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How To Have Sexual Conversations 

by Ruby

On a date, it’s important to ask questions that help uncover each other’s interests and values. But if you only stick to friendly topics, you only get friendly connections.

You need to start asking more sex-oriented questions on your dates. 

This involves subjects such as romance, attraction, flirting, sexuality, and previous sexual experiences.

But before I teach you how to talk sexual with a woman, I’ll share a story about how I learned to have a more sexy mindset.

A Rocky Start

“My friend and I just made a bet and we want you to settle it. Who do you think masturbates more — men or women?”

I’d just read some pick-up advice that told me to approach girls in bars with that question. And I was positive I was going to get slapped that night.

The women we were talking to stared back in disbelief and laughed nervously. One of them scoffed, “Are you serious right now? Why are you even asking us that?”

I was mortified. I felt ashamed. I stumbled over my words trying to explain myself, “Umm..I’m not trying to be weird. I’m sorry if it came off like that.”

They told me how it was weird and they weren’t going to answer a question like that. I apologized and walked away back to my friend.

I figured I must be doing something wrong. So I tried again with another group, and then another. I kept getting the same negative reactions.

After downing a drink (or two), I decided to try again with another group. They initially gave me the same attitude, but this time the liquid courage gave me a comeback.

With a tipsy grin I shot back, “Oh please, we’re all adults here. We all do it, it’s not a big deal.”

As I awaited the wrath of three women, I was surprised to hear them laughing and sharing their opinions. They even began debating each other and trying to argue their viewpoints playfully to me.

After a couple of minutes, we were all introducing ourselves and hitting it off like old friends.

Why did women suddenly respond with enthusiasm rather than distaste?

Embracing Your Sexuality So She Can Embrace Hers

Whether it’s friends, family, religion, or media — many of us were raised to think that expressing our sexual interest (flirting) was wrong. This manifests in us as sexual shame.

This is especially true for many women who are afraid of being seen as “slutty” or too forward. Because of this, women often won’t signal their interest first. And they won’t talk about anything sexual until you do.

In the above story, I finally embraced my sexuality and made the topic of sex out to be fun and no big deal. Because of that, the women felt more comfortable and confident about embracing their own sensual side.

Deep down, women want and desire sex with the right person, just like men. Sexual intimacy is at the core of our psychological needs.

But to consider having sex with you, a woman has to think about sex — especially with you. She can only do that if you show her that sexual conversations aren’t shameful.

Your attitude has to convey that they’re a healthy part of building a romantic connection.

I’m not expecting you walk up to random women with questions women like that. That was just me in my silly “pickup artist” days. In fact, I’ve found that while that approach can work, you usually get a much stronger response and connection if you wait until later in the conversation.

So let’s talk about how you can bring up these types of questions naturally on a first or second date.

Flying Into The Danger Zone

Guys always ask, “Won’t it be weird if I randomly ask her a sexual question?”

Let’s get this straight once and for all…

NO.

If you’re lucky enough to already be chatting about a subject related to sex like past dates, previous relationships, or online dating – then of course that’ll feel the most natural. But you can’t count on that. So…

Stop waiting for the perfect moment to move into intimate topics. There isn’t one. 

We all eventually have to take a leap of faith to ask more personal questions and get to know someone.

Unfortunately, very few women are going to lead it there or say “You can ask me about sex now!” But if you have the courage to take a shot, women will often get excited to continue exploring these discussions.

Just assume if you’ve been talking for a minimum of 15-30 minutes (on a date or at a bar), a simple segue is all you need. Such as…

  • “Let me ask you a personal question…”
  • “So, tell me the truth…”
  • “Okay, so now that we’ve gotten the small talk out of the way, I want to get to know the real you…”
  • “Can I ask you something more forward?”
  • “Tell me something fun about yourself…”

This will get her ready for a more vulnerable conversation. From there, you can roll into your first sexual question. 

Getting To The Good Stuff

Review the examples below and pick a few that you are genuinely curious about. 

Of course, you don’t want to start with something extremely intimate. That will come off as intense and discourage a woman from opening up.

Start with lighter questions. If she’s discussing them with you, you can move towards heavier ones. It’s fine to wait until you have a bit more rapport in the conversation and sometimes even wait until the second date.

