What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 04:40
Would /have you ever given your partner a lap dance and Striptease?
13~ Is there a difference between, making love, having sex, and fucking?
19~ Who/when was your first “heartbreak”?
What is the sum of X+XX+XXX+XXXX?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
17- Have you ever done drugs? Which ones? How often?
Nothing too Serious
If you were a writer for HBO, how would you rewrite the final season of Game of Thrones?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
22- Do you have any birth marks? How about scars? Care to share how you got them?
36- Do you play video games? What is your favorite? Do you a least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
3- What’s your favorite smell? Do you a least favorite?
Are female judges more lenient than male ones?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
*** Random Questions ***
Why do Muslims invade Western society?
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
52~ What are your hobbies?
Why does my private parts itch so much during certain periods?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
2- What’s your favorite color? Do you a least favorite?
What would you say to prove to yourself that it was really you?
In the TV show Supernatural, why is God portrayed as cruel?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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,
65~ Describe the best orgasm you’ve ever had? Care to share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
29- How superstitious are you?
Do conservative white women like black men?
83~ How do you feel about Porn?
14- What's your favorite dessert? Do you a least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Can you Deep Throat? Do you like the taste of yourself?
What is your view on sex? Meaning, When/Where/ How often/
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…
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
15~ Have you ever been “in love”? Who? Care to Share?
King Charles III pays respects to Air India crash victims at his annual birthday parade - PBS
* Give a rating for each one (0-100)
I would allow you to do it… What would you do to me?
4- For a pet, Cat, dog or other?
Why are Boomers so vehemently opposed to student loan forgiveness?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
If a narcissist can't feel remorse, can they ever feel regret for an evil act after going to rehab?
*** Deal Breaker Questions ***
62~ Have you used adult toys?
Escort/Client Job Applicant/Hiring Manager
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?
Nurse/Patient Celebrity/Fan
What was the longest? What was the shortest?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
1~ How old were you when you had your first kiss? Who? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
8- What's your favorite flavor of ice cream? Do you a least favorite?
51~ What tends to bring a smile to your face?
25~ How do you feel about PDA? (Public Display of Affection)
14- What is an embarrassing moment in your life? How about your most embarrassing?
That one or two things that made you go hmmmm, OMG or wow!
Do you like it when they show and tell you what they want?
What is your favorite toy? Ever wanted to try a specific toy?
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?
76~ Have you had a threesome? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
11~ Have you ever been caught by your parents or children or others while having sex?
Master/Slave Boss/Maid
Get this wrong and this could mean the end… :-) some funny, some not…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
5- Have you ever been hypnotized? Would you allow yourself to be?
11- How about if they like a certain sports team? 12-How about drinking too much?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
12- What’s your favorite food? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
*** Questions About Me ***
18~ Who/when was your first “crush”?
70~ Would/do you have/like anal sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
42~ What’s your biggest regret in life?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
10~ How many dates are necessary before you to have sex with someone?
28~ What are some things that turn on? What is your biggest turn on?
21~ What was the best date you ever went on? What has been the worst?
34- Ever been to a concert? What was your favorite? Who would you like to see?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
53~ How much can you tell me about the one thing you are most passionate about?
5~ When you first started having sex, was it what you thought it would be?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
22- What is your favorite childhood memory? What is your least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What have you learned about me that was new and/or surprising?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
3- What Superhero or Superpower would you want to be/have?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
6- Do you have dreams? Can you remember them? What do you usually dream about?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
18- What’s your favorite way to relax after a long day? What’s your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
27- What was/ is nickname? Does it have a meaning behind it?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
48~ Have you ever paid or been paid for sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
19- Do/have you smoked? What do you prefer? How often?
18- How often do you drink alcohol? What is your favorite drink?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
What do you dislike about me? I asked you to be 100% honest.
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?
44~ Care to share something about yourself that no one else knows about you?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
71~ Would you give your partner a hand or foot job? Would you receive one?
