When Do I Sleep with Him?

Because when that question comes up 100 different things run through your head:

If I sleep with him too soon will he think I am too easy?

If I wait TOO long, will he think I’m a prude or lose interest?

What if he’s clearly trying to…but I don’t feel ready?

Does he just want sex or does he want a real relationship?

I don’t want to mess this up!

& the list goes on and on and on…

What women want is the magical number. That magical number saying “Here, this, THIS is when you sleep with him”.

But it doesn’t exist. & it never will.

Why?

Because all relationships are different.

So if there is no magical number I can give you, why did I write this? Because, while there isn’t a magical number, there are some ground rules you can lay down to make sure you sleep with him when you want to.

We’ll also cover knowing if he just wants sex, or if he wants a relationship & how to turn that first kiss into steamy sexual tension without ever taking off your clothes.

So let’s dive in!

The First Date Sex Myth

Over & over again women are told that if you sleep with a man too soon – let’s just say the first date or two – you are too easy. Well, I call BS, but it depends on YOUR intentions. For some couples, sex on the first date is exactly what they both want & need & they go on to have fantastic relationships. For others, & I’d have to say, the majority of new relationships, waiting is better.

Before we jump to that, let’s talk about what I mean by a “date” in the first place.

A date is longer than one drink, one coffee, one movie (no one talks to each other during movies anyway, right?) No, a real date is when the two of you spending actual time talking & getting to know each other. If you get together, have one cocktail (or four), exchange a few witty pleasantries, & soon you’re in his bedroom ripping off each other’s clothes off, you’re clearly just “hooking up”.

That’s fine if that’s what you’re looking for…but if you were hoping for a deeper connection, you’ve just sunk that battleship.

Also, remember what I said earlier about how men are wired for the chase? (I said it a hundred times for a reason!) By sleeping with him, you are depriving him of the opportunity to try & earn you over time. To fantasize about what you look like naked, & to try & devise a plan to get you to want him too.

I can guarantee you that if the date is going well he’s already undressed you in his mind & thought about the sexy noises you make when you are reaching climax (hell, you may have done the same to him).

So, should you sleep with him?

Bottom line, that is your choice, but here are some suggestions I have for you:

Don’t Be Afraid to Kiss Him

While I’m saying you might want to slow your roll when it comes to a first-date naked tango lesson, I don’t feel that way about kissing.  Kissing is awesome.

First, that kiss is going to tell you a LOT about this guy’s potential. There’s some fascinating science of what kissing tells your brain about a potential partner. There’s a mini-chemistry course happening in your mouth (um…yay!?) when you swap saliva. Your pheromones & genetics do instant calculus to determine how compatible your DNA is & your brain quickly translates that into “yum, I could kiss this guy all night.” or “ick, this feels like kissing a friend.”

Plus, it clues you in about what he’d be like in bed. Is he respectful of your face or does he launch an all out tongue-assault on your mouth? He could be inexperienced, but a kiss is a conversation & he should be listening to your signals while he does it.

Lastly, & not at all leastly, a kiss will turn him on, sending his brain into a shaken snow-globe of pleasure chemicals. He will be primed for the possibility of more, & leaving him wanting at the end of a date is the perfect state of mind to get his competitive instincts humming.

Here is what I recommend. Kiss him & step back. How was it? Did you find a fire light up inside you? Do you want to kiss him again? Do you want to rip his clothes off? Do you want to leave him dreaming about me all night & all day tomorrow because that kiss was so electric?

A good tease, is a good tease, & everyone likes that.

Give him the best kiss he’s ever had, & leave it at that. Make him pull his phone out as he’s walking away from your door in a desperate need to text you. Make him want to run up & down the street like he’s in an old musical professing his love for you to the world.

I want to be clear, that if you WANT to sleep with him on the first date you are absolutely allowed to. That is your choice! Always do what feels right for you.

Waiting to Make Sure He’s the “One” First?

