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