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He Asks: “How Many Men Have You Slept With?” Here’s What You Say…

It’s almost inevitable you’re going to get asked…

When you do, how do you answer?

Do you need to talk about it or can the topic be avoided?

In this week’s video I share my philosophy on the question, and how you can answer in a high-value way.

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106 Replies to “He Asks: “How Many Men Have You Slept With?” Here’s What You Say…”

  • I usually answer with a line from the movie “Four weddings and a funeral”: “More than Lady Di, less than Madonna.”

  • My answer: Wow, that’s a really inappropriate question.

    I’m not interested in dancing around an answer. I’ll make it clear right upfront that this question is uncalled for. Personally, I see it as a sign or immaturity and shallowness, and if he pushes the question anymore, it certainly will be the end of the relationship.

    Just to make sure you are clear on this, a partner can contract “an itch” from having sex one time just the same as having sex 100 times. This answer does not in any case indicate the likelihood STD. Even if someone is a vergin, STDs can be passed from oral sex if a person has had a cold sore. I realize your song was just a joke, but in your position you have a greater responsibility to not carry forward misconceptions on such a serious issue.

  • And how about if I find that question interesting? I mean, I like to know the sexual past of the people who I´m with not to be jelous but because I want to know what is sexy to him or wich experencies he liked the most. And I want him to know the same about me. How about if I want a guy to like me with everything? With my sexual past and my stories. What do you think about it?

  • Matthew, what would you do in the situation where they ask and i haven’t slept with anyone before because im saving myself for marriage. I feel as though you cant really avoid the answer because there comes a point in relationships where he may want more. What would i say then without scaring him?

    1. I too would like to know that. Even if it is for non-religious reasons. Matthew, what would your answer be for the virgins, whatever their reason might be? When you reach a certains point in a relationship it is definetely a relevant topic and shouldn’t be put aside. If you are not honest with the guy it will get very awkward, because he is bound to find out at some point.

      1. I was thinking the same thing while watching the video. I’m a virgin, but it’s not for religious reasons.

        I’m in university and a lot of the relationships I see are short term and based off of the person they are having sex with for that month. Which is fine. Everyone feels differently about this and I’m completely accepting of it. But what I find hard is when I’m on a date with a guy and when they ask me this question, I can’t lie about me being a virgin. Especially, if it’s only like two dates in and they’re asking me this question. And when I’m honest with them, they get really turned off by it and I never see them again.

        I think about it and obviously if they are reacting this way, they aren’t someone who deserves me because they don’t respect my standards. But it’s very hard to be the girl in university who looks for the opposite of what everyone else is looking for during this time in their lives.

        Sex to me is not something that’s just “whatever.” I wouldn’t want to be doing it for just the pleasure of it and not caring about who I’m doing it with and being half drunk while doing it. It involves so much more than just the physical aspect of it. There has to be some sort of a connection. I would want to know of the character (I guess you could say) of the person that I would be sleeping with. And there’s a little bit of waiting involved with that. Not to say that it would be like a 6 months to a year wait, but you know what I mean?

        I would love to be intimate with someone in that way. It’s part of being in a relationship. But I feel like I’m stuck… am I crazy?!?! … lol

        I hope this makes sense.

        Thank you for your videos! :) Keep doing what you’re doing! I always learn something new from you! And I appreciate it tons! :)


        1. I so know what yall mean girls like it’s my fear of being in a relationship because sex is expected, eventually And society has made it seem its a bad thing jeez. Did yall see that girl from ready to love who was a virgin with Ben I just remember matt saying not to be scared to show sensual side

          I hope Matt or Stephen respond to this question

          1. I just don’t understand. Why does sex have to be the very first thing that two people do together when entering into a relationship? Like is that some sort validation thing for men? Like if they have sex with a woman on the first or third date or whatever and if the sex was good, then that gives them confidence (I guess you could say?) that the relationship can sustain for a longer duration?

            Because I thought it was the other way around. I thought it was having similar values that would sustain a relationship. I know sex is important too, but if that’s all there is, a relationship can’t last… that’s why it’s called sort term cause it’s based off of sex… lol

            To me, I find it attractive if I have similar values with someone. That makes me want to jump him… lol :P

            But then I try to explain this to guys and they think of me as crazy.


  • you made me laugh out loud, Matt :)))

    I have been through this question once and it did make me feel weird and…not at ease. This a very personal topic. It like letting somebody else entering the bedroom of your past.

  • Omg Matt you killed me with that little song you made up at the end for the fly. I’ve been asked before though by previous boyfriends and I decided to answer truthfully. I even asked those guys that question myself. It didn’t lead to anything good. Great advice, as usual. Thank you!!!

  • I think this advice is tailored more for people who have slept with more than five people. If you say two or three, I don’t think that will create the drama you mention in the video. I could be wrong, but most folks are fine with that, no further questions asked.