I hear women say all the time, “I want to make sure he’s the right one before I sleep with him” or “I don’t want to come off easy so I’ll wait as long as I can before sleeping with him”.

There is a danger in this. Waiting too long to sleep with him can be a death sentence for a new relationship. When I ask other men about this question the response is the same “She never wanted to have sex, so I figured she wasn’t actually interested in me & I moved on”. & then women are confused because he stops calling them & going on dates.

Only you will know when waiting has gone from “I want to be a ‘Dreamgirl’ so I’m not going to rush into things’ to just playing a game, trying to make him ‘earn sex’ by some arbitrary metric that even you aren’t sure about. So, waiting is fine but if you wait too long you’re going to send the wrong message.

If you have gone on multiple dates, & you sense his expectations of sex are really different than yours, you can always talk about it. You won’t sound like a nun if you do. When it comes up, you can just say, “Kissing you is awesome, I’m just trying to get to know you better before taking it further”. He’s not 18… he can handle it. & you aren’t a teenager either… you don’t need to feel pressured about this stuff.

What if I don’t want to sleep with him until we are exclusive…or married?

There are plenty of women who want to wait until they know the man isn’t sleeping with anyone else before they will go to bed with him. That is totally fine but you HAVE to let him know. That’s communicating your boundaries, & that makes you a strong confident woman.

The problem women who want to wait have is that they don’t communicate this to the man they are dating/seeing & then find out he’s been sleeping with other women & suddenly we have Pompeii 2 on our hands.

Don’t keep your beliefs on sex a secret!  If you want to wait, then you have to tell him. Most likely you’ll want to find someone who also shares your beliefs on the subject – & communicating it clearly is a great way to figure that out.

What If He REALLY Wants Me to Come In &… I Kind of Want to?

If you’ve got a solid, real connection brewing & you want to have some sexy time with him, do it. There are SO many options available if you aren’t into having intercourse yet – or taking on all the health risks that come with fooling around sexually.

Things you can do, in order of increasing safe-sex risk:

Make out like teenagers

Take a shower together by candlelight

Masturbate together (this is really fun to do in the pitch dark the first time)

Foreplay like hand-jobs or oral sex

Besides, you probably want to see what his house or apartment looks like anyway, right?

Other Ways to Keep a Sexual Spark Without Having Sex

Kissing is the all-time classic way to rev up the engines without full-blown sex but you amp it up even more by:

Teasing each other with provocative words/phrases like:“Not tonight…but soon…”“I really want to rip your clothes off, but I have [to work / plans] tomorrow & I want to have all night to be with each other”“Next time…”

Sending innuendo-laden texts about what you are fantasizing about.

If he is any kind of decent man, he will accept what you say. There might be a small push back, because he wants to rip your clothes off right now, but good men will accept it & be happy about it. If ANY guy pushes you too far or gets upset that you don’t want to have sex right then, don’t see him again. That’s a red flag. He’s not worth your time.

How Do I Know If He Just Wants Sex?

Nobody wants to feel “used” or “tricked”. There is nothing worse than thinking things are going well with a guy only to sleep with him & never hear from him again. Or worse, only hear from him when he wants to have sex.

“Um, but earlier you said that I shouldn’t wait too long to sleep with him. How do I sleep with him in a reasonable time frame & know that he isn’t just using me for sex?”

Ah, sounds like you’re making sure he’s the “right one” before you have sex. Sorry, some things are just unknowable (though see below for some hints…). You see, unfortunately, some men are entirely capable of pretending they want more from you than just sex, then surprising you by “ghosting” you after you’ve hooked up.

In all fairness, the guy HIMSELF might not have known what he wanted until he had sex with you – & it caused him to rethink what HE wanted. Or maybe you’ve changed your mind about HIM post-frolic too! Having sex allows you to know if there is something beyond the kiss, something beyond the lustful feelings you have.

Sometimes, having sex is part of the process of getting to know someone. It lets you know if there is something between you two, the magical thing we like to call a spark.

