When Should a Woman Have Sex With a Man?


The end of Wednesday’s blog post brought up a very important topic; perhaps the most common question I get asked by women whenever I give a speech:

Turn sex into a reward for good behavior and time put-in and you’re missing the entire point.

How do you know when it’s okay to sleep with a guy?

I discussed this back in March, but most of you weren’t reading then. So forgive me for recycling, but my views haven’t changed, and you definitely want to get in on this discussion…

No doubt about it: The first time a woman beds down with a guy she’s crazy about is an exciting and special time. Still, the question remains: When? Well, it depends. Some women are happy to get down to business the night they meet; others will wait weeks or months before doing the deed. Whatever a woman’s decision, we had to wonder: Does the double standard still exist today? In other words, if a woman knocks boots with a guy too soon, does she automatically nix her chances for long-term love–or is that old-fashioned nonsense in today’s modern-day dating scene? To find out, we grilled three women about the ups and downs of when they get down to business… and what they said may surprise you.

My two cents on the whole thing?

Men are sexual hypocrites. They push women for sex, then blame them for having sex. They’re particularly stuck on the idea that if a woman hops into bed with them quickly then she must have done this with lots of other men as well. This lowers her value in his eyes. After all, if everyone can have her, she can’t be all that special, can she?

On the other hand, I also know from personal experience that if a guy is crazy about a girl, and they move really fast, all the rules go out the window. In fact, this is the way MOST of my relationships have started. But then, I’ve always been determined not to be hypocritical when a woman has the same lack of morals I do. I love women with loose morals.

Men are sexual hypocrites. They push women for sex, then blame them for having sex.

The sex question is a popular one because it comes up in every dating situation. However, there’s no set timetable or finite number of dates that will let you know when it’s time to give it up. I know one woman who was told by an “expert” to wait 10 dates before sleeping with the man she was dating. The guy dumped her her after 7. … That’s what you get for playing by a made-up set of rules. Sex isn’t something you “allow” him to do. It’s something that you share and create together. Turn sex into a reward for good behavior and time put-in and you’re missing the entire point.

As a woman, your job is not to come up with an arbitrary number of dates, like the U.S. coming up with a pull out date for our soldiers in Iraq. Your sole responsibility before having sex is to figure out if he’s interested in YOU or in SEX.

I repeat: Your sole responsibility before having sex is to figure out if he’s interested in YOU or in SEX.

If you don’t know the answer, don’t have sex. If you think you know the answer, then have sex. And if you can’t handle the emotional consequences of making an occasional mistake, you probably shouldn’t sleep with anyone until you’re in a committed relationship.

This has been my personal policy for the past three years – no committed relationship, no sex – and it’s worked very well for me.

What are YOUR thoughts? Men, I want to hear from you, as well…

Join our conversation (320 Comments).
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  1. 221

    As if you can tell a man’s intentions when you go on one lousy date!! lmao…I love how you’re not supposed to talk about certain things on a first date (exes, politics, etc.) but it’s okay to do the most intimate act (have sex)?!?! Wtf is wrong with this world?!

    Plain and simple, if you’re a slut go for it! Common sense tells me if you’re looking for a relationship, don’t do it (this is a no-Brainer duhhhhh)

    It’s sad because I feel like all the dumb sluts out there (and nowadays their everywhere thanks to articles like these) make it more difficult for women looking for relationships to get into relationships   (at times)

    1. 221.1

      Jenny, agreed. If someone likes sex and especially having sex with different partners, they should just embrace it. If someone dreams on waiting until marriage, they should tell their dating partner and wait and see. I miss honest talking that matters a lot these days. I don’t care if someone likes the same music or movies like me but people do not discuss the most important things or lie about it even to themselves. I know a girl who loves having sex but her promiscuity cost her her one relationship which she claimed she wanted. If you want a stable relationship, you should show that you are a stable with your choices first, if you have no idea, I would recommend waiting and not giving in peer pressure or media representation – what feels wrong is wrong and what feels right is right to you and you only, if you want to have lots of sex with different guys/girls, go for it but let the person you date know it.

  2. 222

    In my personal experience, it been women that instigate and have pushed me for sex. I will be dating a women and eventually sex talk of some for occurs. For my life I’d say it’s been initiated by the woman almost 100% of the time. I don’t necessarily mean talking about having sex with me – just in a general way relating to them. Some examples of things I’ve heard:

    I haven’t had sex since my divorce.

    My ex could keep up with my sex drive

    What I look for in a man is x,y and great sex

    I hope you don’t think that you are getting any tonight

    I don’t need a man, I’ve got my toy

    The women that said these things to me did what I guess I’ll call a soft push. It’s enough to get sex, but not so much as to where you will mentally claim to be the person instigating the sex (you can get the man, but still have plausible deniability if you choose). I will admit that I am not that hard to get and don’t necessarily require much pushing!

