What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 23:44
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
40~ What’s the weirdest place you’ve ever had sex?
*** Questions about Relationships/Past ***
Which scene is considered the most difficult to watch in each of Quentin Tarantino's movies?
11- What's your favorite restaurant? What’s your least favorite?
47~ What would be your dream job and why?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Who is the most trusted person in your life, and do they have the same trust on you?
*** Random Questions ***
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
49~ How many times have you been married? Why did they end?
Why am I so tired of the keto diet?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
28- What are some things that people do that irritate 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…
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
30~ What's something unexpected that turns you on?
48~ Have you ever paid or been paid for sex?
62~ Have you used adult toys?
82~ Do you have any fantasies involving Role-Playing?
92~ Everyone needs a “safe” word. What is yours?
44~ Care to share something about yourself that no one else knows about you?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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,
Would /have you ever given your partner a lap dance and Striptease?
Why do people stay in cults after they have joined?
17- What’s your favorite holiday? What’s your least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
Get this wrong and this could mean the end… :-) some funny, some not…
4 ways the Desmond Bane trade could affect the Celtics - Boston.com
Family Relation Age Play
24~ What are your expectations in a relationship? (I know a very big question, take your time)
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What have you learned about me that was new and/or surprising?
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)
How about if they talk dirty and/or call you names?
Is depression a cause for always feeling tired?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
14- What's your favorite dessert? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
10~ How many dates are necessary before you to have sex with someone?
84~ How do you feel about reading/listening to adult stories?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What is your most erotic sex story?
What have you learned about yourself that you did not before this?
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?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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?
31- If given a chance to be immortal, would you take it? Why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
27- What was/ is nickname? Does it have a meaning behind it?
*** What’s Your Favorite…? ***
1- What’s your favorite animal? Do you a least favorite?
10- List 5 of your top pet peeves.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Nothing too Serious
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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Would you read them together?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Do you watch it? What is your favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you think this brought you closer together?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
76~ Have you had a threesome? Care to Share?
61~ How willing would you be to try new sexual positions?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If you win, what will you make them do?
Do you like it when they show and tell you what they want?
42~ What’s your biggest regret in life?
You know that I will be 100% truthful, so ask.
33- Beach or Mountains? Or is there another place to like better?
If yes, what?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
48~ Do you have any siblings? Are you close to your family?
32- What's your greatest talent? Can I see it right now?
22- What is your favorite childhood memory? What is your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
11- How about if they like a certain sports team? 12-How about drinking too much?
* 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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
92~ Have you ever had or have an STD? How many? What was it?
If NO, would you ever have one? Would it be with 2 men or 2 women?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
36~ What is your favorite time of day to have sex/make love?
Over time has your thoughts on sex changed?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
70~ Would/do you have/like anal sex?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Prisoner/Prison Guard Landlord/Tenant
60~ How important is oral sex? Do you like receiving? Do you like giving?
23- What is your dream job? What was it as a child?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
21- What's your favorite way to spend a weekend or time off?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Doctor/Nurse Stripper/Client
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you allow me to clean every part of your body with my soapy hands and fingers?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
29- How superstitious are you?
2- What’s your favorite color? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
(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…)
Teacher/Student Stranger/One Night Stand
The Ice Breaker Questions
*** Questions About Me ***
Do you shave/trim your pubic hair? For you guys do you shave your balls?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
50~ How many children do you have? What are their ages?
52~ Are you willing to make “those types” of bets with your partner?
Please share Did you stop?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Can you Deep Throat? Do you like the taste of yourself?
19- What’s your favorite fairytale? What’s your least favorite?
12- What’s your favorite food? What’s your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
38~ Share your most embarrassing sexual memory?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
90~ Have you ever had sex in a Pool or Hot Tub? Would 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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
If YES, was it with 2 men or 2 women? Did you enjoy it?
How old are you? Male or Female?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
29~ What are some things that turn you off? What is your biggest turn off?
3- What’s your favorite smell? Do you a least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
83~ How do you feel about Porn?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
9- If you could have three wishes, what would they be? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
8- What's your favorite flavor of ice cream? 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?
How many times do you think you have “made love”?
33- If you could visit any time period, when would you pick? Please explain why?
Master/Slave Boss/Maid
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
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?
19- Do/have you smoked? What do you prefer? How often?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
13- How about having a certain hair cut/style?
1~ How old were you when you had your first kiss? Who? Care to Share?
How well do you know me? And some of your thoughts about me
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
17- Have you ever done drugs? Which ones? How often?
20- What’s your favorite candy? What’s your least favorite?
What was the longest? What was the shortest?
I would allow you to do it… What would you do to me?
10- What is your favorite family tradition? What’s your least favorite?
Any that are a turn off?
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?
71~ Would you give your partner a hand or foot job? Would you receive one?
39~ What are your love languages?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
25~ How do you feel about PDA? (Public Display of Affection)
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Have you ever? Care to Share?
1- What was your first impression of me? Has it changed?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
18- How often do you drink alcohol? What is your favorite drink?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Model/Photographer Police/Criminal
12- What is the weirdest thing you've ever eaten?
51~ Are you willing to play adult games with your partner?
What would you say to prove to yourself that it was really you?
Repairman/Lonely Wife Virgin/Experienced
15~ Have you ever been “in love”? Who? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
89~ Do you like taking showers together?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
51~ What tends to bring a smile to your face?
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?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Nurse/Patient Celebrity/Fan
Do you like the “69” position? Do you prefer to be on top or bottom?
26~ What side of the bed do you sleep on?
7- What if a person smells a certain way? 8- How about smoking?
Does the thought excite you? Care to share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
45~ How do you feel about me blindfolding you? How about blindfolding me?
How many partners have you had oral sex with? Who? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would you do it again, and would you rather 2 females or 2 males?
3- Should Pluto still be considered a planet? 4- How about smoking?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
What is your view on sex? Meaning, When/Where/ How often/
15- What bad habit do you wish you could quit? Do you have any addictions?
19~ Who/when was your first “heartbreak”?
That one or two things that made you go hmmmm, OMG or wow!
3- What Superhero or Superpower would you want to be/have?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
13~ Is there a difference between, making love, having sex, and fucking?
9- What’s your favorite season and why? What’s your least favorite?
37- Do you like your name? If you could change it, what would you change it too?
Any that are a turn off?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you have a favorite? Is it ok if your partner does?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
*** Deal Breaker Questions ***
What is your favorite toy? Ever wanted to try a specific toy?
18~ Who/when was your first “crush”?
34~ Do you like the lights on or off during sex?
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 is your favorite position? Why?
65~ Describe the best orgasm you’ve ever had? Care to share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
9~ How many times over your lifetime do you think you have had sex so far?
13- What is the craziest/scariest thing you've ever done?
Would you mind if your partner watched it? How about together vs alone?
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Escort/Client Job Applicant/Hiring Manager
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Would you ever want to be woken up with oral and/or intercourse?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
13- What’s your favorite drink? What’s your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
21~ What was the best date you ever went on? What has been the worst?
5~ When you first started having sex, was it what you thought it would be?
81~ Do you have any kinks and/or fetishes?
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…
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
7- What are your thoughts on religion? Is there an afterlife?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
36- Do you play video games? What is your favorite? Do you a least favorite?
What do you dislike about me? I asked you to be 100% honest.
52~ What are your hobbies?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
8- What are your thoughts on politics?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
4- For a pet, Cat, dog or other?
14- What is an embarrassing moment in your life? How about your most embarrassing?
5- Have you ever been hypnotized? Would you allow yourself to be?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?