    I’m also surprised that you didn’t mention STDs. Although, anyone who is sexually active can get an STD, I believe it is more likely with numerous partners. If someone has had 15 or more partners, I want to know. Scientifically, condoms or no, there is a chance that what happened with one of those people will affect my health.

    I don’t judge any person on the amount of people they’ve slept with. Like other commenters, sometimes knowing calms things down since you’ve both shown trust and have become closer as a result of sharing. I think if the person does get jealous or overly fixated on this, then that’s a red flag you probably needed to know anyway.

    1. STDS is not a valid justification to asking that question. One can get an STD from their very first and only partner. If he’s slept with only three people will you think he’s “safer” than one who’s been with 10? Well maybe #3 guy was cheated on and got infected by a girlfriend while # 10 guy has always used a condom. A couple that is going into a more serious relationship should get tested. Number of previous sexual partners is not necessarily an indicator of someone’s character or safe sexual behaviour.

    2. And l can almost guarantee you that the guy asking the question is just insecure about his performance. He’s not thinking about STDs.

      1. I did say above, “Although, anyone who is sexually active can get an STD, I believe it is more likely with numerous partners.” So I acknowledge that one can get a STD with one’s first partner. I know of at least one person where that happened. But I do believe it’s more likely the more people you sleep with. Even with a condom. Less likely with a condom but still. There’s a chance just with having sex at all.

        My thing is I like to know what I’m getting myself into. I wouldn’t ask the question and no one has ever asked me. It’s kind of tactless and gauche a question. What I would hope is these things would come up and we’d volunteer the info. That has happened before organically in a conversation about sex. You don’t always even have to ask, honestly. If you’re around a person enough and really listen to him, you get all the answers you want without a single question.

        I still want to know. I don’t need details but I want to know if it’s 15 or more. As one says above, it says a lot about the person and how they feel about sex. Doesn’t mean I won’t be with them, just I want to feel they trust me and feel safe enough to open up with me. If they don’t, we probably shouldn’t be having sex in the first place. I’d never push the issue. Like many disclosures, I’d hope it would come out naturally as people build trust with one another.

        I could be naive, but I really believe this.

  • Wow Matt! You are so wrong! Of course you should know how many people your potential partner has slept with. And yes, the number of people you have slept with speaks directly to your character. If you have slept with a lot of people that means either you are a loose person( aka slut– eww, gross) or you suck at relationships. Why couldn’t you make any of those relationships work? Do you just quit at the first sign of struggle? Are you a cheater? Do you constantly date cheaters? If so, why are you such a poor judge of character? If you keep choosing the wrong people to be with, you have a problem. Are you a slow learner? “The past is the past” how many of your(not you personally Matt) exes have heard that line? The few decent people left in this world would like to know if they are getting into a relationship with a decent person or not. However, people can and do turn their lives around. Just be honest in all your relationships. Honesty is attractive. And if being honest is too painful then get your life together!

    1. Just because someone has had a high number of sex partners doesn’t make them an indecent person. I have slept with less men then most of my girlfriends (assuming they are telling the truth when we have girl chats) and yet I am far less conservative than they are when it comes to sex. The number of partners has no bearing on how good or bad someone is as a human being.

      1. Sure, sleeping with a ton of people does not mean you can no longer do good deeds but when it comes to dating that person–yuck! People who don’t sleep around typically wouldn’t want a person who sleeps with a bunch of people. It’s not the decent thing to do. It’s no coincidence that people lie about how many people they’ve slept with. People that don’t sleep around have no problem being honest about it. Sleeping around does not automatically make you a bad person. It just means you have a problem that you need to work on, especially if you want a serious relationship.

        1. My last boyfriend had only slept with two people before me and he was the biggest jerk. Didn’t know how to treat a woman with respect so I dumped him. Likewise I have dated players that have decided to take dating more seriously and pursue a committed relationship and they have treated me very well. Numbers mean nothing.

          1. EJ, I’m glad you dumped that jerk and I hope you have found someone who takes relationships seriously and is respectful. I will use your example to further explain my position. ( none of my following comments are about you personally EJ)
            First, find out if the person is a jerk. They are? Okay then don’t date them. Find someone else. It doesn’t matter how many people the jerk has slept with because they are a jerk and nobody wants to sleep with a jerk anyway, so the relationship ends before you even need to ask.
            So now you’ve finally found someone who is not a jerk? Awesome! But wait, you say they’ve been sleeping with loads of people? Whoa! This person may otherwise be nice but they live a kind of yucky lifestyle and clearly have a problem. It’s a character flaw worth investigating before you proceed otherwise you may become little more than just another number. If you do not care then maybe you deserve one another. Leave the cream of the crop for the rest of us who actually value relationships, otherwise, step your game up. Do better and choose better.

