What is the most interesting question you can ask to get to know someone?
Last Updated: 25.06.2025 01:59
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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…
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Would you ever want to be woken up with oral and/or intercourse?
42~ What’s your biggest regret in life?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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8- What are your thoughts on politics?
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?
22- What is your favorite childhood memory? What is your least favorite?
48~ Do you have any siblings? Are you close to your family?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
12 Tips For The Alters You Need To Know Before You Play - GameSpot
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Would you do it again, and would you rather 2 females or 2 males?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
36~ What is your favorite time of day to have sex/make love?
15- What's your favorite saying? What word or phrase is your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Nice Hat, Loser - aftermath.site
Please share Did you stop?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
What is something you want to "get off your chest"?
Nothing too Serious
Would you read them together?
15~ Have you ever been “in love”? Who? Care to Share?
What are the best self-care practices to improve mental health?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
23- What is your dream job? What was it as a child?
92~ Everyone needs a “safe” word. What is yours?
What was the longest? What was the shortest?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
22- Do you have any birth marks? How about scars? Care to share how you got them?
How about if they talk dirty and/or call you names?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
How well do you know me? And some of your thoughts about me
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11- What's your favorite restaurant? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Do you think this brought you closer together?
81~ Do you have any kinks and/or fetishes?
Get this wrong and this could mean the end… :-) some funny, some not…
84~ How do you feel about reading/listening to adult stories?
Teacher/Student Stranger/One Night Stand
Have you ever? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
*** Questions about Relationships/Past ***
24~ What are your expectations in a relationship? (I know a very big question, take your time)
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
25~ How do you feel about PDA? (Public Display of Affection)
17- What’s your favorite holiday? What’s your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
2- What’s your favorite color? Do you a least favorite?
(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…)
39~ What are your love languages?
13- What is the craziest/scariest thing you've ever done?
33- Beach or Mountains? Or is there another place to like better?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
11- List at least 5 things on your bucket list. Have you done any of them already?
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,
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What is your view on sex? Meaning, When/Where/ How often/
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
7- What are your thoughts on religion? Is there an afterlife?
13- What’s your favorite drink? What’s your least favorite?
Any that are a turn off?
34~ Do you like the lights on or off during sex?
Would you mind if your partner watched it? How about together vs alone?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
48~ Have you ever paid or been paid for sex?
13- How about having a certain hair cut/style?
29- How superstitious are you?
44~ Care to share something about yourself that no one else knows about you?
Prisoner/Prison Guard Landlord/Tenant
How many partners have you had oral sex with? Who? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
47~ What would be your dream job and why?
If you win, what will you make them do?
12- What is the weirdest thing you've ever eaten?
70~ Would/do you have/like anal sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
If yes, what?
18- How often do you drink alcohol? What is your favorite drink?
* Give a rating for each one (0-100)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
8- What's your favorite flavor of ice cream? Do you a least favorite?
28- What are some things that people do that irritate you?
78~ Have you ever thought about making out or having sex with someone of the same sex? 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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
*** What’s Your Favorite…? ***
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Family Relation Age Play
You know that I will be 100% truthful, so ask.
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Would /have you ever given your partner a lap dance and Striptease?
Master/Slave Boss/Maid
Nurse/Patient Celebrity/Fan
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Do you have a favorite? Is it ok if your partner does?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
Do you watch it? What is your favorite?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
5~ When you first started having sex, was it what you thought it would be?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
32- What's your greatest talent? Can I see it right now?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
Can you Deep Throat? Do you like the taste of yourself?
Model/Photographer Police/Criminal
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
1- What’s your favorite animal? Do you a least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
If you say it, I will stop, and we can talk about it when you are ready.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
9- What’s your favorite season and why? What’s your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
67~ Do you like it when your partner moans and/or is vocal during sex?
*** Deal Breaker Questions ***
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What is your favorite toy? Ever wanted to try a specific toy?
