What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 13:05
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
*** Questions about Relationships/Past ***
67~ Do you like it when your partner moans and/or is vocal during sex?
Why does it itch on my vulva, uterus, and sides of my vagina, but it doesn't itch inside the vagina?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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…
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Why do some men love sucking cocks?
20- What’s your favorite candy? What’s your least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
70~ Would/do you have/like anal sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
13- What is the craziest/scariest thing you've ever done?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What are some cute stories with your crush?
52~ Are you willing to make “those types” of bets with your partner?
44~ Care to share something about yourself that no one else knows about you?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
My boyfriend won’t tell me his past and it hurts me so I broke up with him what do I do?
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…
Do you shave/trim your pubic hair? For you guys do you shave your balls?
10- What is your favorite family tradition? What’s your least favorite?
What do porn stars do when they get old?
17- Have you ever done drugs? Which ones? How often?
48~ Do you have any siblings? Are you close to your family?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Fallout meets BioShock in fascinating new adventure game - GAMINGbible
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Do you watch it? What is your favorite?
My ex got into a relationship within 2 weeks after a breakup. What should I do?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
I can not sleep. what is the problem?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
71~ Would you give your partner a hand or foot job? Would you receive one?
54~ Would you ever go skinny dipping with your partner? Have you ever been? 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?
How do the youth in Taiwan perceive their national identity in relation to China?
3- Should Pluto still be considered a planet? 4- How about smoking?
Nothing too Serious
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
29~ What are some things that turn you off? What is your biggest turn off?
Repairman/Lonely Wife Virgin/Experienced
If YES, was it with 2 men or 2 women? Did you enjoy it?
8- What's your favorite flavor of ice cream? Do you a least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Over time has your thoughts on sex changed?
5~ When you first started having sex, was it what you thought it would be?
Doctor/Nurse Stripper/Client
33- Beach or Mountains? Or is there another place to like better?
Do you like the “69” position? Do you prefer to be on top or bottom?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
10~ How many dates are necessary before you to have sex with someone?
47~ What would be your dream job and why?
Model/Photographer Police/Criminal
How about if they talk dirty and/or call you names?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
32- What's your greatest talent? Can I see it right now?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Does the thought excite you? Care to share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
*** Questions About Me ***
Family Relation Age Play
9- If you could have three wishes, what would they be? Why?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Nurse/Patient Celebrity/Fan
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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,
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Any that are a turn off?
Do you have a favorite? Is it ok if your partner does?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would you do it again, and would you rather 2 females or 2 males?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
18~ Who/when was your first “crush”?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Would you mind if your partner watched it? How about together vs alone?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
11~ Have you ever been caught by your parents or children or others while having 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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
11- How about if they like a certain sports team? 12-How about drinking too much?
48~ Have you ever paid or been paid for sex?
51~ Are you willing to play adult games with your partner?
19~ Who/when was your first “heartbreak”?
You know that I will be 100% truthful, so ask.
5- Have you ever been hypnotized? Would you allow yourself to be?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
50~ How many children do you have? What are their ages?
28- What are some things that people do that irritate you?
92~ Everyone needs a “safe” word. What is yours?
What was the longest? What was the shortest?
33- If you could visit any time period, when would you pick? Please explain why?
62~ Have you used adult toys?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
82~ Do you have any fantasies involving Role-Playing?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Would you read them together?
34~ Do you like the lights on or off during sex?
What do you dislike about me? I asked you to be 100% honest.
2- What’s your favorite color? Do you a least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If you win, what will you make them do?
84~ How do you feel about reading/listening to adult stories?
15- What bad habit do you wish you could quit? Do you have any addictions?
37- Do you like your name? If you could change it, what would you change it too?
*** What’s Your Favorite…? ***
What have you learned about yourself that you did not before this?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Escort/Client Job Applicant/Hiring Manager
45~ How do you feel about me blindfolding you? How about blindfolding me?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
61~ How willing would you be to try new sexual positions?
