What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 16:10
17- What’s your favorite holiday? What’s your least favorite?
44~ Care to share something about yourself that no one else knows about you?
80~ Share your top three fantasies/desires. (Be detailed) 😊
89~ Do you like taking showers together?
*** Questions About Me ***
Would you ever want to be woken up with oral and/or intercourse?
What the early "F1" movie reviews are saying ahead of New York premiere - Motorsport.com
3- What’s your favorite smell? Do you a least favorite?
How many partners have you had oral sex with? Who? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Did you swallow cum the first time you sucked a penis?
Do you have a favorite? Is it ok if your partner does?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
18~ Who/when was your first “crush”?
Reddit user surprised when 1960s computer panel emerged from collapsed family garage - Ars Technica
3- What Superhero or Superpower would you want to be/have?
37- Do you like your name? If you could change it, what would you change it too?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Did another parent ever tell you something about your child that you didn’t know?
Would you do it again, and would you rather 2 females or 2 males?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
19~ Who/when was your first “heartbreak”?
15- What's your favorite saying? What word or phrase is your least favorite?
Nothing too Serious
34~ Do you like the lights on or off during sex?
What is the most inappropriate thing your wife has done in front of you?
11- List at least 5 things on your bucket list. Have you done any of them already?
12- What’s your favorite food? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
Which is better, a naked picture of some one you know or porn videos?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
48~ Do you have any siblings? Are you close to your family?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
1~ How old were you when you had your first kiss? Who? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
10- List 5 of your top pet peeves.
22- What is your favorite childhood memory? What is your least favorite?
Can you Deep Throat? Do you like the taste of yourself?
26~ What side of the bed do you sleep on?
Has anyone shared his wife with a friend? How was it?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
21~ What was the best date you ever went on? What has been the worst?
In your opinion, who is the most overrated singer/band/artist in modern music history and why?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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)
Are judges being lenient on hard criminals?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If YES, was it with 2 men or 2 women? Did you enjoy it?
If you win, what will you make them do?
51~ Are you willing to play adult games with your partner?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
You know that I will be 100% truthful, so ask.
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?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Do you watch it? What is your favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
How old are you? Male or Female?
7- What are your thoughts on religion? Is there an afterlife?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
31- If given a chance to be immortal, would you take it? Why?
13- How about having a certain hair cut/style?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
47~ What would be your dream job and why?
1- What’s your favorite animal? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
*** Random Questions ***
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you think this brought you closer together?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
4- For a pet, Cat, dog or other?
How many times do you think you have “made love”?
6- Do you have dreams? Can you remember them? What do you usually dream about?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
32- What's your greatest talent? Can I see it right now?
61~ How willing would you be to try new sexual positions?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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,
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
8- What are your thoughts on politics?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
52~ Are you willing to make “those types” of bets with your partner?
9- What’s your favorite season and why? What’s your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
27- What was/ is nickname? Does it have a meaning behind it?
Do you like the “69” position? Do you prefer to be on top or bottom?
How about if they talk dirty and/or call you names?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Do you like it when they show and tell you what they want?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
1- What was your first impression of me? Has it changed?
5~ When you first started having sex, was it what you thought it would be?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
45~ How do you feel about me blindfolding you? How about blindfolding me?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
21- What's your favorite way to spend a weekend or time off?
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…
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
9- Is there something you’ve always wanted to ask me but you’re afraid?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
9~ How many times over your lifetime do you think you have had sex so far?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
(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…)
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
10- What is your favorite family tradition? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
15~ Have you ever been “in love”? Who? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Does the thought excite you? Care to share?
15- What bad habit do you wish you could quit? Do you have any addictions?
Please share Did you stop?
36- Do you play video games? What is your favorite? Do you a least favorite?
What have you learned about yourself that you did not before this?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Would you mind if your partner watched it? How about together vs alone?
What would you say to prove to yourself that it was really you?
12- What is the weirdest thing you've ever eaten?
9- If you could have three wishes, what would they be? Why?
Master/Slave Boss/Maid
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
What is your view on sex? Meaning, When/Where/ How often/
40~ What’s the weirdest place you’ve ever had sex?
If you say it, I will stop, and we can talk about it when you are ready.
83~ How do you feel about Porn?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
30~ What's something unexpected that turns you on?
50~ How many children do you have? What are their ages?
3- Should Pluto still be considered a planet? 4- How about smoking?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
What was the longest? What was the shortest?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
29- How superstitious are you?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Would /have you ever given your partner a lap dance and Striptease?
67~ Do you like it when your partner moans and/or is vocal during sex?
The Ice Breaker Questions
42~ What’s your biggest regret in life?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
33- Beach or Mountains? Or is there another place to like better?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
92~ Have you ever had or have an STD? How many? What was it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Any that are a turn off?
36~ What is your favorite time of day to have sex/make love?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Any that are a turn off?
38~ Share your most embarrassing sexual memory?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
82~ Do you have any fantasies involving Role-Playing?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
I would allow you to do it… What would you do to me?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
29~ What are some things that turn you off? What is your biggest turn off?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Family Relation Age Play
3- What was the most surprising thing you’ve learned about me throughout our relationship?
52~ What are your hobbies?
Would you read them together?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
14- What's your favorite dessert? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Have you ever? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
51~ What tends to bring a smile to your face?
*** Questions about Relationships/Past ***
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
18- How often do you drink alcohol? What is your favorite drink?
Over time has your thoughts on sex changed?
What is your favorite position? Why?
That one or two things that made you go hmmmm, OMG or wow!
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
60~ How important is oral sex? Do you like receiving? Do you like giving?
*** Deal Breaker Questions ***
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
*** What’s Your Favorite…? ***
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
28- What are some things that people do that irritate you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
13~ Is there a difference between, making love, having sex, and fucking?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
53~ How much can you tell me about the one thing you are most passionate about?
Model/Photographer Police/Criminal
10~ How many dates are necessary before you to have sex with someone?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What have you learned about me that was new and/or surprising?
62~ Have you used adult toys?
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…
Would you allow me to clean every part of your body with my soapy hands and fingers?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Get this wrong and this could mean the end… :-) some funny, some not…
11- How about if they like a certain sports team? 12-How about drinking too much?
11~ Have you ever been caught by your parents or children or others while having sex?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
70~ Would/do you have/like anal sex?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
22~ What is the best pickup line anyone has ever used on you? What was the worst?
71~ Would you give your partner a hand or foot job? Would you receive one?
84~ How do you feel about reading/listening to adult stories?
11- What's your favorite restaurant? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
33- If you could visit any time period, when would you pick? Please explain why?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Nurse/Patient Celebrity/Fan
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
25~ How do you feel about PDA? (Public Display of Affection)
39~ What are your love languages?
Prisoner/Prison Guard Landlord/Tenant
13- What is the craziest/scariest thing you've ever done?
48~ Have you ever paid or been paid for sex?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
7- What if a person smells a certain way? 8- How about smoking?
If yes, what?
17- Have you ever done drugs? Which ones? How often?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
19- What’s your favorite fairytale? What’s your least favorite?
76~ Have you had a threesome? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What do you dislike about me? I asked you to be 100% honest.
49~ How many times have you been married? Why did they end?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
* Give a rating for each one (0-100)
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?
8- What's your favorite flavor of ice cream? 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?
23- What is your dream job? What was it as a child?
Doctor/Nurse Stripper/Client
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.