by Felicity Keith
I’ve been asked to a bar by my friend Jessie. She wants me to meet this new guy she’s been dating for a couple weeks. Wants to get the “friend opinion”. The night is going well, he’s a great guy and I think they have a shot at this. He excuses himself to go to the bathroom and it gets quiet between us. “He seems great Jessie, I think you should keep dating him”. She giggles and swirls her cocktail. “What is it?” “Look, I know you’re my friend but I also know you’re in the business of love and romance…” Oh god. Here it comes… “When should I sleep with him?”. I use all available energy to not bang my head into our table in frustration. I look her in the eyes “Whenever you think it’s right”. She sighs, audibly acknowledging that that wasn’t the answer she was looking for.
Every woman I have ever known, and the thousands of women who write me emails have the same question:
When Do I Sleep with Him?
And I get it. Because when that question comes up 100 different things run through your head:
- If I sleep with him on the first date am I too easy?
- If I wait a week will he think I’m a prude?
- What if I’m ready but he’s not ready?
- Does he just want sex or does he want a relationship?
And 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. And 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 and how to turn that first date kiss into a steamy night without ever taking off your clothes.
So let’s dive in!
The First Date Sex Myth
Over and over again women are told that if you sleep with a man on the first date you’re too easy. Well, I call BS. For some couples, sex on the first date is exactly what they both want and need and they go on to have fantastic relationships. For others, waiting is what is better.
But before we jump into that, let’s talk about the actual date itself.
A date is longer than one cocktail, one coffee, one movie etc. A date is when the two of you spending actual time talking and getting to know each other. If you get together, have one cocktail, and 30 minutes later you’re in his bedroom ripping off each others clothes off, you’re hooking up.
I’m not considering a movie a real first date because you two don’t talk to each other. You sit in silence for 2 hours watching something and then because of the emotions of the movie etc you might end up hooking up.
On a first date you either feel a connection or you don’t. If you don’t, well you’re probably not having sex, unless you are both just physically attracted to each other and you both want to hook up.
If you do feel a connection, then sex is always on the table. In fact, I can guarantee you that if the date is going well he’s already undressed you in his mind and thought about the sexy noises you make when you are reaching climax (hell, you probably have done the same to him).
But should you sleep with him?
Bottom line, that is your choice, but here are some suggestions I have for you:
Always kiss on the first date. That kiss is going to tell you everything. You should have read my How to Kiss a Man and Make Him Love You program and know all about the chemistry of the kiss and how to drive him crazy with those lips of yours.
Here is what I recommend. Kiss him and 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? If the answer is yes, ask yourself, do I want to sleep with him tonight? Or do I want to leave him dreaming about me all night and all day tomorrow because that kiss was so electric.
A good tease, is a good tease, and everyone likes it.
I’m going to go on record and say that you shouldn’t sleep with him on the first date. Give him the best kiss he’s ever had, 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 and down the street like he’s in an old musical professing his love 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 is right for you.
If you decide not to sleep with him on the first date, I would sleep with him on the second date (as long as the second date is just as good as the first).
The second date?! Felicity that’s too soon! How do I know if I like him?!
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 a couple weeks before sleeping with him”. There is a big danger in this. Waiting too long to sleep with him is a death sentence for the relationship. When I ask 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 and I moved on”. And then women are confused because he stops calling them and going on dates. So, waiting a date or two is fine but if you wait too long you’re going to send the wrong message.
I don’t want to sleep with him until we are in an exclusive relationship…(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.
The problem women who want to wait have is that they don’t communicate this with the man they are dating/seeing and then find out he’s been sleeping with other women and suddenly we have Pompeii 2 on our hands.
This is NOT 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.
What if he REALLY wants to come inside or have me over and I kind of want to?
If you’ve had a solid, real first date and want to have sex with him, do it. If you have had a great first date but don’t feel comfortable having sex but still want to mess around there are tons of other options for you.
Make out like teenagers
Blowjobs
Hand jobs
Teasing him with words
“Not tonight, but very, very soon”
“I really want to rip your clothes off but I have a big day tomorrow and I want to make sure we have the entire night to be with each other”
“Next time…”
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 and 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. He’s not worth your time.
How Do You Know if He Just Wants Sex
None of us want to feel “used” or “tricked”. There is nothing worse than thinking things are going well with a guy only to sleep with him and never hear from him again. Or worse, only hear from him when he wants to have sex.
“But Felicity, 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 and know that he isn’t just using me for sex?”
Ah, sounds like you’re making sure he’s the “right one”. Well, you aren’t going to know if he’s the right one for you until you have sex. As my brother always says “You test drive a car before you buy it”. Having sex allows you to know if there is something beyond the kiss, something beyond the lustful feelings you have. It let’s you know if there is something between you two, the magical thing we like to call a spark.
One reason women want to wait to have sex with a guy is because they want to make sure that he wants more than just sex. They don’t want this to be the first and only date. Unfortunately a lot of guys will do this. They will take you on that first date, get laid and then never contact you again. It’s another reason to wait until the second date to sleep with him. If you don’t sleep with him on the first date and never hear from him again? Well, he just wanted sex.
In person red flags:
He Doesn’t want to have a REAL date
His idea of a date is getting a drink and then he quickly wants to move elsewhere.
He wants you to “come over and 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 inappropriate questions about your sex life
If he is asking you 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, not your sex life.
After you have your kiss he’s TOO pushy about taking things further
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.
Texting red flags:
He wants a dirty picture
Do not send explicit photos to people you don’t actually know. And by the way, you don’t KNOW someone after a first date. You’ve started to get to know them, but you don’t actually know them. If he wants a dirty picture 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 and drop all contact.
If he wants to throw a fit or coerce you into sending a picture he just wants sex.
He only contacts you when he is horny/ “U up?”
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 and 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 and then go home…he’s going to do that as long as he possibly can.
Stop and think about why you like him. Do you like him just for the sex you had? Do you actually know him? What about him is attractive to you (and I don’t mean physically). Do you find that he has a sense of humor that attracts you? Do you find he is a family man and you are drawn to that? Do you see an actual future with him?
If you find legitimate reasons on why you are interested in him then actually you need to take sex off the table.
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. Texting him without having to mention sex.
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 dating or exclusively dating in a month, move on.
Once you do this, one of two things will happen. Either he will warm up to you and 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 and isn’t ready for a relationship.
And that’s okay.
He’s not ready for a relationship, or he doesn’t want one right now. You have to accept that and move on.
So there you have it. The answer to the age old question. When you sleep with a man is your business. But remember, waiting too long can ruin your chances with a guy. Being in a relationship or trying to start a relationship requires risks. You have to take the risk and 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 and want, you’re going to watch life pass you by.
Always stand up for yourself. Never sleep with a man until you are ready.
