What is the most interesting question you can ask to get to know someone?
Last Updated: 24.06.2025 07:55
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What are the best (AI) chatbots available online?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Would you do it again, and would you rather 2 females or 2 males?
Master/Slave Boss/Maid
Does the thought excite you? 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…
25~ How do you feel about PDA? (Public Display of Affection)
What is your favorite toy? Ever wanted to try a specific toy?
92~ Everyone needs a “safe” word. What is yours?
Get this wrong and this could mean the end… :-) some funny, some not…
How do schizophrenia symptoms change throughout the day?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
If yes, what?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Secret Characters in Elden Ring Nightreign: How to Unlock the Revenant and Duchess - CNET
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
*** Random Questions ***
13~ Is there a difference between, making love, having sex, and fucking?
When was the first time your wife had beastiality?
51~ What tends to bring a smile to your face?
22- Do you have any birth marks? How about scars? Care to share how you got them?
82~ Do you have any fantasies involving Role-Playing?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
76~ Have you had a threesome? Care to Share?
Do you watch it? What is your favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Escort/Client Job Applicant/Hiring Manager
7- What are your thoughts on religion? Is there an afterlife?
33- If you could visit any time period, when would you pick? Please explain why?
28~ What are some things that turn on? What is your biggest turn on?
11~ Have you ever been caught by your parents or children or others while having sex?
What is the Replika app, and how does it work?
Nurse/Patient Celebrity/Fan
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
13- What is the craziest/scariest thing you've ever done?
Why do men find women with bigger buttocks attractive?
23- What is your dream job? What was it as a child?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
The Ice Breaker Questions
What type of sex do women prefer, oral, anal, or vaginal?
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)
You know that I will be 100% truthful, so ask.
18- What’s your favorite way to relax after a long day? What’s your least favorite?
29- How superstitious are you?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
30~ What's something unexpected that turns you on?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
52~ What are your hobbies?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
If you say it, I will stop, and we can talk about it when you are ready.
45~ How do you feel about me blindfolding you? How about blindfolding me?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
12- What is the weirdest thing you've ever eaten?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Would you read them together?
44~ Care to share something about yourself that no one else knows about you?
15~ Have you ever been “in love”? Who? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
7-What do I do in bed that drives you wild? How about, what turns you off?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
17- What’s your favorite holiday? What’s your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
34- Ever been to a concert? What was your favorite? Who would you like to see?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What is your view on sex? Meaning, When/Where/ How often/
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
51~ Are you willing to play adult games with your partner?
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?
What would you say to prove to yourself that it was really you?
15- What's your favorite saying? What word or phrase is your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
83~ How do you feel about Porn?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
61~ How willing would you be to try new sexual positions?
29~ What are some things that turn you off? What is your biggest turn off?
1- What’s your favorite animal? Do you a least favorite?
Do you think this brought you closer together?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Over time has your thoughts on sex changed?
* Give a rating for each one (0-100)
32- What's your greatest talent? Can I see it right now?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If you win, what will you make them do?
Please share Did you stop?
9- What’s your favorite season and why? What’s your least favorite?
28- What are some things that people do that irritate you?
How old are you? Male or Female?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
19- Do/have you smoked? What do you prefer? How often?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Teacher/Student Stranger/One Night Stand
How well do you know me? And some of your thoughts about me
60~ How important is oral sex? Do you like receiving? Do you like giving?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
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,
18- How often do you drink alcohol? What is your favorite drink?
14- What's your favorite dessert? Do you a least favorite?
17- Have you ever done drugs? Which ones? How often?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
How about if they talk dirty and/or call you names?
21~ What was the best date you ever went on? What has been the worst?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
How many times do you think you have “made love”?
Have you ever? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
3- What Superhero or Superpower would you want to be/have?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
13- How about having a certain hair cut/style?
