What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 06:56
52~ What are your hobbies?
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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How do you fight the push and pull (manipulation) tactic if you want to win him?
Model/Photographer Police/Criminal
76~ Have you had a threesome? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
9- What’s your favorite season and why? What’s your least favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Has anyone ever participated in a gang bang and what was it like?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
You know that I will be 100% truthful, so ask.
Are there girls here who like group sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What was the longest? What was the shortest?
What's wrong with white women?
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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
What’s a historical event you wish more people talked about?
61~ How willing would you be to try new sexual positions?
13- How about having a certain hair cut/style?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
How can people balance religious beliefs with seeking professional mental health care?
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?
11- How about if they like a certain sports team? 12-How about drinking too much?
53~ How much can you tell me about the one thing you are most passionate about?
Why is my ex still keeping in touch with me even though she dumped me?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
21- What's your favorite way to spend a weekend or time off?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Can I use the LEG PRESS to build muscle?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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- Beach or Mountains? Or is there another place to like better?
What’s the craziest thing you’ve heard pretending to be asleep?
9- If you could have three wishes, what would they be? Why?
47~ What would be your dream job and why?
Nurse/Patient Celebrity/Fan
Red Dead Redemption's John Marston Actor Teases "Exciting News" Coming Soon - GameSpot
84~ How do you feel about reading/listening to adult stories?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
10- What is your favorite family tradition? What’s your least favorite?
How old are you? Male or Female?
19- Do/have you smoked? What do you prefer? How often?
20- What’s your favorite candy? What’s your least favorite?
Why do some people believe that Homelander would be no match for Superman or Thor?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
18~ Who/when was your first “crush”?
15~ Have you ever been “in love”? Who? Care to Share?
How can we become the best humans? How can we trust each other?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What have you learned about me that was new and/or surprising?
Would you do it again, and would you rather 2 females or 2 males?
92~ Have you ever had or have an STD? How many? What was it?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
15- What bad habit do you wish you could quit? Do you have any addictions?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
50~ How many children do you have? What are their ages?
28- What are some things that people do that irritate you?
What have you learned about yourself that you did not before this?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
15- What's your favorite saying? What word or phrase is your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
The Ice Breaker Questions
46~ Have you ever used furniture, or other types of things to aid you while having sex?
34~ Do you like the lights on or off during sex?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
10~ How many dates are necessary before you to have sex with someone?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
42~ What’s your biggest regret in life?
7- What if a person smells a certain way? 8- How about smoking?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
89~ Do you like taking showers together?
What would you say to prove to yourself that it was really you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
3- What’s your favorite smell? Do you a least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
25~ How do you feel about PDA? (Public Display of Affection)
18- How often do you drink alcohol? What is your favorite drink?
27- What was/ is nickname? Does it have a meaning behind it?
45~ How do you feel about me blindfolding you? How about blindfolding me?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
23- What is your dream job? What was it as a child?
Family Relation Age Play
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
1- What’s your favorite animal? Do you a least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
60~ How important is oral sex? Do you like receiving? Do you like giving?
13- What’s your favorite drink? What’s your least favorite?
17- Have you ever done drugs? Which ones? How often?
Doctor/Nurse Stripper/Client
29~ What are some things that turn you off? What is your biggest turn off?
44~ Care to share something about yourself that no one else knows about you?
67~ Do you like it when your partner moans and/or is vocal during sex?
3- What Superhero or Superpower would you want to be/have?
13- What is the craziest/scariest thing you've ever done?
30~ What's something unexpected that turns you on?
How many partners have you had oral sex with? Who? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Would you read them together?
Have you ever? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Do you like it when they show and tell you what they want?
7- What are your thoughts on religion? Is there an afterlife?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
14- What's your favorite dessert? Do you a least favorite?
How well do you know me? And some of your thoughts about me
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
4- For a pet, Cat, dog or other?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
10- List 5 of your top pet peeves.
(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…)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Over time has your thoughts on sex changed?
*** Random Questions ***
Can you Deep Throat? Do you like the taste of yourself?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
What is your favorite toy? Ever wanted to try a specific toy?
12- What’s your favorite food? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
Would you allow me to clean every part of your body with my soapy hands and fingers?
How about if they talk dirty and/or call you names?
Do you have a favorite? Is it ok if your partner does?
If you win, what will you make them do?
7-What do I do in bed that drives you wild? How about, what turns you off?
I would allow you to do it… What would you do to me?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Teacher/Student Stranger/One Night Stand
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
8- What are your thoughts on politics?
37- Do you like your name? If you could change it, what would you change it too?
31- If given a chance to be immortal, would you take it? Why?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
Master/Slave Boss/Maid
Escort/Client Job Applicant/Hiring Manager
19~ Who/when was your first “heartbreak”?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
51~ What tends to bring a smile to your face?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Do you watch it? What is your favorite?
5~ When you first started having sex, was it what you thought it would be?
Any that are a turn off?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
29- How superstitious are you?
49~ How many times have you been married? Why did they end?
92~ Everyone needs a “safe” word. What is yours?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Do you think this brought you closer together?
38~ Share your most embarrassing sexual memory?
12- What is the weirdest thing you've ever eaten?
What is your view on sex? Meaning, When/Where/ How often/
2- What’s your favorite color? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
58~ Have you ever taken Nude or Hard-core photos and/or videos? 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?
13~ Is there a difference between, making love, having sex, and fucking?
52~ Are you willing to make “those types” of bets with your partner?
62~ Have you used adult toys?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would /have you ever given your partner a lap dance and Striptease?
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.
81~ Do you have any kinks and/or fetishes?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
39~ What are your love languages?
Please share Did you stop?
9~ How many times over your lifetime do you think you have had sex so far?
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?
How many times do you think you have “made love”?
*** Deal Breaker Questions ***
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you like the “69” position? Do you prefer to be on top or bottom?
If YES, was it with 2 men or 2 women? Did you enjoy it?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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)
6- Do you have dreams? Can you remember them? What do you usually dream about?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
36~ What is your favorite time of day to have sex/make love?
32- What's your greatest talent? Can I see it right now?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
1- What was your first impression of me? Has it changed?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
17- What’s your favorite holiday? What’s your least favorite?
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,
83~ How do you feel about Porn?
28~ What are some things that turn on? What is your biggest turn on?
70~ Would/do you have/like anal sex?
40~ What’s the weirdest place you’ve ever had sex?
51~ Are you willing to play adult games with your partner?
*** What’s Your Favorite…? ***
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
11- What's your favorite restaurant? What’s your least favorite?
Nothing too Serious
33- If you could visit any time period, when would you pick? Please explain why?
*** Questions about Relationships/Past ***
What do you dislike about me? I asked you to be 100% honest.
If yes, what?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
48~ Have you ever paid or been paid for sex?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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?
Get this wrong and this could mean the end… :-) some funny, some not…
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
* Give a rating for each one (0-100)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Prisoner/Prison Guard Landlord/Tenant
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
26~ What side of the bed do you sleep on?
What is your favorite position? Why?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
11~ Have you ever been caught by your parents or children or others while having sex?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would you mind if your partner watched it? How about together vs alone?
Any that are a turn off?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
5- Have you ever been hypnotized? Would you allow yourself to be?
Does the thought excite you? Care to share?
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?
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…
11- List at least 5 things on your bucket list. Have you done any of them already?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
48~ Do you have any siblings? Are you close to your family?
*** Questions About Me ***
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…