What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 12:53
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Repairman/Lonely Wife Virgin/Experienced
Doctor/Nurse Stripper/Client
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
That one or two things that made you go hmmmm, OMG or wow!
52~ What are your hobbies?
Why am I so jealous towards couples? Why am I tired of being single and feel my life is over?
How about if they talk dirty and/or call you names?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
*** Questions About Me ***
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39~ What are your love languages?
89~ Do you like taking showers together?
If you win, what will you make them do?
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42~ What’s your biggest regret in life?
7- What if a person smells a certain way? 8- How about smoking?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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18- What’s your favorite way to relax after a long day? What’s your least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Fugiat rerum itaque dolorem rem.
If yes, what?
How old are you? Male or Female?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
15- What bad habit do you wish you could quit? Do you have any addictions?
76~ Have you had a threesome? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Has anyone ever worn leather pants? Are they comfortable?
11- How about if they like a certain sports team? 12-How about drinking too much?
Do you have a favorite? Is it ok if your partner does?
82~ Do you have any fantasies involving Role-Playing?
27- What was/ is nickname? Does it have a meaning behind it?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Over time has your thoughts on sex changed?
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If NO, would you ever have one? Would it be with 2 men or 2 women?
18- How often do you drink alcohol? What is your favorite drink?
Nurse/Patient Celebrity/Fan
Master/Slave Boss/Maid
What’s the longest time you gone without having sex, after, having it? How much time between the others?
5- Have you ever been hypnotized? Would you allow yourself to be?
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6- What’s your favorite TV series? Do you have a favorite genre? Do you a 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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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9- What’s your favorite season and why? What’s your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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3- What Superhero or Superpower would you want to be/have?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
44~ Care to share something about yourself that no one else knows about you?
19- Do/have you smoked? What do you prefer? How often?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
8- What are your thoughts on politics?
17- Have you ever done drugs? Which ones? How often?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What was the longest? What was the shortest?
52~ Are you willing to make “those types” of bets with your partner?
50~ How many children do you have? What are their ages?
40~ What’s the weirdest place you’ve ever had sex?
*** Deal Breaker Questions ***
29~ What are some things that turn you off? What is your biggest turn off?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
11~ Have you ever been caught by your parents or children or others while having sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
30~ What's something unexpected that turns you on?
53~ How much can you tell me about the one thing you are most passionate about?
12- What is the weirdest thing you've ever eaten?
34- Ever been to a concert? What was your favorite? Who would you like to see?
10~ How many dates are necessary before you to have sex with someone?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
47~ What would be your dream job and why?
19~ Who/when was your first “heartbreak”?
Would you read them together?
Do you think this brought you closer together?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
How many partners have you had oral sex with? Who? Care to Share?
62~ Have you used adult toys?
19- What’s your favorite fairytale? What’s your least favorite?
Do you watch it? What is your favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
Do you like it when they show and tell you what they want?
65~ Describe the best orgasm you’ve ever had? Care to share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Have you ever? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
12- What’s your favorite food? What’s your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What have you learned about me that was new and/or surprising?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
26~ What side of the bed do you sleep on?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How many times do you think you have “made love”?
92~ Everyone needs a “safe” word. What is yours?
28- What are some things that people do that irritate you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
8- What's your favorite flavor of ice cream? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
28~ What are some things that turn on? What is your biggest turn on?
48~ Have you ever paid or been paid for sex?
51~ What tends to bring a smile to your face?
What is your view on sex? Meaning, When/Where/ How often/
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Escort/Client Job Applicant/Hiring Manager
Any that are a turn off?
81~ Do you have any kinks and/or fetishes?
1~ How old were you when you had your first kiss? Who? Care to Share?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Any that are a turn off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Get this wrong and this could mean the end… :-) some funny, some not…
* Give a rating for each one (0-100)
11- What's your favorite restaurant? What’s your least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
21- What's your favorite way to spend a weekend or time off?
Will you cheat again? How can, you be sure? Define what cheating is to you.
What do you dislike about me? I asked you to be 100% honest.
21~ What was the best date you ever went on? What has been the worst?
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,
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…
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Would you do it again, and would you rather 2 females or 2 males?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
4- For a pet, Cat, dog or other?
33- Beach or Mountains? Or is there another place to like better?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How well do you know me? And some of your thoughts about me
23- What is your dream job? What was it as a child?
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?
37- Do you like your name? If you could change it, what would you change it too?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
*** Questions about Relationships/Past ***
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What would you say to prove to yourself that it was really you?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Does the thought excite you? Care to share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
34~ Do you like the lights on or off during 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…
6- Do you have dreams? Can you remember them? What do you usually dream about?
61~ How willing would you be to try new sexual positions?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
3- Should Pluto still be considered a planet? 4- How about smoking?
13- What is the craziest/scariest thing you've ever done?
17- What’s your favorite holiday? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
67~ Do you like it when your partner moans and/or is vocal during sex?
10- What is your favorite family tradition? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
15~ Have you ever been “in love”? Who? Care to Share?
What is your favorite position? Why?
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?
92~ Have you ever had or have an STD? How many? What was it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Would you ever want to be woken up with oral and/or intercourse?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
36- Do you play video games? What is your favorite? Do you a least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
9~ How many times over your lifetime do you think you have had sex so far?
25~ How do you feel about PDA? (Public Display of Affection)
32- What's your greatest talent? Can I see it right now?
70~ Would/do you have/like anal sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
7- What are your thoughts on religion? Is there an afterlife?
Family Relation Age Play
22- What is your favorite childhood memory? What is your least favorite?
9- If you could have three wishes, what would they be? Why?
10- List 5 of your top pet peeves.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Model/Photographer Police/Criminal
48~ Do you have any siblings? Are you close to your family?
18~ Who/when was your first “crush”?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
51~ Are you willing to play adult games with your partner?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
20- What’s your favorite candy? What’s your least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
15- What's your favorite saying? What word or phrase is your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
13- How about having a certain hair cut/style?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
49~ How many times have you been married? Why did they end?
Nothing too Serious
What is your favorite toy? Ever wanted to try a specific toy?
You know that I will be 100% truthful, so ask.
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
(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…)
13- What’s your favorite drink? What’s your least favorite?
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Please share Did you stop?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Teacher/Student Stranger/One Night Stand
Can you Deep Throat? Do you like the taste of yourself?
1- What was your first impression of me? Has it changed?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
I would allow you to do it… What would you do to me?
38~ Share your most embarrassing sexual memory?
1- What’s your favorite animal? Do you a least favorite?
31- If given a chance to be immortal, would you take it? Why?
11- List at least 5 things on your bucket list. Have you done any of them already?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
84~ How do you feel about reading/listening to adult stories?
What have you learned about yourself that you did not before this?
*** Random Questions ***
83~ How do you feel about Porn?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
3- What’s your favorite smell? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
The Ice Breaker Questions
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Do you like the “69” position? Do you prefer to be on top or bottom?
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)
Would you allow me to clean every part of your body with my soapy hands and fingers?
13~ Is there a difference between, making love, having sex, and fucking?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
36~ What is your favorite time of day to have sex/make love?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
2- What’s your favorite color? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
71~ Would you give your partner a hand or foot job? Would you receive one?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
33- If you could visit any time period, when would you pick? Please explain why?
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?
29- How superstitious are you?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Would you mind if your partner watched it? How about together vs alone?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Would /have you ever given your partner a lap dance and Striptease?
*** What’s Your Favorite…? ***