  • I wouldn’t want to know about his numbers. We don’t live in the past. Past is irrelevant. It doesn’t say anything about the person’s character.

    But I want to add that things are different now thanks to facepoop. Everyone’s dirty laundry is out there. You can see the whole dating history when you scroll down on their timeline. That is something I don’t like. I think people should keep their private lives to themselves unless they are very serious in the relationship. That timeline dating history kills all the mystery, for me anyways. It also tells me that you are an insecure guy and you are trying to prove something to everyone by showing your every date to the whole world on fb. So having sleeping too many people in the past doesn’t matter, displaying them all on fb. does matter.

    When someone asks me I say “There are kids walking without shoes in some part of the world right now, you are not going to dwell on my past, are you?” And, I really mean it. Once you realize that you need to get over yourself, you don’t worry about trivial things like past dates. You enjoy the moment.

    Best xxxx

  • I was recently asked that question for the first time, and I’m old! I was taken aback and somewhat defensive as I felt like, WTF? what business is that of yours. I didn’t say that of course : ) I told the person that I didn’t know and if I did know, I don’t think it would be appropriate to answer because it’s irrelevant. Huge warning sign that this guy was jealous and possessive and went on to act out in other ways. If you like that kind of guy great, but not for me. I think it’s childish, insecure and un-evolved.

    1. I agree, Janet. It is childish to dig it too much. I used to ask and be asked this kind of questions when I was in college. I think, it is sweet to be a little jealous, it is human nature, but the person shouldn’t take it too far. When an adult, mature person judges you based on your past, it looks very self-absorbed and obnoxious to me. xx

  • I was asked this not too long ago by someone I really liked. He thought it was crazy that I didn’t readily know the answer. Of course, he knew and could name everyone he slept with (as if I really cared to know). I asked him if he thought I made a notch on the bed post every time…hahaha!! I admit that the question caught me off guard, not because I have this crazy number but for the fact that it’s the past & really insignificant (in my opinion). Good video, thank you!!

  • I don’t think there’s a blanket response for this question.

    If you’re casually sleeping with someone, then yes, the question is ugly and the answer shouldn’t matter. If the question is coming from someone with whom you’re invested, however, the answer matters–not because of the number itself, but because it indicates how your partner feels about sex.

    The way someone feels about sex speaks on his/her other moral philosophies. I don’t care about an exact number, but sex is something I value and it’s important for me to know how my partner views what we’re doing. For example, perhaps a guy has had few partners…is it because of religious reasons? Is it because he’s only wanted to have sex within the confines of monogamous relationships? Or if a guy had his “wild oats sowing days,” it can actually be quite flattering to know you’re the game changer, or that he he considers sex with you as something altogether different.

    So, the number itself doesn’t matter, but it’s nice to know where someone is coming from and why.

  • The answer is YES and NO…..but I would not ask it the same way as your question – it would be something like – how many relationships have you had previously? It does not matter whether the relationship lasted one week if you want to count it as a relationship and give me your answer. Nor does it matter if there was sex involved or not. BUT what really matters to me is to know how many women you have been with, as it gives me an idea the kind of man you are. I say this because I don’t give my body easily – and there could be a waiting period before sex is involved so if you are the tye of man who gives himself easily then to me that suggests you are not looking for a connection first and connection is everything to me.

  • As long as a man knows how to flick my switch ;), meets my standards of how a relationship should be and treats me with respect, I don’t care how many women he has slept with.

  • Sorry Matt I completely disagree with this answer.

    I think it’s an immature way of dodging a VERY important question!

    So you wouldn’t want to know if the girl you were dating or marrying had been a prostitute? Then one day before you were meant to get married you find out she’d slept with 100s of people (this happened to my friend)

    If two people are close enough to share the most intimate experience possible with each other (that naturally would lead to creating another human life) then it would seem very irresponsible to not know basic facts about the other person and their past, character, morals, values etc.

    1. You can’t retrieve a persons character, standards, morals, values etc. from a number.

      A number doesn’t tell you what their sexual style/fantasies fetishes/libido/orientation etc. are.
      Maybe the person does or doesn’t have much interest in the party scene and that wo9uld effect the answer.
      Maybe you live in an area where there are or aren’t alot of your type (say race f.eks).
      As Alissa was saying, maybe you are a virgin simply because your standard hasn’t been met yet – and that can be the case if you have been sick in a hospital for a period of time, and not because your standard/preference in lifestyle/relationship with your body and how close linked sex end love are.

      It also depends on how private/secretive you are (how big of a deel it is to you to be seen naked fx).

      And your social skills/flirting skills. Do you know how to score the guy you want, and say no to him when/if needed.

      Did you go to college, do you drink, are you comfortable with how you look naked. …

      You can’t conclude from a number whether it was right for that person to hook up with those people – nor can you say that having a low level of experience is preferred by that person, maybe you were a geek and wish you had had more sex.

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