The best dirty questions to ask your girlfriend are playful, a little suggestive and easy to answer. A question like “What’s something I do that you secretly find hot?” works because she can reply with one word or a whole story, as bold or as shy as she likes. Start with the flirty ones, move to the naughtier ones once she’s enjoying the game, and let her skip anything she doesn’t want to answer. Man’s Guide to Sexting, a program in The Coach app, teaches you to flirt like this over text and to read what her answers tell you.
Show me where to startPick the kind that fits her mood and how long you’ve been together. Any of these questions sounds more like you once you add a detail only the two of you know.
These six habits keep dirty questions a game you both enjoy, not a test she has to pass.
A dirty question is only half of the game. What you say after her answer decides whether she wants to keep playing.
Man’s Guide to Sexting covers what her replies can mean, from a shy “maybe” to a clear “not now,” and how to answer each one. The quiz asks a few questions, and your answers shape a personal plan.
Start with a playful question. Her answers will show you how far she wants to go.
Man’s Guide to Sexting is a 14-lesson program in The Coach app that you read whenever it suits you. It goes from a first flirty text to sexting and carrying the mood into the evening, with lessons on what to write and how to read her replies.
How to offer two versions of a message, a sweet one and a bolder one, so she can set the tone with one word.
How to share an idea in a line or two and leave room for her to shape it, instead of writing the whole scene for her.
How to tell a playful “behave” from a real “I’m busy,” and how to answer both without pushing her.
Answer a few questions to get a personal plan that shows you where to start.
Dirty Would You Rather questions make a simple game for two: every question already comes with two answers, so all you do is pick one and explain why. Keep both options tempting, since the fun is in choosing between two good things: “Would you rather go out for dinner and skip dessert, or stay in and skip dinner?” or “Would you rather take the lead tonight, or let me?”
They work over text and in person. Take turns asking and add your own questions as you go: “Would you rather I whisper what I’m thinking during dinner, or text it to you from across the table?” or “Would you rather have a night with no phones or a morning with nowhere to be?” If either of you hesitates, move on to the next one.
If the questions turn into sexting, our guide on how to sext a girl shows you how to keep it going.
When you’ve only been on a few dates, you don’t know yet how she feels about sexual talk or how fast she likes things to move. Keep the first questions flirty rather than dirty, and ask them once she’s already flirting with you: “Are you the type who makes the first move, or the type who waits for it?” or “Be honest: did you want me to kiss you on our first date?”
Before anything more daring, ask in a way that’s easy to turn down: “Can I ask you something a little less innocent, or is it too soon?” If she says yes, keep it playful; if she says it’s too soon, take it lightly and stay with easier questions. That’s how she learns she can trust you with more later.
For texts that build tension between dates, read our guide on how to tease a girl over text.
These figures come from a survey of The Coach users after their first four weeks. They show what users reported, not a result every man will see.
A list gives you a place to start, but the questions she’ll enjoy most come from your life together: a trip where it rained every day or something she said on your first date. Man’s Guide to Sexting teaches you to turn details like these into messages that could only come from you.
Reviews from men using the app.
“The program also emphasizes understanding a partner’s needs through communication, emotional connection, and attentiveness. Instead of offering quick fixes, it encourages men to slow down, listen actively, and create a more collaborative experience with their partner.”
“I’m happy to say this app has helped me open up a whole new line of communication with my S/O. Every resource for a better relationship is at your fingertips in this app. love it”
“I am grateful for the reminders and techniques to enhance and revitalize my love for my wife. Technique that makes you own the confidence that you’re doing the right stuff. Anatomy that we forgot about and sensory stuff that makes her squirm. Thank you”
“After only five or six lessons, I was tuned in to making the experience more pleasurable for her, which actually made me feel sexier! I’m not ashamed to admit that the Coach made me a better partner and lover.”
The Coach works with clinical researchers, certified sex therapists and medical professionals, including practicing urologists.
Dr. Justin Lehmiller
PhD in social psychology and senior research fellow at the Kinsey Institute.
Dr. Jessica Yih
Urologist and director of women's sexual health and male infertility at UCI.
Dr. Kirti S. Patel
Board-certified ob/gyn and host of The Gynarchy, a women's-health podcast.
Cameron Fraser
Australia's leading men's sex coach, specializing in male sexual wellness and performance.
Dr. Paula Hall
Accredited sexual and relationship psychotherapist, registered with leading professional bodies in psychotherapy.
Natalie Goldberg
Certified sex and family therapist dedicated to improving intimate relationships and personal well-being.
Dr. Justin Houman
MD, UCLA-trained urologist and male reproductive specialist focusing on sexual health.
Dr. Amy Pearlman
Board-certified urologist specializing in male sexual wellness, performance, and hormonal health.
Short ones she can answer in a line: “Couch or bed tonight?” or “What’s on your mind right now? First answer, no editing.” Send the more personal ones when you know she’s alone, and don’t expect an instant reply if she’s busy.
Ask only once she’s flirting with you, start light and give her an easy way to pass. Questions about what she enjoys with you feel playful; questions that rate her body or dig into her past feel like pressure. If she pulls back, respect that and keep things friendly.
Questions about her exes or her sexual past, questions that compare her with anyone, and anything you wouldn’t want to answer yourself. A question that would embarrass her if someone saw her screen can wait until you’re alone.
Let it go; she doesn’t owe you a reason. A simple “No problem, next one” keeps things fun. If saying no costs her nothing, she’ll find it easier to say yes when she’s in the mood.
Yes, and that may be the best part. Her answers show you what she enjoys, what she’s curious about and what she’d rather skip. Later, when you’re both relaxed, you can ask how the game felt for her and whether she’d like it softer or bolder next time.
Yes. After years together it’s easy to assume you know all her answers, and a question can still surprise you both. Mix them with ordinary conversation, though: if every message turns sexual, the dirty ones lose their charm.
Follow her answers. When she answers boldly, asks you questions back or adds details of her own, you can tell her a little more plainly what you want and keep some of it for later. Her next reply shows you whether to keep going. If she brings the chat back to everyday things, follow her and try another time.