51~ Are you willing to play adult games with your partner?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
45~ How do you feel about me blindfolding you? How about blindfolding me?
38~ Share your most embarrassing sexual memory?
11~ Have you ever been caught by your parents or children or others while having sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
26~ What side of the bed do you sleep on?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
10~ How many dates are necessary before you to have sex with someone?
Any that are a turn off?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
12- What’s your favorite food? What’s your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
60~ How important is oral sex? Do you like receiving? Do you like giving?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
89~ Do you like taking showers together?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
14- What is an embarrassing moment in your life? How about your most embarrassing?
3- Should Pluto still be considered a planet? 4- How about smoking?
83~ How do you feel about Porn?
14- What's your favorite dessert? Do you a least favorite?
How old are you? Male or Female?
9- Is there something you’ve always wanted to ask me but you’re afraid?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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…
11- How about if they like a certain sports team? 12-How about drinking too much?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
31- If given a chance to be immortal, would you take it? Why?
10- List 5 of your top pet peeves.
Doctor/Nurse Stripper/Client
65~ Describe the best orgasm you’ve ever had? Care to share?
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)
13~ Is there a difference between, making love, having sex, and fucking?
37- Do you like your name? If you could change it, what would you change it too?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
50~ How many children do you have? What are their ages?
6- Do you have dreams? Can you remember them? What do you usually dream about?
7- What if a person smells a certain way? 8- How about smoking?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
I would allow you to do it… What would you do to me?
19- What’s your favorite fairytale? What’s your least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
34- Ever been to a concert? What was your favorite? Who would you like to see?
5- Have you ever been hypnotized? Would you allow yourself to be?
17- Have you ever done drugs? Which ones? How often?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If NO, would you ever have one? Would it be with 2 men or 2 women?
Does the thought excite you? Care to share?
40~ What’s the weirdest place you’ve ever had sex?
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?
Repairman/Lonely Wife Virgin/Experienced
21- What's your favorite way to spend a weekend or time off?
*** Random Questions ***
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
49~ How many times have you been married? Why did they end?
Do you like it when they show and tell you what they want?
4- For a pet, Cat, dog or other?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
21~ What was the best date you ever went on? What has been the worst?
Do you like the “69” position? Do you prefer to be on top or bottom?
Escort/Client Job Applicant/Hiring Manager
1- What was your first impression of me? Has it changed?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
3- What’s your favorite smell? Do you a least favorite?
19~ Who/when was your first “heartbreak”?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How many times do you think you have “made love”?
30~ What's something unexpected that turns you on?
71~ Would you give your partner a hand or foot job? Would you receive one?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
The Ice Breaker Questions
28~ What are some things that turn on? What is your biggest turn on?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
18~ Who/when was your first “crush”?
10- What is your favorite family tradition? What’s your least favorite?
52~ What are your hobbies?
1~ How old were you when you had your first kiss? Who? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
61~ How willing would you be to try new sexual positions?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What have you learned about yourself that you did not before this?
*** Questions About Me ***
9- If you could have three wishes, what would they be? Why?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
27- What was/ is nickname? Does it have a meaning behind it?
53~ How much can you tell me about the one thing you are most passionate about?
62~ Have you used adult toys?
80~ Share your top three fantasies/desires. (Be detailed) 😊
9~ How many times over your lifetime do you think you have had sex so far?
76~ Have you had a threesome? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
29~ What are some things that turn you off? What is your biggest turn off?
52~ Are you willing to make “those types” of bets with your partner?
What is your favorite position? Why?
33- If you could visit any time period, when would you pick? Please explain why?
82~ Do you have any fantasies involving Role-Playing?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What have you learned about me that was new and/or surprising?
Over time has your thoughts on sex changed?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
That one or two things that made you go hmmmm, OMG or wow!
What would you say to prove to yourself that it was really you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
51~ What tends to bring a smile to your face?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?