What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 01:30
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
21~ What was the best date you ever went on? What has been the worst?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
What are some funny and smart quotes?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
25~ How do you feel about PDA? (Public Display of Affection)
47~ What would be your dream job and why?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How can I stop overthinking and take action more quickly?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How old are you? Male or Female?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Have you ever forcibly sucked someone’s dick?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
When do you start "growing old"?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
13- What’s your favorite drink? What’s your least favorite?
Does the thought excite you? Care to share?
My boyfriend won’t tell me his past and it hurts me so I broke up with him what do I do?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
5- Have you ever been hypnotized? Would you allow yourself to be?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What have you learned about yourself that you did not before this?
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)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Is the Las Vegas Grand Prix considered one of the "premier events on the Formula 1 calendar?"
28- What are some things that people do that irritate you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Family Relation Age Play
What is the best way to get over your ex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
Why are American women so ugly nowadays?
3- What Superhero or Superpower would you want to be/have?
Doctor/Nurse Stripper/Client
2- What’s your favorite color? Do you a least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How can people balance religious beliefs with seeking professional mental health care?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
83~ How do you feel about Porn?
Nothing too Serious
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
71~ Would you give your partner a hand or foot job? Would you receive one?
Why is Tiananmen Square censored?
53~ How much can you tell me about the one thing you are most passionate about?
Please share Did you stop?
22- Do you have any birth marks? How about scars? Care to share how you got them?
34- Ever been to a concert? What was your favorite? Who would you like to see?
How about if they talk dirty and/or call you names?
14- What's your favorite dessert? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What do you dislike about me? I asked you to be 100% honest.
51~ What tends to bring a smile to your face?
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?
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- List at least 5 things on your bucket list. Have you done any of them already?
Do you like it when they show and tell you what they want?
80~ Share your top three fantasies/desires. (Be detailed) 😊
22- What is your favorite childhood memory? What is your least favorite?
*** Questions About Me ***
1~ How old were you when you had your first kiss? Who? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
33- If you could visit any time period, when would you pick? Please explain why?
Nurse/Patient Celebrity/Fan
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Over time has your thoughts on sex changed?
What is your favorite toy? Ever wanted to try a specific toy?
30~ What's something unexpected that turns you on?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
7-What do I do in bed that drives you wild? How about, what turns you off?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you ever want to be woken up with oral and/or intercourse?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** Deal Breaker Questions ***
15- What bad habit do you wish you could quit? Do you have any addictions?
37- Do you like your name? If you could change it, what would you change it too?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
52~ Are you willing to make “those types” of bets with your partner?
Do you watch it? What is your favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
You know that I will be 100% truthful, so ask.
Would /have you ever given your partner a lap dance and Striptease?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
50~ How many children do you have? What are their ages?
(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…)
15- What's your favorite saying? What word or phrase is your least favorite?
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?
I would allow you to do it… What would you do to me?
76~ Have you had a threesome? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
28~ What are some things that turn on? What is your biggest turn on?
5~ When you first started having sex, was it what you thought it would be?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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,
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Master/Slave Boss/Maid
82~ Do you have any fantasies involving Role-Playing?
1- What’s your favorite animal? Do you a least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
21- What's your favorite way to spend a weekend or time off?
52~ What are your hobbies?
If YES, was it with 2 men or 2 women? Did you enjoy it?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Any that are a turn off?
9~ How many times over your lifetime do you think you have had sex so far?
How well do you know me? And some of your thoughts about me
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
29~ What are some things that turn you off? What is your biggest turn off?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
27- What was/ is nickname? Does it have a meaning behind it?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
10- List 5 of your top pet peeves.
34~ Do you like the lights on or off during sex?
36- Do you play video games? What is your favorite? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
18~ Who/when was your first “crush”?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Have you ever? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
12- What’s your favorite food? What’s your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Repairman/Lonely Wife Virgin/Experienced
48~ Do you have any siblings? Are you close to your family?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
81~ Do you have any kinks and/or fetishes?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
92~ Everyone needs a “safe” word. What is yours?
29- How superstitious are you?
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?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
48~ Have you ever paid or been paid for sex?
13- How about having a certain hair cut/style?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Any that are a turn off?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
10~ How many dates are necessary before you to have sex with someone?
31- If given a chance to be immortal, would you take it? Why?
32- What's your greatest talent? Can I see it right now?
33- Beach or Mountains? Or is there another place to like better?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Model/Photographer Police/Criminal
9- What’s your favorite season and why? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
What would you say to prove to yourself that it was really you?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
62~ Have you used adult toys?
Do you have a favorite? Is it ok if your partner does?
Prisoner/Prison Guard Landlord/Tenant
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
17- Have you ever done drugs? Which ones? How often?
Teacher/Student Stranger/One Night Stand
11~ Have you ever been caught by your parents or children or others while having sex?
4- For a pet, Cat, dog or other?
If you win, what will you make them do?
The Ice Breaker Questions
3- What was the most surprising thing you’ve learned about me throughout our relationship?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
36~ What is your favorite time of day to have sex/make love?
*** Questions about Relationships/Past ***
If you say it, I will stop, and we can talk about it when you are ready.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Escort/Client Job Applicant/Hiring Manager
Get this wrong and this could mean the end… :-) some funny, some not…
That one or two things that made you go hmmmm, OMG or wow!
11- How about if they like a certain sports team? 12-How about drinking too much?
How many times do you think you have “made love”?
If NO, would you ever have one? Would it be with 2 men or 2 women?
38~ Share your most embarrassing sexual memory?
*** What’s Your Favorite…? ***
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
Would you read them together?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
19~ Who/when was your first “heartbreak”?
20- What’s your favorite candy? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
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…
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
26~ What side of the bed do you sleep on?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
10- What is your favorite family tradition? What’s your least favorite?
Do you think this brought you closer together?
9- If you could have three wishes, what would they be? Why?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
Can you Deep Throat? Do you like the taste of yourself?
8- What are your thoughts on politics?
What is your favorite position? Why?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
61~ How willing would you be to try new sexual positions?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
1- What was your first impression of me? Has it changed?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Will you cheat again? How can, you be sure? Define what cheating is to you.
19- What’s your favorite fairytale? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What was the longest? What was the shortest?
51~ Are you willing to play adult games with your partner?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
* Give a rating for each one (0-100)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What have you learned about me that was new and/or surprising?
3- What’s your favorite smell? Do you a least favorite?
92~ Have you ever had or have an STD? How many? What was it?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Would you mind if your partner watched it? How about together vs alone?
70~ Would/do you have/like anal sex?
17- What’s your favorite holiday? What’s your least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
13- What is the craziest/scariest thing you've ever done?
*** Random Questions ***
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
89~ Do you like taking showers together?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7- What if a person smells a certain way? 8- How about smoking?
23- What is your dream job? What was it as a child?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
44~ Care to share something about yourself that no one else knows about you?
13~ Is there a difference between, making love, having sex, and fucking?
18- How often do you drink alcohol? What is your favorite drink?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
39~ What are your love languages?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
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?
How many partners have you had oral sex with? Who? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
12- What is the weirdest thing you've ever eaten?
Would you do it again, and would you rather 2 females or 2 males?
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…
11- What's your favorite restaurant? What’s your least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If yes, what?
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?
7- What are your thoughts on religion? Is there an afterlife?