Light

  • “What qualities make a man instantly attractive to you?”
  • “How comfortable are you with public affection?”
  • “When was your first kiss?”
  • “What was your first kiss like?”
  • “What do you think you look sexiest in?”
  • “How do you flirt with a guy when you want to show him you’re interested?”
  • “Have you ever made the first move with a guy? What was it?”
  • “Do you believe in the concept of soul mates or true love?”
  • “Are there any topics of conversation that catch your attention and make you more interested in a man?”
  • “Do you prefer to be the pursuer or the pursued?”
  • “What do you think is the biggest mistake people make when they flirt?”
  • “What are your favorite ways to flirt?”
  • “Do you have a preference for subtle or outright flirting?”
  • “How do you like to express your affection to someone you truly care about?”
  • “Have you ever met someone who you felt an immediate connection with?”
  • “What would constitute a dream date for you?”
  • “What type of physical touch do you find the most arousing?”
  • “What sparks a strong connection for you when you meet someone new?”
  • “Are you more attracted to looks or personality?”
  • “Have you ever had a crush on someone you worked with?”
  • “What are your favorite physical features in a man?”
  • “Describe the best kiss that you’ve ever experienced.”
  • “What kind of romantic gestures make you feel special?”
  • “What do you think is the key to a successful and intimate relationship?”
  • “What is an important lesson you’ve learned from past relationships?”
  • “What is the most romantic thing any man has ever done for you?”
  • “How important is physical attraction to you in a relationship?”

Medium

  • “Have you ever gone skinny-dipping?”
  • “Have you ever had a friend with benefits?”
  • “What unexpected place do you love being touched?”
  • “How important is a passionate sexual connection to you in a relationship?”
  • “Do you consider yourself a sexual person?”
  • “When was the first time you had sex?”
  • “Would you ever sleep with someone on a first date if the connection was strong enough?”
  • “What are your thoughts on sex on the first date?”
  • “What do you look for in a partner when it comes to sexual compatibility?”
  • “What is your opinion on open relationships or non-monogamy?”
  • “Have you ever had a crush on someone who was unavailable or off-limits?”
  • “What do you think makes a sexual relationship satisfying?”
  • “How do you express your sexual boundaries to a new partner?”
  • “What is the sexiest compliment you’ve ever received?”
  • “In what ways do you like to express physical affection?”
  • “What do you think makes a good lover?”
  • “Do you feel comfortable trying new things in the bedroom?”
  • “What’s your opinion on porn and do you watch any yourself?”
  • “What’s your opinion on sexting or sending sexy photos?”
  • “What has been the most interesting conversation you’ve had about sex?”
  • “If you could pick one thing that makes you feel sexy, what would it be?”
  • “How do your past sexual experiences influence your current desires?”
  • “Do you like to lead or follow in the bedroom?”
  • “Have you ever had a purely physical relationship with someone?”

Heavy

  • “What’s your most awkward or embarrassing sexual experience?”
  • “Where’s the craziest place you’ve had sex?”
  • “How long do you think you could go without sex?”
  • “What’s something that secretly turns you on?”
  • “What’s the hottest thing a guy can do during sex?”
  • “What’s your favorite position?”
  • “What’s one thing you’ve always wanted to do in bed with a guy but haven’t?”
  • “Have you ever had a one-night stand?”
  • “Have you ever had a romantic or sexual experience with another woman?”
  • “Have you ever had a sexual fantasy you haven’t shared with anyone else?”
  • “Are there any roleplay scenarios that you find particularly appealing?”
  • “If you could pick one thing to bring into the bedroom, what would it be?”
  • “Have you ever been caught in the moment and, if so, what happened?”
  • “Do any certain parts of the body make you aroused?”
  • “Have you ever hooked up with more than one person at once?”
  • “If you could describe your perfect sexual encounter, what would it be like?”
  • “If you could experiment one night with no strings attached, what would you explore?”
  • “What’s the most daring thing you have ever done in the bedroom?”
  • “What would you do if you could have an intimate weekend with someone you like?”
  • “What do you think is the funniest thing you have ever done in the bedroom?”
  • “What type of dirty talk do you like?”
  • “If you could give your partner one wild night of pleasure, what would it include?”
  • “What kind of foreplay do you find the most stimulating?”
  • “Do you have any guilty pleasure fantasies that you’d like to explore?”