Nothing too Serious
What is your favorite position? Why?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
9~ How many times over your lifetime do you think you have had sex so far?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
21- What's your favorite way to spend a weekend or time off?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
20- What’s your favorite candy? What’s your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
Will you cheat again? How can, you be sure? Define what cheating is to you.
*** Questions About Me ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
37- Do you like your name? If you could change it, what would you change it too?
36- Do you play video games? What is your favorite? Do you a least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
How many partners have you had oral sex with? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
8- What are your thoughts on politics?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
42~ What’s your biggest regret in life?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
6- Do you have dreams? Can you remember them? What do you usually dream about?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Do you shave/trim your pubic hair? For you guys do you shave your balls?
11- What's your favorite restaurant? What’s your least favorite?
49~ How many times have you been married? Why did they end?
8- What's your favorite flavor of ice cream? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
What have you learned about yourself that you did not before this?
53~ How much can you tell me about the one thing you are most passionate about?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
10- List 5 of your top pet peeves.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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?
62~ Have you used adult toys?
*** Questions about Relationships/Past ***
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
5- Have you ever been hypnotized? Would you allow yourself to be?
If NO, would you ever have one? Would it be with 2 men or 2 women?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Any that are a turn off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
81~ Do you have any kinks and/or fetishes?
Do you have a favorite? Is it ok if your partner does?
19~ Who/when was your first “heartbreak”?
9- Is there something you’ve always wanted to ask me but you’re afraid?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
36~ What is your favorite time of day to have sex/make love?
Would you mind if your partner watched it? How about together vs alone?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
48~ Do you have any siblings? Are you close to your family?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
50~ How many children do you have? What are their ages?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
I would allow you to do it… What would you do to me?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
4- For a pet, Cat, dog or other?
89~ Do you like taking showers together?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
18~ Who/when was your first “crush”?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
3- Should Pluto still be considered a planet? 4- How about smoking?
11- How about if they like a certain sports team? 12-How about drinking too much?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
71~ Would you give your partner a hand or foot job? Would you receive one?
What do you dislike about me? I asked you to be 100% honest.
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
9- If you could have three wishes, what would they be? Why?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would you ever want to be woken up with oral and/or intercourse?
52~ Are you willing to make “those types” of bets with your partner?
12- What’s your favorite food? What’s your least favorite?
70~ Would/do you have/like anal sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
(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…)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
15- What bad habit do you wish you could quit? Do you have any addictions?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
13- What’s your favorite drink? What’s your least favorite?
2- What’s your favorite color? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
10~ How many dates are necessary before you to have sex with someone?
What have you learned about me that was new and/or surprising?
3- What’s your favorite smell? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
26~ What side of the bed do you sleep on?
84~ How do you feel about reading/listening to adult stories?
33- Beach or Mountains? Or is there another place to like better?
If YES, was it with 2 men or 2 women? Did you enjoy it?
47~ What would be your dream job and why?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
1~ How old were you when you had your first kiss? Who? Care to Share?
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?
1- What was your first impression of me? Has it changed?
65~ Describe the best orgasm you’ve ever had? Care to share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Prisoner/Prison Guard Landlord/Tenant
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Any that are a turn off?
38~ Share your most embarrassing sexual memory?
5~ When you first started having sex, was it what you thought it would be?
92~ Have you ever had or have an STD? How many? What was it?
*** Deal Breaker Questions ***
39~ What are your love languages?
67~ Do you like it when your partner moans and/or is vocal during sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
What was the longest? What was the shortest?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
34~ Do you like the lights on or off during sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
Family Relation Age Play
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Doctor/Nurse Stripper/Client
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
40~ What’s the weirdest place you’ve ever had sex?
19- What’s your favorite fairytale? What’s your least favorite?
Model/Photographer Police/Criminal
*** What’s Your 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…
27- What was/ is nickname? Does it have a meaning behind it?
Repairman/Lonely Wife Virgin/Experienced
31- If given a chance to be immortal, would you take it? Why?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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?
Would /have you ever given your partner a lap dance and Striptease?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?