How to Have Sexual Conversations with Women

Clark Gable Flirting

“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.

They stared back in disbelief and laughed nervously. One of the girls 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?

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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 sexuality.

Deep down though, 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.

Fly into the Danger Zone

Archer Danger Zone

So how do you approach the topic of sex tastefully? Well, let me get this out of the way first…

Stop waiting for permission to move into intimate topics. Very few women are going to lead it there or say “You can ask me about sex now!”

Now if you’re naturally discussing a related topic like The 50 Shades of Grey movie, past relationships / hookups / dates, online dating, or first kisses — then take that opportunity to move into more intimate topics. But you can’t always rely on getting “gimmes” like that.

There isn’t a perfect moment or time. You have to take a chance and lead into these sexual subjects.

Instead, assume if you’ve been talking to a woman for a minimum of 15-30 minutes (at a bar or on a date), it’s safe to try leading into more enticing conversation.

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

From there, you can immediately roll into your sexual question to open up a discussion.

Getting to the good stuff

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.

Instead, start with lighter questions. If she’s discussing them with you, you can move towards heavier ones.

(Examples go from lighter to heavier)

  • “What do you find most attractive about a man?”
  • “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?”
  • “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?”
  • “Where’s the craziest place you’ve ever had sex?”
  • “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?”
  • “What’s something that secretly turns you on?”

Helping her overcome that 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.

Here are 3 ways 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.

Once you’ve gotten into an intimate conversation, you can progressively mix in heavier sexual questions with non-sexual questions. You don’t have to talk about sex endlessly unless she seems really excited to. A couple of questions is 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!

If flirting remains a challenge for you, I don’t want you to feel like you have to do this alone. If you’d like a step-by-step, tailored approach to consistently escalate your relationships from friendly to flirty, let’s have a free, 100% confidential consultation call (up to 30 minutes) to discuss how we can work together.  Schedule your free strategy session here.