    A  woman once asked me if I remembered when her and I had first had sex. Our versions of the tale were very different.

    Her version – We went out to the bar on a date, had a few drinks & shoot some pool. Afterwards we went back to your place, ate, drank some more, watched a movie, started making out, then had sex a few times through the night.

    Short and sweet. I asked her about the detail, but she couldn’t remember.

    My version – We didn’t go out on a date. You got my phone number from your bestie, whom you knew I was having a fwb relationship with at the time. You wanted to know if the three of us could all go out to have a few drinks. My fwb declined because she was busy, but I was game for a drink (it was college – I was always down for a drink). I met you downtown way before dark and we drank, played pool and chatted. I was tired of spending money at the bar and I was also hungry, so I suggested we got to the liquor store and head back to my place, since you didn’t live in town. We drank the liquor, ate, and watched  a bootleg of Forgetting Sarah Marshall. I remember because it cut out about a third of the way through and the bootleger just typed in what was happening. I was pretty irate about it. You didn’t want to drive home because you said you were too drunk. I told you that you could sleep on the bed and I’d lay on the floor. You said we were both adult and there was no reason we couldn’t just share a bed and sleep. Made sense to me – I don’t really like sleeping on the floor anyway. So there we were, both in the bed. SOMEONE started doing a lot of hip gyrating, claiming that she couldn’t get comfortable. Shortly after, that same person reached around and grabbed my crotch saying that she wanted to feel what was poking her. We had sex several times. You were distraught in the morning because you felt like you’d betrayed your best friend by sleeping with me. So distraught that you came back over after you got off work…..

    I would say that she was the one pushing for sex.

    One of my exes that I was with for 5 years did almost the exact same thing the first time we had sex. Except we were at her house. and She insisted that I was too drunk to leave and needed to stay. She also remembered me being the sexual instigator.

    A woman I had briefly been seeing invited me over. She liked that I was interested in getting to know here despite her making it immediately and repeated clear that she would not be having sex with anyone. She dropped the remote in my crotch while trying to change the channel and touched my manhood a bit trying to recover it – for which she apologized profusely. After doing it THREE MORE TIMES, she admitted that she wanted me to whip it out.

    A woman I went to have dinner with thought that it was nice to meet a guy that didn’t immediately bring up sex or try to send her dick picks. But I guess not seeing those dick pics and talking about sex made her curious, because she was asking if she could take an up close look at the goods  after dinner.

    I was watching a movie with a woman and she just randomly says “I hope you don’t think that we are going to have sex just because you are here and its late.” I said “You are the only one talking about having sex with anyone.” I thought that was that. Until a few hours later when she says “If you want, I suppose we could have sex. I mean it has been a while for me.”

    This one is my favorite: I was talking to a women I met an a dating site. We’d been on 1 date and had talked on the phone several times. I get a call from her basically saying that it isn’t going to work out between us because my dick is too small. Having never had any sexual conversations or sent her any pictures of ANYTHING, I asked how she came to this conclusion. According to her, if I were hung I would talk about it all the time and would have been trying to get her to look at pictures of it. I just started laughing uncontrollably. eventually she cussed me out and hung up. She texted me about a week later acting like none of that had ever happened. Soon after she asked for a dick pic. I declined. She send my naked pics of here and asked if I wanted to come over. I said no. She sent me a pic of her blowing some guy and said that it could be me. I said I was good. She got upset and said there must be something wrong with me for turning down a good woman that was throwing the pussy at me and told me to lose her number.

    I had a female friend that wanted to have sex with me, but she was in a relationship. She was very conflicted. She wanted sex with me, but didn’t want to cheat. She told me that she decided that it wouldn’t be cheating if we had sex because the condom would prevent my penis from actually touching her.

    Different female friend, same scenario – has boyfriend, wants sex with me. She calls me to come over so we can talk. She tells me that she doesn’t want to cheat on her boyfriend. She loves him. They have a good thing going. So her and I can’t have sex…………….But what is sex exactly? It’s vaginal intercourse. I was confused a bit, so I ask her to clarify. She says that we can’t have sex by her definition (vaginal intercourse) but anything other than that would be OK since it wouldn’t technically be cheating.