9- Is there something you’ve always wanted to ask me but you’re afraid?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
80~ Share your top three fantasies/desires. (Be detailed) 😊
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
26~ What side of the bed do you sleep on?
21- What's your favorite way to spend a weekend or time off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Does the thought excite you? Care to share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
40~ What’s the weirdest place you’ve ever had sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
12- What is the weirdest thing you've ever eaten?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
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- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Over time has your thoughts on sex changed?
The Ice Breaker Questions
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Do you think this brought you closer together?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
9- If you could have three wishes, what would they be? Why?
34~ Do you like the lights on or off during sex?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you read them together?
89~ Do you like taking showers together?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
If yes, what?
Will you cheat again? How can, you be sure? Define what cheating is to you.
If you win, what will you make them do?
19- What’s your favorite fairytale? What’s your least favorite?
1- What was your first impression of me? Has it changed?
Do you like the “69” position? Do you prefer to be on top or bottom?
7-What do I do in bed that drives you wild? How about, what turns you off?
29~ What are some things that turn you off? What is your biggest turn off?
1- What’s your favorite animal? Do you a least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
33- Beach or Mountains? Or is there another place to like better?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Model/Photographer Police/Criminal
Would you ever want to be woken up with oral and/or intercourse?
How old are you? Male or Female?
7- What if a person smells a certain way? 8- How about smoking?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
32- What's your greatest talent? Can I see it right now?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
49~ How many times have you been married? Why did they end?
What have you learned about yourself that you did not before this?
How many times do you think you have “made love”?
13- How about having a certain hair cut/style?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
84~ How do you feel about reading/listening to adult stories?
51~ Are you willing to play adult games with your partner?
17- What’s your favorite holiday? What’s your least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
*** Questions about Relationships/Past ***
Please share Did you stop?
11- List at least 5 things on your bucket list. Have you done any of them already?
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Teacher/Student Stranger/One Night Stand
10- List 5 of your top pet peeves.
81~ Do you have any kinks and/or fetishes?
9~ How many times over your lifetime do you think you have had sex so far?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
31- If given a chance to be immortal, would you take it? Why?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Any that are a turn off?
If NO, would you ever have one? Would it be with 2 men or 2 women?
92~ Everyone needs a “safe” word. What is yours?
Do you have a favorite? Is it ok if your partner does?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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 allow me to clean every part of your body with my soapy hands and fingers?
*** What’s Your Favorite…? ***
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
92~ Have you ever had or have an STD? How many? What was it?
20- What’s your favorite candy? What’s your least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
38~ Share your most embarrassing sexual memory?
Doctor/Nurse Stripper/Client
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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…
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
82~ Do you have any fantasies involving Role-Playing?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
36~ What is your favorite time of day to have sex/make love?
What is your favorite position? Why?
Any that are a turn off?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
23- What is your dream job? What was it as a child?
Do you watch it? What is your favorite?
39~ What are your love languages?
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)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
How well do you know me? And some of your thoughts about me
If you say it, I will stop, and we can talk about it when you are ready.
7- What are your thoughts on religion? Is there an afterlife?
Would you do it again, and would you rather 2 females or 2 males?
Family Relation Age Play
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How about if they talk dirty and/or call you names?
30~ What's something unexpected that turns you on?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
61~ How willing would you be to try new sexual positions?
(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…)
8- What are your thoughts on politics?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Prisoner/Prison Guard Landlord/Tenant
If you lose, are you willing to be their sex slave for a day, (anything goes)?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Repairman/Lonely Wife Virgin/Experienced
64~ When was your very first orgasm? When was your first from having sex? Care to share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
13- What is the craziest/scariest thing you've ever done?
Have you ever? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Would you mind if your partner watched it? How about together vs alone?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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?
50~ How many children do you have? What are their ages?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
13- What’s your favorite drink? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
47~ What would be your dream job and why?
You know that I will be 100% truthful, so ask.