When Should You Sleep with Him? A Simple Way to See if You’re Ready to be Intimate

As a former matchmaker and today, as a dating coach, I get this question a lot.

To be truthful, this question is something I thought about a lot during my dating days. And something that I’ve talked about with girlfriends a lot.

The question in question?

When should I sleep with him?

I actually googled this question online just to see what would come up. And a lot came up.

So before I answer this question, I want you to know that every person and every situation is different. And no one knows what is best for you, except you.

However, you’re here for a reason. So, here are my thoughts.

My general rule of thumb is that if you two haven’t discussed where you stand in the relationship. And if you’re not clear and comfortable with where that conversation landed you, you shouldn’t sleep with him.

If you want a relationship, before getting intimate with someone, you want to know that that person isn’t sleeping with other people and is committed to fostering your relationship too. Basically, you want an exclusive, monogamous relationship.

You want this, so you can feel safe and clear-headed. And, so you don’t become panicked or full of anxiety that he (or she) isn’t going to stick around after the deed is done.

Think about it, if you two sleep together and you have no idea where you stand, how are you going to feel?

This is a great barometer to see how you actually would feel if you slept together without clearly discussing and defining the relationship.

What happens if you do become intimate without clearly defining the relationship?

Honestly, every single relationship and dating experience is different. But what I can tell you is that when women become intimate before being in a defined monogamous relationship, what typically ends up happening is she feels like she lost some of her power. Which makes her feel insecure. And because she feels insecure, she wants reassurance that things are still going well. And if the man isn’t giving her the reassurance that she needs, she becomes needy. And this neediness is a sure-fire way to make attraction fizzle out.

Lots of times women are afraid or don’t know how to bring up the topic of intimacy. Again, every experience and how things play out are going to be different, but what I recommend clients do is to bring it up, if things are getting a little hot and heavy, or if the topic naturally came up in conversation.

What you want to do is let your new dating partner know that you do find them attractive, but that you’re not ready to become intimate or sleep with them. And let them know where you stand on the matter.

For example, “I know we haven’t talked about sleeping together before, but I feel it’s the right time to bring it up. I am attracted to you, but I just don’t feel comfortable taking that next step until I’m with someone exclusively and we’re both on the same page.”

Then wait and see what your love interest says.

This statement is an excellent way to have the conversation then and there. Or, it’ll be something to come back to and discuss later. It’ll also be an excellent way to see if this person is in things for the right reason.

The right person will honor what you’re saying and wait, even if they don’t want to. And make it obvious to you that they are invested in the relationship and they want to move forward.

If they can’t make things clear for you, or they avoid this conversation, this is a sure-fire sign that this likely isn’t the person for you.

What’s also a sure-fire sign that they’re not right for you is if you don’t feel comfortable having this conversation with them. Trust me on this one. As graphic as this may be, if you’re literally going to allow someone to be inside of you, but you can’t talk to them about the act, they’re not for you.

If even thinking about talking to them about this is giving you anxiety, they don’t make you feel safe.

No matter how much you like them, if they aren’t willing to talk to you about your relationship, or intimacy. And they don’t make you feel safe and secure in the relationship, move on.

Because, my sweet friend, someone else will.



p.s. want more advice on dating? check out Single & Sane.