Helping Her Overcome Sexual Shame

Remember that these subjects often trigger feelings of shame and defensiveness.

Sometimes, you will be met with hesitation and surprise when asking a woman a more intimate question. She may challenge you and put you on the spot about why you’re asking about this sensitive subject.

The absolute worst things you can do are apologize or try to explain why you didn’t mean to be “weird”. All you’re going to do is reinforce that this subject is shameful and wrong.

Instead, you want her to feel this is something natural, normal, and FUN to talk about. You do that by responding with confidence, positivity, and even playfulness.

“Shame dies when stories are told in safe places.” – Ann Voskamp

Here are 3 ways to make a woman feel more comfortable if she’s hesitating to answer a sexual question.

Own your question 

You ask, “Do you consider yourself a sexual person?” She responds, “Did you really just ask that?”

You can say, “Of course I did…(smirk)”. Or maybe she says, “Why are you asking that?” You can say, “Because I think a strong sense of sexuality is healthy. Also, it’s fun to talk about.”

Encourage her to open up 

You ask, “How important is a passionate sexual connection to you in a relationship?” She responds, “Why do you want to know?”

You can say, “I’m genuinely interested because it’s important to me. Promise I won’t judge.” Or if she hesitates, you can say, “No pressure, I’m just excited to learn more about you.”

Encourage her by opening up first 

You ask, “What do you find most attractive about a man?” If she seems nervous, you can say, “Personally, I find ambition in a woman to be a really sexy quality.”

Or you ask, “What was your first kiss like?” She responds, “Wouldn’t you like to know?”

You can say, “Yes, yes I would. Mine was horrible…I remember being so nervous that when I first went in to kiss her, I shoulder-checked her instead. I’d like to think I’m a lot better now.”

If you handle her hesitance well, she will usually open up about her sexuality. 

If you tried one of the above examples and she’s still uncomfortable answering your question, then I wouldn’t broach the subject further during this interaction.

When To Stop And When To Keep Going

Once you’ve gotten into an intimate conversation, you can progressively mix in heavier sexual questions with non-sexual questions.

It’s often nice to take a break from being flirty. It allows for anticipation to build and for her to want to get back to feeling romantic with you.

Just pay attention to how open and excited she is to share this side of herself. 

If she’s really into it, you can keep the conversation hot. It will often quickly escalate to getting physical. 

If she’s answering but not overtly passionate, you can take a break from those types of questions for the night. You don’t have to talk only about sex.

A couple of questions are often all you need to turn things from friendly to romantic.

You aren’t going to magically fall into bed with a woman. You need to bring your conversations toward more intimate topics as an interaction progresses. That’s how she’s going to get turned on and see you as a sexual prospect.

Finally, if you’ve been talking about sex with a girl, she’s probably ready to be kissed. Seize that opportunity!

Key Takeaways

  • On a date, dive into conversations beyond friendly topics to establish deeper connections.
  • Asking more sex-oriented questions can help uncover mutual interests in romance, attraction, flirting, and sexuality.
  • Don’t shy away from expressing your sexual interest. Make the topic of sex fun and no big deal. This creates a comfortable atmosphere for women to embrace their sexuality.
  • To help women think about sex with you, show that sexual conversations are not shameful, but a healthy part of building a romantic connection.
  • Don’t wait for a “perfect moment” to talk about intimate topics. After about 15-30 minutes of conversation, you can smoothly segue into more personal questions.
  • Questions to explore can range from light, such as “What qualities make a man instantly attractive to you?” to heavier ones like “What’s something that secretly turns you on?” depending on how comfortable she seems.
  • If met with hesitation, don’t apologize. Respond confidently and encourage her to open up.
  • You can progressively mix in heavier sexual questions with non-sexual questions as the conversation goes on. Pay attention to her openness and excitement, and adjust the conversation pace accordingly.
  • Turning friendly conversations into romantic ones requires intention and progression. If you’ve been discussing sexual topics, she’s likely ready for you to make a move.

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