?
42~ What’s your biggest regret in life?
19~ Who/when was your first “heartbreak”?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
If NO, would you ever have one? Would it be with 2 men or 2 women?
36~ What is your favorite time of day to have sex/make love?
Teacher/Student Stranger/One Night Stand
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
33- Beach or Mountains? Or is there another place to like better?
48~ Have you ever paid or been paid for sex?
That one or two things that made you go hmmmm, OMG or wow!
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?
What do you dislike about me? I asked you to be 100% honest.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How many partners have you had oral sex with? Who? Care to Share?
If you win, what will you make them do?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Get this wrong and this could mean the end… :-) some funny, some not…
(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…)
*** Random Questions ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Would you ever want to be woken up with oral and/or intercourse?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
38~ Share your most embarrassing sexual memory?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
39~ What are your love languages?
84~ How do you feel about reading/listening to adult stories?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
1- What’s your favorite animal? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Model/Photographer Police/Criminal
13~ Is there a difference between, making love, having sex, and fucking?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
60~ How important is oral sex? Do you like receiving? Do you like giving?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
1- What was your first impression of me? Has it changed?
14- What is an embarrassing moment in your life? How about your most embarrassing?
62~ Have you used adult toys?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
What is your view on sex? Meaning, When/Where/ How often/
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would you read them together?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
92~ Have you ever had or have an STD? How many? What was it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
9- If you could have three wishes, what would they be? Why?
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?
2- What’s your favorite color? Do you a least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
11- How about if they like a certain sports team? 12-How about drinking too much?
6- Do you have dreams? Can you remember them? What do you usually dream about?
9- What’s your favorite season and why? What’s your least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
28- What are some things that people do that irritate you?
Would you allow me to clean every part of your body with my soapy hands and fingers?
5- Have you ever been hypnotized? Would you allow yourself to be?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
What would you say to prove to yourself that it was really you?
Any that are a turn off?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
47~ What would be your dream job and why?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
92~ Everyone needs a “safe” word. What is yours?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
19- Do/have you smoked? What do you prefer? How often?
15- What's your favorite saying? What word or phrase is your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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,
13- What’s your favorite drink? What’s your least favorite?
10- What is your favorite family tradition? What’s your least favorite?
Do you think this brought you closer together?
8- What's your favorite flavor of ice cream? Do you a least favorite?
29- How superstitious are you?
53~ How much can you tell me about the one thing you are most passionate about?
89~ Do you like taking showers together?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you do it again, and would you rather 2 females or 2 males?
17- Have you ever done drugs? Which ones? How often?
52~ What are your hobbies?
Would you mind if your partner watched it? How about together vs alone?
15~ Have you ever been “in love”? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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…
How old are you? Male or Female?
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?
14- What's your favorite dessert? Do you a least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
22- Do you have any birth marks? How about scars? Care to share how you got them?
83~ How do you feel about Porn?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
70~ Would/do you have/like anal sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
How about if they talk dirty and/or call you names?
How well do you know me? And some of your thoughts about me
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Would /have you ever given your partner a lap dance and Striptease?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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…
49~ How many times have you been married? Why did they end?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
1~ How old were you when you had your first kiss? Who? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Doctor/Nurse Stripper/Client
Can you Deep Throat? Do you like the taste of yourself?
11- List at least 5 things on your bucket list. Have you done any of them already?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
34~ Do you like the lights on or off during sex?
18- How often do you drink alcohol? What is your favorite drink?
9~ How many times over your lifetime do you think you have had sex so far?
15- What bad habit do you wish you could quit? Do you have any addictions?
28~ What are some things that turn on? What is your biggest turn on?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
3- Should Pluto still be considered a planet? 4- How about smoking?
23- What is your dream job? What was it as a child?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
8- What are your thoughts on politics?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
44~ Care to share something about yourself that no one else knows about you?
27- What was/ is nickname? Does it have a meaning behind it?
11- What's your favorite restaurant? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
3- What’s your favorite smell? Do you a least favorite?
10~ How many dates are necessary before you to have sex with someone?
4- For a pet, Cat, dog or other?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
3- What Superhero or Superpower would you want to be/have?
18~ Who/when was your first “crush”?
65~ Describe the best orgasm you’ve ever had? Care to share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Do you watch it? What is your favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
If yes, what?