What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 01:38
19~ Who/when was your first “heartbreak”?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
3- What Superhero or Superpower would you want to be/have?
Which bands became massively popular for covering songs rather than recording originals?
* Give a rating for each one (0-100)
Over time has your thoughts on sex changed?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How can someone feel more FTM when AMAB?
82~ Do you have any fantasies involving Role-Playing?
3- What’s your favorite smell? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
15~ Have you ever been “in love”? Who? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
34~ Do you like the lights on or off during sex?
Can you share a picture of your favorite outfit and explain why you love it?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Nothing too Serious
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
I want to touch my sister’s boobs. What do I say?
17- Have you ever done drugs? Which ones? How often?
How many partners have you had oral sex with? Who? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
What was your best sex experience that still makes you horny?
12- What is the weirdest thing you've ever eaten?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
32- What's your greatest talent? Can I see it right now?
What are the ten cars that make me no longer feel inferior?
9- If you could have three wishes, what would they be? Why?
Do you have a favorite? Is it ok if your partner does?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
What is the Replika app, and how does it work?
83~ How do you feel about Porn?
What do you dislike about me? I asked you to be 100% honest.
92~ Everyone needs a “safe” word. What is yours?
Northern Lights Alert: 8 States May See Aurora Borealis Monday Night - Forbes
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
*** What’s Your Favorite…? ***
Why did McLaren hope that the Ferrari pair would pit twice during the Italian Grand Prix?
61~ How willing would you be to try new sexual positions?
9- Is there something you’ve always wanted to ask me but you’re afraid?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Is it true that Jehovah's witnesses once thought the world would end in 1975?
How about if they talk dirty and/or call you names?
Prisoner/Prison Guard Landlord/Tenant
19- What’s your favorite fairytale? What’s your least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you like it when they show and tell you what they want?
67~ Do you like it when your partner moans and/or is vocal during sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
I would allow you to do it… What would you do to me?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
36~ What is your favorite time of day to have sex/make love?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
10- What is your favorite family tradition? What’s your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
47~ What would be your dream job and why?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Would you mind if your partner watched it? How about together vs alone?
49~ How many times have you been married? Why did they end?
29~ What are some things that turn you off? What is your biggest turn off?
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?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If you win, what will you make them do?
*** Random Questions ***
1- What was your first impression of me? Has it changed?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
30~ What's something unexpected that turns you on?
How many times do you think you have “made love”?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
The Ice Breaker Questions
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
62~ Have you used adult toys?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
28~ What are some things that turn on? What is your biggest turn on?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
81~ Do you have any kinks and/or fetishes?
51~ What tends to bring a smile to your face?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
If yes, what?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
33- If you could visit any time period, when would you pick? Please explain why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
7-What do I do in bed that drives you wild? How about, what turns you off?
Would /have you ever given your partner a lap dance and Striptease?
What was the longest? What was the shortest?
Nurse/Patient Celebrity/Fan
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
10~ How many dates are necessary before you to have sex with someone?
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Escort/Client Job Applicant/Hiring Manager
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
70~ Would/do you have/like anal sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
60~ How important is oral sex? Do you like receiving? Do you like giving?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
48~ Do you have any siblings? Are you close to your family?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Any that are a turn off?
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)
1~ How old were you when you had your first kiss? Who? Care to Share?
4- For a pet, Cat, dog or other?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Model/Photographer Police/Criminal
8- What are your thoughts on politics?
26~ What side of the bed do you sleep on?
29- How superstitious are you?
42~ What’s your biggest regret in life?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Master/Slave Boss/Maid
7- What are your thoughts on religion? Is there an afterlife?
Have you ever? Care to Share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
*** Deal Breaker Questions ***
36- Do you play video games? What is your favorite? Do you a least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What would you say to prove to yourself that it was really you?
How old are you? Male or Female?
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?
What have you learned about yourself that you did not before this?
52~ What are your hobbies?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
If NO, would you ever have one? Would it be with 2 men or 2 women?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
23- What is your dream job? What was it as a child?
Teacher/Student Stranger/One Night Stand
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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Family Relation Age Play
18- What’s your favorite way to relax after a long day? What’s your least favorite?
That one or two things that made you go hmmmm, OMG or wow!
20- What’s your favorite candy? 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?
53~ How much can you tell me about the one thing you are most passionate about?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
2- What’s your favorite color? Do you a least favorite?
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…
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Please share Did you stop?
Get this wrong and this could mean the end… :-) some funny, some not…
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
84~ How do you feel about reading/listening to adult stories?
28- What are some things that people do that irritate you?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Would you read them together?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Repairman/Lonely Wife Virgin/Experienced
14- What's your favorite dessert? Do you a least favorite?
Does the thought excite you? Care to share?
17- What’s your favorite holiday? What’s your least favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
27- What was/ is nickname? Does it have a meaning behind it?
22- What is your favorite childhood memory? What is your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
5- Have you ever been hypnotized? Would you allow yourself to be?
8- What's your favorite flavor of ice cream? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
11- How about if they like a certain sports team? 12-How about drinking too much?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
11~ Have you ever been caught by your parents or children or others while having sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Doctor/Nurse Stripper/Client
22- Do you have any birth marks? How about scars? Care to share how you got them?
What have you learned about me that was new and/or surprising?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would you ever want to be woken up with oral and/or intercourse?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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…
If you say it, I will stop, and we can talk about it when you are ready.
What is your view on sex? Meaning, When/Where/ How often/
89~ Do you like taking showers together?
(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…)
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
Do you watch it? What is your 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,
40~ What’s the weirdest place you’ve ever had sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
How well do you know me? And some of your thoughts about me
15- What bad habit do you wish you could quit? Do you have any addictions?
*** Questions about Relationships/Past ***
What is your favorite toy? Ever wanted to try a specific toy?
25~ How do you feel about PDA? (Public Display of Affection)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Do you think this brought you closer together?
92~ Have you ever had or have an STD? How many? What was it?
12- What’s your favorite food? What’s your least favorite?
37- Do you like your name? If you could change it, what would you change it too?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
1- What’s your favorite animal? 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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
51~ Are you willing to play adult games with your partner?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
38~ Share your most embarrassing sexual memory?
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?
31- If given a chance to be immortal, would you take it? Why?
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?
Would you allow me to clean every part of your body with my soapy hands and fingers?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Would you do it again, and would you rather 2 females or 2 males?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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?
52~ Are you willing to make “those types” of bets with your partner?
10- List 5 of your top pet peeves.
13- What is the craziest/scariest thing you've ever done?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
*** Questions About Me ***
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
48~ Have you ever paid or been paid for sex?
39~ What are your love languages?
18- How often do you drink alcohol? What is your favorite drink?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
33- Beach or Mountains? Or is there another place to like better?
5~ When you first started having sex, was it what you thought it would be?
21~ What was the best date you ever went on? What has been the worst?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
13- What’s your favorite drink? What’s your least favorite?
18~ Who/when was your first “crush”?
76~ Have you had a threesome? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
58~ Have you ever taken Nude or Hard-core photos and/or videos? 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?
13~ Is there a difference between, making love, having sex, and fucking?
What is your favorite position? Why?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
44~ Care to share something about yourself that no one else knows about you?
Any that are a turn off?
50~ How many children do you have? What are their ages?
9~ How many times over your lifetime do you think you have had sex so far?
13- How about having a certain hair cut/style?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
Can you Deep Throat? Do you like the taste of yourself?
You know that I will be 100% truthful, so ask.
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?