What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 02:42
Do you like it when they show and tell you what they want?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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?
70~ Would/do you have/like anal sex?
3- What’s your favorite smell? Do you a least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
Why doesn’t Melania Trump do some more modeling?
8- What are your thoughts on politics?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
19- Do/have you smoked? What do you prefer? How often?
What is the difference between heaven and heavens?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
82~ Do you have any fantasies involving Role-Playing?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Hackers take aim at Washington Post journalists in an apparent ‘targeted’ cyberattack - CNN
11- What's your favorite restaurant? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
(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…)
Newspaper headlines: 'A generation let down' and 'Israel claims control' - BBC
Get this wrong and this could mean the end… :-) some funny, some not…
You know that I will be 100% truthful, so ask.
33- Beach or Mountains? Or is there another place to like better?
Rabid fox bites person in Raleigh - WRAL.com
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Model/Photographer Police/Criminal
7-What do I do in bed that drives you wild? How about, what turns you off?
Does any other guys get turned on by dick pic makes you lick lips because you what to suck?
The Ice Breaker Questions
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Why do people have polyamorous relationships?
39~ What are your love languages?
92~ Have you ever had or have an STD? How many? What was it?
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?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What is your favorite position? Why?
7- What are your thoughts on religion? Is there an afterlife?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** Random Questions ***
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
89~ Do you like taking showers together?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
13- How about having a certain hair cut/style?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
28~ What are some things that turn on? What is your biggest turn on?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
64~ When was your very first orgasm? When was your first from having sex? 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)
Do you watch it? What is your favorite?
What do you dislike about me? I asked you to be 100% honest.
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Over time has your thoughts on sex changed?
9- What’s your favorite season and why? What’s your least favorite?
10- What is your favorite family tradition? What’s your least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If YES, was it with 2 men or 2 women? Did you enjoy it?
11- How about if they like a certain sports team? 12-How about drinking too much?
25~ How do you feel about PDA? (Public Display of Affection)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
That one or two things that made you go hmmmm, OMG or wow!
Does the thought excite you? Care to share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
What is your favorite toy? Ever wanted to try a specific toy?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
28- What are some things that people do that irritate you?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Nurse/Patient Celebrity/Fan
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
13- What’s your favorite drink? What’s your least favorite?
What have you learned about yourself that you did not before this?
Doctor/Nurse Stripper/Client
Do you like the “69” position? Do you prefer to be on top or bottom?
8- What's your favorite flavor of ice cream? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
1~ How old were you when you had your first kiss? Who? Care to Share?
*** Questions About Me ***
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
51~ What tends to bring a smile to your face?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
If you win, what will you make them do?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
19- What’s your favorite fairytale? What’s your least favorite?
29- How superstitious are you?
27- What was/ is nickname? Does it have a meaning behind it?
47~ What would be your dream job and why?
12- What’s your favorite food? What’s your least favorite?
3- What Superhero or Superpower would you want to be/have?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What have you learned about me that was new and/or surprising?
17- What’s your favorite holiday? What’s your least favorite?
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?
* Give a rating for each one (0-100)
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
42~ What’s your biggest regret in life?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
60~ How important is oral sex? Do you like receiving? Do you like giving?
20- What’s your favorite candy? What’s your least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
33- If you could visit any time period, when would you pick? Please explain why?
21- What's your favorite way to spend a weekend or time off?
10- List 5 of your top pet peeves.
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
4- For a pet, Cat, dog or other?
How well do you know me? And some of your thoughts about me
34~ Do you like the lights on or off during sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Would you read them together?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
52~ What are your hobbies?
Can you Deep Throat? Do you like the taste of yourself?
36~ What is your favorite time of day to have sex/make love?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
5- Have you ever been hypnotized? Would you allow yourself to be?
How about if they talk dirty and/or call you names?
92~ Everyone needs a “safe” word. What is yours?
10~ How many dates are necessary before you to have sex with someone?
11- List at least 5 things on your bucket list. Have you done any of them already?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
11~ Have you ever been caught by your parents or children or others while having sex?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
17- Have you ever done drugs? Which ones? How often?
*** Questions about Relationships/Past ***
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** What’s Your Favorite…? ***
Do you think this brought you closer together?
Would you mind if your partner watched it? How about together vs alone?
31- If given a chance to be immortal, would you take it? Why?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
18~ Who/when was your first “crush”?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
81~ Do you have any kinks and/or fetishes?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
1- What was your first impression of me? Has it changed?
If you say it, I will stop, and we can talk about it when you are ready.
49~ If you could, would you want to be the opposite sex for a day, week, or year?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
49~ How many times have you been married? Why did they end?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
44~ Care to share something about yourself that no one else knows about you?
62~ Have you used adult toys?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
29~ What are some things that turn you off? What is your biggest turn off?
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?
If yes, what?
Master/Slave Boss/Maid
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
Would you do it again, and would you rather 2 females or 2 males?
Nothing too Serious
23- What is your dream job? What was it as a child?
Family Relation Age Play
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
What would you say to prove to yourself that it was really you?
18- How often do you drink alcohol? What is your favorite drink?
How many partners have you had oral sex with? Who? Care to Share?
19~ Who/when was your first “heartbreak”?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
84~ How do you feel about reading/listening to adult stories?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
15~ Have you ever been “in love”? Who? Care to Share?
Please share Did you stop?
If NO, would you ever have one? Would it be with 2 men or 2 women?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
I would allow you to do it… What would you do to me?
Would /have you ever given your partner a lap dance and Striptease?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
83~ How do you feel about Porn?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
36- Do you play video games? What is your favorite? Do you a least favorite?
2- What’s your favorite color? Do you a least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
50~ How many children do you have? What are their ages?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Any that are a turn off?
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?
Teacher/Student Stranger/One Night Stand
38~ Share your most embarrassing sexual memory?
7- What if a person smells a certain way? 8- How about smoking?
12- What is the weirdest thing you've ever eaten?
Do you have a favorite? Is it ok if your partner does?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
9~ How many times over your lifetime do you think you have had sex so far?
How old are you? Male or Female?
What was the longest? What was the shortest?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
40~ What’s the weirdest place you’ve ever had sex?
61~ How willing would you be to try new sexual positions?
65~ Describe the best orgasm you’ve ever had? 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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
How many times do you think you have “made love”?
9- If you could have three wishes, what would they be? Why?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
5~ When you first started having sex, was it what you thought it would be?
32- What's your greatest talent? Can I see it right now?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Any that are a turn off?
53~ How much can you tell me about the one thing you are most passionate about?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
22- What is your favorite childhood memory? What is your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
52~ Are you willing to make “those types” of bets with your partner?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
26~ What side of the bed do you sleep on?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
76~ Have you had a threesome? Care to Share?
48~ Have you ever paid or been paid for 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?
30~ What's something unexpected that turns you on?
21~ What was the best date you ever went on? What has been the worst?
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…
Have you ever? Care to Share?
48~ Do you have any siblings? Are you close to your family?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
14- What's your favorite dessert? Do you a least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
51~ Are you willing to play adult games with your partner?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
*** Deal Breaker Questions ***
71~ Would you give your partner a hand or foot job? Would you receive one?
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,
Prisoner/Prison Guard Landlord/Tenant
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Escort/Client Job Applicant/Hiring Manager
13- What is the craziest/scariest thing you've ever done?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
37- Do you like your name? If you could change it, what would you change it too?