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