What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 12:12
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
17- Have you ever done drugs? Which ones? How often?
The Ice Breaker Questions
What are your darkest taboo confessions?
Would you read them together?
14- What's your favorite dessert? Do you a 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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
I would allow you to do it… What would you do to me?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Have you made a female relative or friend squirt?
3- What’s your favorite smell? Do you a least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
*** Questions about Relationships/Past ***
39~ What are your love languages?
Who is the most annoying character in the Office?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
36~ What is your favorite time of day to have sex/make love?
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53~ How much can you tell me about the one thing you are most passionate about?
34~ Do you like the lights on or off during sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Get this wrong and this could mean the end… :-) some funny, some not…
What are some common historical misconceptions?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
What type of fish is best for fish tacos?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
3- What Superhero or Superpower would you want to be/have?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Why do I feel so tired all the time even after a good night’s sleep?
33- Beach or Mountains? Or is there another place to like better?
84~ How do you feel about reading/listening to adult stories?
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?
What is the problem between Turkey and Greece?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Do you suck dicks with no reciprocation?
What have you learned about me that was new and/or surprising?
76~ Have you had a threesome? 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?
What did your sister do to you that you can never forget?
What have you learned about yourself that you did not before this?
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,
11- What's your favorite restaurant? What’s your least favorite?
What are the extra benefits of a smart TV?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
Do you like the “69” position? Do you prefer to be on top or bottom?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
Would you allow me to clean every part of your body with my soapy hands and fingers?
If you say it, I will stop, and we can talk about it when you are ready.
36- Do you play video games? What is your favorite? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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?
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…
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)
*** Deal Breaker Questions ***
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
13~ Is there a difference between, making love, having sex, and fucking?
49~ How many times have you been married? Why did they end?
What do you dislike about me? I asked you to be 100% honest.
25~ How do you feel about PDA? (Public Display of Affection)
45~ How do you feel about me blindfolding you? How about blindfolding me?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Do you think this brought you closer together?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
82~ Do you have any fantasies involving Role-Playing?
71~ Would you give your partner a hand or foot job? Would you receive one?
6- Do you have dreams? Can you remember them? What do you usually dream about?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Nothing too Serious
28~ What are some things that turn on? What is your biggest turn on?
How many times do you think you have “made love”?
48~ Have you ever paid or been paid for sex?
(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…)
Would you mind if your partner watched it? How about together vs alone?
30~ What's something unexpected that turns you on?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
48~ Do you have any siblings? Are you close to your family?
How many partners have you had oral sex with? Who? Care to Share?
* Give a rating for each one (0-100)
15~ Have you ever been “in love”? Who? Care to Share?
38~ Share your most embarrassing sexual memory?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
29- How superstitious are you?
That one or two things that made you go hmmmm, OMG or wow!
Please share Did you stop?
*** What’s Your Favorite…? ***
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
20- What’s your favorite candy? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Prisoner/Prison Guard Landlord/Tenant
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
29~ What are some things that turn you off? What is your biggest turn off?
How well do you know me? And some of your thoughts about me
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would you do it again, and would you rather 2 females or 2 males?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
If you win, what will you make them do?
Repairman/Lonely Wife Virgin/Experienced
Can you Deep Throat? Do you like the taste of yourself?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
13- What is the craziest/scariest thing you've ever done?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
32- What's your greatest talent? Can I see it right now?
1~ How old were you when you had your first kiss? Who? Care to Share?
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?
2- What’s your favorite color? Do you a least favorite?
What is your favorite position? Why?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
1- What was your first impression of me? Has it changed?
Over time has your thoughts on sex changed?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
52~ Are you willing to make “those types” of bets with your partner?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
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…
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What was the longest? What was the shortest?
*** Random Questions ***
7-What do I do in bed that drives you wild? How about, what turns you off?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What is your view on sex? Meaning, When/Where/ How often/
8- What's your favorite flavor of ice cream? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
7- What are your thoughts on religion? Is there an afterlife?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Have you ever? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
9- Is there something you’ve always wanted to ask me but you’re afraid?
22- Do you have any birth marks? How about scars? Care to share how you got them?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
65~ Describe the best orgasm you’ve ever had? Care to share?
13- How about having a certain hair cut/style?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
83~ How do you feel about Porn?
23- What is your dream job? What was it as a child?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
12- What is the weirdest thing you've ever eaten?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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?
21~ What was the best date you ever went on? What has been the worst?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
11~ Have you ever been caught by your parents or children or others while having sex?
62~ Have you used adult toys?
27- What was/ is nickname? Does it have a meaning behind it?
21- What's your favorite way to spend a weekend or time off?
4- For a pet, Cat, dog or other?
What is your favorite toy? Ever wanted to try a specific toy?
5- Have you ever been hypnotized? Would you allow yourself to be?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
52~ What are your hobbies?
50~ How many children do you have? What are their ages?
Family Relation Age Play
70~ Would/do you have/like anal sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
9- What’s your favorite season and why? What’s your least favorite?
If yes, what?
12- What’s your favorite food? What’s your least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Master/Slave Boss/Maid
11- List at least 5 things on your bucket list. Have you done any of them already?
92~ Everyone needs a “safe” word. What is yours?
How old are you? Male or Female?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
15- What's your favorite saying? What word or phrase is your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
*** Questions About Me ***
13- What’s your favorite drink? What’s your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Nurse/Patient Celebrity/Fan
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you watch it? What is your favorite?
Do you like it when they show and tell you what they want?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
19- Do/have you smoked? What do you prefer? How often?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Would /have you ever given your partner a lap dance and Striptease?
How about if they talk dirty and/or call you names?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
28- What are some things that people do that irritate you?
80~ Share your top three fantasies/desires. (Be detailed) 😊
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
92~ Have you ever had or have an STD? How many? What was it?
7- What if a person smells a certain way? 8- How about smoking?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What would you say to prove to yourself that it was really you?
42~ What’s your biggest regret in life?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Doctor/Nurse Stripper/Client
10- List 5 of your top pet peeves.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
47~ What would be your dream job and why?
31- If given a chance to be immortal, would you take it? Why?
37- Do you like your name? If you could change it, what would you change it too?
18- How often do you drink alcohol? What is your favorite drink?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
You know that I will be 100% truthful, so ask.
15- What bad habit do you wish you could quit? Do you have any addictions?
17- What’s your favorite holiday? What’s your least favorite?
26~ What side of the bed do you sleep on?
9~ How many times over your lifetime do you think you have had sex so far?
10~ How many dates are necessary before you to have sex with someone?
60~ How important is oral sex? Do you like receiving? Do you like giving?
51~ What tends to bring a smile to your face?
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?
18~ Who/when was your first “crush”?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
40~ What’s the weirdest place you’ve ever had sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
51~ Are you willing to play adult games with your partner?
Model/Photographer Police/Criminal
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
Any that are a turn off?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
19~ Who/when was your first “heartbreak”?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
33- If you could visit any time period, when would you pick? Please explain why?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
5~ When you first started having sex, was it what you thought it would be?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
3- Should Pluto still be considered a planet? 4- How about smoking?
8- What are your thoughts on politics?
44~ Care to share something about yourself that no one else knows about you?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
89~ Do you like taking showers together?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
61~ How willing would you be to try new sexual positions?
9- If you could have three wishes, what would they be? Why?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Escort/Client Job Applicant/Hiring Manager
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Does the thought excite you? Care to share?
Any that are a turn off?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Do you have a favorite? Is it ok if your partner does?