    Different female. Similar scenario to the previous two. My old neighbor. Lived with her husband and two kids a couple of houses down from me. People on the block were pretty friendly so we’d have neighborhood cookouts or a just have a few drinks and chat. Her and I had chatted several times, mostly about her and her kids. She was young, got pregnant and decided to get married. One day the regular conversation shifts to things she doesn’t like about her husband. I tell her that I’m sorry, as I could relate to some of her frustrations. But then she started talking about her sexual frustrations. That weekend, she asked if I could move their new washer and dryer and hook them up. I asked why her husband couldn’t do this and she said that she’d asked him to do it earlier in the week and he still hadn’t, plus he was at work at the moment. and she really needed to do laundry for the kids before they woke up from their naps. I agree to move the machine and hook them up. Didn’t take long. She thanked me with a kiss, some more kissing and some groping. Then she said hold on, “I don’t want to cheat on my husband. That would be wrong. But if we just do oral, that’s not cheating. Are you ok with that?”

  3. 223

    Well I’m still confused!! I met a guy went on a date a few days ago, he asked me out on another one so we’re going out next week. Weve got lots in common, even daft things, I’m really physical so is he. I do NOT want to be slutty and sleep with him too soon but I also don’t want to be over thinking and putting times, dates and limits on things that may take away the natural spontaneity of it all. It really sucks the double standards thing, men do not have these inner battles. To find out whether not he’s interested in you or just sex is a really great idea but I think men are always interested in sex even if they really like you too! And that goes for me too, you need the physical attraction/chemistry and to feel like you’d love to jump into bed with them which is obvious when you’re communicating! I know that if I sleep with him and get ditched days later I’ll be annoyed with myself but the only way to avoid that potential let down is just not to let go and do it in the first place. See? Confused!!!!! 😄

  4. 224

    If a guy is crazy about me, it won’t particularly matter when I have sex with him (ie it has just as much of a chance of turning into a relationship). This has also been my experience as a woman. So my conclusion from this is that it really doesn’t matter. If I genuinely like someone and feel a real connection I’m happy to have sex early on, probably not first date but second date onwards is good, depending on the vibe. If after that he loses interest I know he was never likely to be crazy about me anyway – I haven’t lost anything. So this is my policy going forward. Of course it helps that although I will only have sex with someone I like, I’m not going to be emotionally devastated just because we slept together. I’ll be disappointed because I liked them not because of the sex.

    I appreciate this article because it’s made me feel less angsty about when to have sex and whether someone will judge me for it as I genuinely wouldn’t want a relationship with a guy like that anyway.

  5. 225

    Men should be careful and not be a source of money for women. Some women claimed they want large sums of money before sex. This way they know the man is for them. But there are a lot of gold diggers. We all have to be careful.

  6. 226

    I am dating a guy from Canada and we have been communicating for almost 9 months   now. We’ve met   twice already and I can say that we both like each other. The thought of giving myself and having sex with him   wasn’t really that difficult because I like him   and I am strongly   attracted to him ( he is too with me).We almost did it,but in the process I begin to realized I wasn’t ready for it. He was probably upset, but he said that he wouldnt do anything unless I’m comfortable with it. I say,   any man   who does say that shows RESPECT for his girl.at least in my point of view . Any man who pushes you and gets upset for not having sex with him   is probably a red flag. So, I say learn to say NO if you really want to do find out if his into you or just want to have sex with you .This two letter word might just save a whole lot of trouble. There is probably no right time table when you have   sex with someone, but if your ready,it will happen naturally. I’d like to think that if it happens to me,   I should wake up and realized that I   don’t   have any regrets that   I shared the most intimate moments with him regardless if it happen   in   first date or   the   nth date.

  7. 227

    I just started dating a guy that is 56 I’m 51.   The girls I talk to are saying 2 months.   I have been around this guy for about 7 months but just started dating.   I think the next date it will be time 🙂

  8. 228

    Well there was this girl one time I met her, she was having a problem, but caused by the lack of brains she had, guess we both messed up to some point tho, but it was just 1 of those things we met off guard, but to me she was worth it.

    Anyway I left her stay over night and it was not long and we did it alright, sad part of it all is was she was the best I ever had, (a memory indeed!) and some 16 years later not only did she forget to cum back for I couldn’t find her again either, so we both lost.

    But due to reasons her head was sort of messed up for she couldn’t remember things like that vary long, so nevertheless being I still have no 1, she always been something to help me go to sleep on. but now I got 1, but so far away is she, the one above just might have to keep putting me to sleep night after night, but then also a memory from girls I went to school with long ago still cum to mind OH how I wished I cold of plugged them up so long ago, but now I wouldn’t even lick them any more no matter how good they ever were, so if it was not for the 1 above, I may not even have a memory, not sure I ever got her last name, but her 1st name she told me was Victoria, and yes I know, shit happens, maybe to me more than others, wish I could by all means run into her again like we did before by accident, but doubt I ever will now OH how sad……….


