What to Know before Having Sex with a New Man: 3 Questions to Ask Yourself


If you are single, chances are you may be struggling with this question.  If you have single friends, you probably hear about it a lot. And I hear about it frequently in my private practice.

This question is so frequently asked because this is easily one of the most complicated modern dating dilemmas, especially for women.

What’s the question?

When is the right time to have sex with a man for the first time?

In the old days, women were supposed to wait until marriage to have sex.

All those rules were thrown out the window a long time ago, but we didn’t replace them with anything except the toxic three-date-rule.

You probably have heard of the three-date rule – if you go on a third date, it’s time to decide whether you will have sex with him.  Should that be the guideline?  It was not long ago that women were told to wait until marriage.

Match has reported that their Singles in America survey shows that 83% of singles prefer emotional maturity over physical attractiveness, and they have declared, “The hookup culture is history.” But they also tell us that about 66% of singles want to wait until after the 3rd date to have sex. And 27% want to have casual sex or friends with benefits.

This may seem like progress, but if we are still using 3 dates as any marker of when to have sex, that still represents a great deal of pressure for a woman. Why make such a major decision to be sexually intimate when you barely know the man?

We have a love-hate relationship with rules. We resent having to follow them and want to break them, but they give us a structure that can be comforting. They can guide us whether we like it or not.

The real problem for women is when they let cultural pressure dictate their behavior. Only you can know if you are truly comfortable and what is best for you. When you prioritize cultural norms over your instincts and intuition, you simply aren’t being true to yourself. This is the kind of decision that requires both careful deliberation and a little soul-searching.

You don’t want to think, “We’ll probably do it eventually anyway, so what’s the big deal?” That thought process just avoids decision-making.

Here’s the secret:  blindly following rules won’t lead to happiness.  After 30+ years of helping women get what they want from men, I can tell you that the answer lies in being your own Brand of Sexy.  That means you discover what is best for you and act accordingly.

Sex is about much more than the physical act.  For most women, sex opens you up to a whole new level of intimacy, connection and vulnerability.

But this decision does not have to be overwhelming or scary.  Here’s what to do before having sex. Answer these three questions and you will know when it’s right to sleep with him for the first time.

1-  Does he want what I want?

Before you have sex with someone new, you want to know him well enough to know if you have the same goals for the relationship.  Do you both want something serious?  Or is one or both of you looking for a casual fling?

These are questions to ask a guy before sleeping with him. Perhaps you feel awkward talking about what to know before having sex.  If you don’t feel you can talk about it, you may not be ready to have sex.  You want to get the answers you need so you are not sorry later.

2-  How will I feel if we have sex, and he disappears?

This question may sound negative, but it’s realistic and important.  There are questions to ask yourself about your relationship. Ask yourself – can you handle your feelings if you are physically intimate and never hear from him again?  Or if you continue to hear from him, he just wants “booty calls” and no longer wants to take you out on a date. He just wants a hookup.

Society may tell you that you should be able to just brush the feelings aside and move on.  You are a modern woman, after all!  Some women may be able to do that.  I’ve found that most cannot.  Be honest with yourself, protect your heart, and uphold your standards.

3-  How much will I regret passing on sex if I never hear from him again because I passed?

This is a very common fear. Women know that every man has his limits and many fear that he will bolt if she is not ready for sex when he is.

Here’s the follow-up question:  If you think you need to have sex to keep a relationship, is it really a relationship you want?  Only you know the answer.

An important fact you should keep in mind is that a man who is really into you will wait a lot longer than 3 dates to have sex. A keeper wants to make you happy so he will want to wait until you are comfortable. That will be much more important to him than the number of dates you’ve had.

He might want a little reassurance that you find him attractive. He may ask if you are saving yourself for a committed relationship or marriage. He may just want to know where he stands.

Bottom line:

Once you get clear on your answers to these three questions, you will save yourself worry, stress and regret. You will have sex when it’s right for you – and you will be setting yourself up to take a beautiful next step in your relationship.

Have you ever asked yourself these questions?  Do you wish you had?  How would your decisions have changed?  How do you plan to use them in the future?   I’d love to hear from you.  Please let me know in the comments below.

You can do this.  Be your own Brand of Sexy and get what you want.

Share This:

Leave A Reply

Your email address will not be published. Required fields are marked *