If you have sex, & he suddenly gets really sparse or far away, that tells you something very important… that he’s clearly not on the same page as you. He also isn’t respecting you & treating you the way you deserve. Consider the bullet dodged & move on.

Signals He’s Just Using You for Sex

If you’re looking for a casual hookup, that’s your absolute right as an adult. Don’t feel an ounce of shame about it! But if you are looking for more of a serious relationship, here’s a handy list of signals that a guy is just using you for sex:

He Doesn’t want to have a REAL date: His idea of a date is getting a drink & then he quickly wants to move elsewhere. He wants you to “come over & hang out”. A first date should be somewhere PUBLIC.

He constantly talks about his sex life: If he is spending a lot of time telling you about his sexual adventures or how good he is in bed, he just wants to sleep with you. This doesn’t mean these topics won’t come up but you don’t want it to be the main topic of conversation.

He asks graphic questions about your sex life: If he is asking for details about your previous partners, or the craziest place you’ve had sex, or your favorite position, he most likely just wants sex. He should be asking about YOU as a whole, not your sex life.

He’s pushy: After you have your kiss he’s TOO pushy about taking things further. Is he trying too hard to “negotiate” his way into your pants? No means no. If after that mind blowing kiss you give him he keeps pushing to come inside or for you to come inside, he just wants sex. Men who want more than sex will not only respect your wishes but will be excited that sex is on the table, just not tonight.

He wants a dirty picture. Don’t send explicit photos to people you don’t know well & completely trust. The internet is filled with harrowing tales of guys spreading around photos that woman sent to them in confidence.If he wants a dirty picture soon after you’ve started dating, just let him know that you don’t send pictures like that to people you have just met. If he throws a fit, tell him thanks but no thanks & drop all contact.

He only contacts you when he is horny: Beware the tell-tale 2:00AM “You up?” text (or it’s more millennial cousin, the “U up?” text) If it appears that every time he texts you, no matter what sweet things he says, he mentions getting together for sex or wanting a dirty picture or just talking about how much you turn him on, he just wants sex.

He Just Wants Sex, but I REALLY Like Him

Let’s make this clear:

Sleeping with a man will NOT make him fall in love with you.

Romantic comedies & romance novels are filled with this BS, but it’s not real life. If he can meet up with you, have no strings attached sex & then go home…he’s going to do that as long as he possibly can.

There is simply no way that you can MAKE a guy fall in love you, simply by your supernatural sexual prowess. You can get him to want to have sex with you a lot, but I assure you, men are more than capable of keeping that activity very separate in their minds from falling in love. In fact, they can have sex with woman they don’t even LIKE as long as they find them attractive on some level.

Let me be clear, this is not REFUSING TO HAVE SEX. This is making the relationship about MORE than sex. This is making sure you guys go on real dates that end with no sex. Establishing a real connection outside of the bedroom (or couch, or kitchen table…)

Now, women can easily get trapped in this situation because the guy can string you along for months. Give yourself a cut off. If you aren’t seriously (or exclusively) dating in a reasonable time frame (say 1-2 months), it’s time to move on with a polite, “thanks for the sex, but I’m looking for a different, deeper, sort of relationship.”

Once you do this, one of two things will happen. Either he will warm up to you & the idea of actually dating you or he’ll drop contact/throw a fit/let you know it’s over. If that happens, he just wanted sex & isn’t ready for a relationship.

& that’s okay.

He’s not ready for a relationship, or he doesn’t want one right now. You have to accept that & move on.

Always stand up for yourself. Never sleep with a man until you are ready

So there you have it. The answer to the age-old question. When you sleep with a man is your business. Doing it too soon or too late can make things complicated, but as long as you trust your gut & don’t do it until you feel comfortable, you’ll be fine.

Being in a relationship or trying to start a relationship requires risks. You have to take the risk & the jump to see what beautiful thing might grow. If you sit around waiting forever, trying to fill out some list of demands about what you expect & want, you’re going to watch life pass you by.