  9. 229

    Forgot to mention in my blog when I told you about a girl named Victoria,

    But anyway this is about those I remember from my old school days, ya there was two for sure I wanted badly, but the best part of it all as they were twins, and for some reason I loved there names,

    Not sure who cum out 1st but anyway there names were Eileen & Elaine,

    Elaine was a lot like Victoria in body, but Eileen was build like a brick s**thouse, and she was the who back in 7th grade I like her so much I almost wished (but didn’t) I’d a raped her, but now its an old dream, and its nice to still be a free man, but for some reason those two girls from back then still ring a bell in my head, for maybe it was just because of there names, anyway they never knew how badly I’d a loved having babies with 2 being twins and all…….

  10. 230

    Urrrmmm I think it’s pretty important to figure out if YOU LIKE HIM and want to HAVE SEX WITH HIM… these things are always putting the guy’said perspective first

  11. 231


    My wife passed way and   so I   was   forced to   go on line to find dates.

    I   have had sex on many first dates.     There were a few that I   dated several times with no sex


    The one   that I now love is   just what   I   want and need —We had great sex on the first meeting

    the night before      and the day after.


    It is my experience that   sex on the first date is no   big deal   if there is an attraction



  12. 232

    I’m dating again it’s only been just a lil over a month after being divorced since 2006, and   I don’t feel ready for sex. This guy is a nice fella and he’s pushing it I get right uncomfortable.   I have said, “If I am worth it, he should wait. ”   He says,” You are worth it”.   Then I sit pondering why push it?   If   man wants a women and she’s not ready to pursue a deeper thing like SEX, he should respect her.   It helps build a friendship in the relationship to a stronger bond, to see if he can live without her.     A relationship isn’t juut about sex it’s about a soulmate.   I used to be young and foolish, married and divorced.   I told myself this time do it right if there is such thing as MAKING IT RIGHT.   I want to be happy and deal with NO sexual pressures til I feel ready.   I guess I have been sexually assaulted in the past,   it’s hard trying to make my date UNDERSTAND that.

    1. 232.1
      Yet Another Guy


      A relationship isn’t juut about sex it’s about a soulmate.

      You do know that a “soulmate” is just a fantasy.   There is no such thing as a soulmate.   There are plenty of people for whom chemistry and compatibility exist, but the concept of a soulmate is just a Disney fairy tale that is sold to women when they are young, just like having a prince sweep a woman off of her feet.

      1. 232.1.1

        Its a fantasy rooted in the medieval European ideal of Courtly Love, where a Knight will do anything for his Lady, without any thought of recompense, and where sex is considered an impure distraction.

        But “I want to be happy and deal with NO sexual pressures til I feel ready”, how would that work? I think Kris was hoping for a strong, masculine man with such a highly evolved intuition he will just know when she is ready. In truth, she is more likely to find a shy, passive man who will always leave initiation up to her.

  13. 233

    I liked the column overall. I would say that men being sexual hypocrites is a bit of a sweeping generalization. Id say whatever you’re comfortable with. I was married for 13 years to a woman who I slept with on the first date. We were both comfortable with that. We’re divorced now, and I have started dating again. I can say that now, if I don’t feel like she’s entertaining the idea of having sex after 4-6 dates, I take that to mean that her interest in me is relatively low. I don’t pressure a woman to have sex with me, but I definitely communicate to her that the physical part of a relationship is important to me, including (but not limited to) sex. If she doesn’t kiss, hug, cuddle, or hold hands with me enough that means two things to me. One, it’s not as important to her as it is to me. Two, our relationship will probably not progress to the next level. Both of those things usually indicate to me that we probably aren’t compatible.

  14. 234

    yeah…sure. Ladies there are only 3 types of men in the world:

    1. the nice, successful, awesome men that want a relationship AND prioritize sex. (these are more “alpha” style men)

    2. the nice, successful, awesome men that want a relationship, and are WILLING TO wait for sex (these are more “beta” style men)

    3. losers.

    Pick your poison. you have a 33.3% chance at the man of your dreams. go get em.

  15. 235

    Wait until marriage to have sex if you’re a virgin. There’s plenty to do before jumping to bed to know the person – going for walks, attending events, meeting one’s family, camping, working on some charity or volunteering together, etc etc but the most important – is being honest with yourself and each other, tell them that you want to wait. If you don’t, then it’s up to the moment when it really feels the right time, no doubts, no second guesses, no peer pressure, no coaxing. If you have a thinnest doubts, listen to your inner gut – losing the virginity can be the most blessed or cursed moment of your life. IF you’re no longer virgin then I agree with Evan’s advice – Your sole responsibility before having sex is to figure out if he’s interested in YOU or in SEX.

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