1- What’s your favorite animal? Do you a least favorite?
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)
(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- What's your favorite restaurant? What’s your least favorite?
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
13- What’s your favorite drink? What’s your least favorite?
Prisoner/Prison Guard Landlord/Tenant
25~ How do you feel about PDA? (Public Display of Affection)
I would allow you to do it… What would you do to me?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Get this wrong and this could mean the end… :-) some funny, some not…
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?
3- What Superhero or Superpower would you want to be/have?
4- For a pet, Cat, dog or other?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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?
51~ What tends to bring a smile to your face?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Master/Slave Boss/Maid
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
*** Deal Breaker Questions ***
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
That one or two things that made you go hmmmm, OMG or wow!
7-What do I do in bed that drives you wild? How about, what turns you off?
12- What’s your favorite food? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
30~ What's something unexpected that turns you on?
22- What is your favorite childhood memory? What is your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
What would you say to prove to yourself that it was really you?
39~ What are your love languages?
What is your favorite position? Why?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
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?
Would you allow me to clean every part of your body with my soapy hands and fingers?
What have you learned about me that was new and/or surprising?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
23- What is your dream job? What was it as a child?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
*** Random Questions ***
Do you think this brought you closer together?
65~ Describe the best orgasm you’ve ever had? Care to share?
Have you ever? Care to Share?
How old are you? Male or Female?
11- List at least 5 things on your bucket list. Have you done any of them already?
27- What was/ is nickname? Does it have a meaning behind it?
Can you Deep Throat? Do you like the taste of yourself?
53~ How much can you tell me about the one thing you are most passionate about?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
7- What if a person smells a certain way? 8- How about smoking?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
21~ What was the best date you ever went on? What has been the worst?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
12- What is the weirdest thing you've ever eaten?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
What is your view on sex? Meaning, When/Where/ How often/
Would /have you ever given your partner a lap dance and Striptease?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
18- How often do you drink alcohol? What is your favorite drink?
Please share Did you stop?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
The Ice Breaker Questions
18- What’s your favorite way to relax after a long day? What’s your least favorite?
8- What are your thoughts on politics?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
83~ How do you feel about Porn?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
76~ Have you had a threesome? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
80~ Share your top three fantasies/desires. (Be detailed) 😊
21- What's your favorite way to spend a weekend or time off?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How many times do you think you have “made love”?
15~ Have you ever been “in love”? Who? Care to Share?
13- How about having a certain hair cut/style?
14- What's your favorite dessert? Do you a least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
60~ How important is oral sex? Do you like receiving? Do you like giving?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
1- What was your first impression of me? Has it changed?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
31- If given a chance to be immortal, would you take it? Why?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
How many partners have you had oral sex with? Who? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
Any that are a turn off?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Do you like it when they show and tell you what they want?
52~ What are your hobbies?
29- How superstitious are you?
10- List 5 of your top pet peeves.
3- What’s your favorite smell? Do you a least favorite?
36~ What is your favorite time of day to have sex/make love?
Teacher/Student Stranger/One Night Stand
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What is your favorite toy? Ever wanted to try a specific toy?
9~ How many times over your lifetime do you think you have had sex so far?
38~ Share your most embarrassing sexual memory?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
14- What is an embarrassing moment in your life? How about your most embarrassing?
89~ Do you like taking showers together?
19- What’s your favorite fairytale? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
42~ What’s your biggest regret in life?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
9- What’s your favorite season and why? What’s your least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
81~ Do you have any kinks and/or fetishes?
28~ What are some things that turn on? What is your biggest turn on?
If yes, what?
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?
7- What are your thoughts on religion? Is there an afterlife?
* Give a rating for each one (0-100)
6- Do you have dreams? Can you remember them? What do you usually dream about?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
19- Do/have you smoked? What do you prefer? How often?
How well do you know me? And some of your thoughts about me
36- Do you play video games? What is your favorite? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
49~ How many times have you been married? Why did they end?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
26~ What side of the bed do you sleep on?