How Can I Learn To Trust A Man And Give Him Freedom?

How Do I Cope With the Other Women in His Life?

Hello Evan,

I’m new to you, but I’m a quick student. My question is not really for you, though, it’s for your wife. Has she written anything you can refer me to? Like her, I have ALWAYS believed in giving others freedom to live their lives, make their own choices, etc. I’ve not found a man that believes that’s a 2-way street.

I’m 49, out of a 20-year marriage followed by a 2-year relationship with a “player” who took advantage of that freedom. So now I am newly on the dating scene and need a fresh belief system that doesn’t trigger those old fears.

I am interested in her perspective and/or philosophy in regards to how she “deals” with the other women in your life, particularly those you might feel attracted to. I’ve investigated the “polyamorous” and “open relationship” scenarios and I don’t really think that’s what you have or nor what I’m looking for, but how does a woman handle those situations as I do believe in people having freedom in a relationship is the only way it can work. Is this a fine line?

Thanks, Kim

I like your question, Kim, and while my wife is too busy running to Mommy and Me classes and shopping for our dinner parties to sit down and compose her own response, I did actually read her your question after dinner one night last week.

A wife trusts her husband enough to not cheat, even when there’s temptation? That’s crazy talk!

She was flattered and really wanted to give you the best possible answer. Her only recorded thoughts on dating have been compiled in a four-page section of “Why He Disappeared” and I’ve been told, much to my consternation, that her part is the best part of the whole book. I don’t know that I’d go that far — but I would say that learning how to best deal with an alpha male from the horse’s mouth is pretty invaluable. I’m quite candid that everything I teach comes from the “What Would My Wife Do?” school of thought and I think you’ll really enjoy it.

As to your provocative question about how much freedom you should give a man when you’re in an exclusive relationship and how do you deal with the inevitable fears and insecurities, allow me to set the record straight:

It is not at all difficult for my wife to deal with me, for one huge reason.

She trusts me.

Unconditionally. No question about it. Wouldn’t even occur to her that I would ever do anything to breach our vows.

She knows that I value my character and morals as highly as I value anything else in my life. The way other people value religion, I value doing the right thing.

Acceptance is the most powerful tool in making a man feel loyal to you.

And because of that worldview, there’s nothing I can do that’s remotely threatening.

This is why I can be surrounded by five attractive 30-year-old women at a party in Hollywood and I won’t get lectured when I get home.

This is why I can get a lap dance at my bachelor party in Austin, and all my wife asks me when I come home was whether I had fun.

This is why I can occasionally point out a woman in a low-cut top in a restaurant or watch online porn. Neither my wife nor I thinks that this is a slippery slope that’s going to destroy the foundation of our relationship.

This is why my wife can hire burlesque dancers to join the 80’s rock band at my 40th birthday party last month. They were a big hit with everybody — and about 10 women came up to me and told me how extraordinary my wife was. Huh?

Don’t get me wrong, my wife is extraordinary, but the only thing I think is REALLY extraordinary is how RARE this kind of behavior is.

A wife trusts her husband enough to not cheat, even when there’s temptation? That’s crazy talk!

But why? Shouldn’t ALL wives trust their husbands? I sure think so. After all, what kind of relationship do you have if you don’t trust the man you’re supposed to trust?

Thus, the first thing you have to do, Kim, is to find a man that you completely trust, without a doubt. It’s your doubts that will drive you nuts, not the man himself.

Some women would be driven nuts by me, but that doesn’t mean that there’s anything wrong with me. You may think I’m disrespectful. My wife doesn’t. She thinks I’m normal and she loves the fact that I can be myself around her without any fear of retribution. And because she’s so accepting of me — a trait I’ve found very hard to find — I love her in a way that few men openly love their wives.

Acceptance is the most powerful tool in making a man feel loyal to you.

Now that does NOT mean accepting behavior that is inherently unacceptable.

Wherever you draw the line becomes the line

Some women freak out if he talks to another woman, has lunch with another woman, says something cute on Facebook to another woman, or looks at another woman. I think this is a bad policy because it’s essentially asking him to spend his entire life lying to you and denying the existence of any other woman. If you find a man who is willing to pretend that no one else in the world is attractive but you, I applaud you and hope you’re happy.

Agonizing about whether he’s going to cheat is like agonizing about whether a plane is going to crash. You really can’t do anything about it, so you might as well try to enjoy the ride.

But since you’re a freedom-loving woman, Kim, you don’t have to do that. You just want to know how far you should go. It’s not my place to say what’s right for you, but if you believe what I do — that both sexual contact and sexual intention can be considered cheating — then that becomes your tipping point. If your boyfriend is asking for women’s numbers, flirting on, taking other women out to dinner secretly, having phone sex, or actually cheating on you, then, well, he’s broken the boundaries of exclusivity.

In other words: fantasizing, fine. Acting on his fantasies without your permission, not fine.

As long as you know your boundaries, you can give him all the leeway in the world, until he breaches your trust. Which brings me back to the three things my wife had to say about your question:

1. Go with your gut.

My wife trusts me so much that even when she had physical evidence that I was cheating on her (panties in the dryer), she still believed me when I swore that I wasn’t.

She trusted her gut.

My wife knows infidelity — she’s had three boyfriends cheat on her — and each time, she knew when something was wrong. Her wisdom was in not treating those men (or me) as if they were untrustworthy until they actually did something untrustworthy.

2. Stop looking for it.

As my wife pointed out, if he’s going to cheat on you, he’s going to cheat on you. You can’t stop it with fear or worry or interrogation or jealousy. If anything, those kinds of behaviors will be more likely to drive a man to escape. Agonizing about whether he’s going to cheat is like agonizing about whether a plane is going to crash. You really can’t do anything about it, so you might as well try to enjoy the ride.

3. Trust

As I’ve long said, it’s either full trust or no trust. If you truly trust your guy, you couldn’t even imagine him cheating on you. He has a strong moral code. He treats you like gold. Even if he’s attracted to other women, he would never think of jeopardizing his relationship for a quick fling. And so you let everything go that is not actually cheating behavior — and watch him express his further devotion and appreciation to you.

For you will be the only woman ever who has done that for him — who was confident enough to let him be himself and not try to change him.

That’s why he’ll stick with you forever.

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  1. 21

    Hey now…Go ahead and question Evan when he says his wife found panties, but don’t question his wifes self esteem. Who knows what kind of story might be behind it.  

    And clearly there is one according to Evan’s above comment (which I will now go search for). 😉

    Play fair when you call someones values into question.

  2. 22

    The panties story is both hilarious and endearing, Evan.   And so very Larry David/Curb Your Enthusiasm!   Was there ever an episode based on it?

  3. 23

    See i BELIEVE that this only works because most women are just not secure enough to fully trust their partner! I also think that what she doesn’t know can’t hurt her right? And the most successful marriages I have ever known are ones where the wife believes her marriage is hunky dory and her husband never cheats on her while he is busy having women on the side.
    My ex ex husband has a wife who actually finds other women to sleep with. They are in saudi arabia at the moment so it is difficult for men to find willing women for nsa fun. He loves his wife more then anything because she never says no to him, allows his cake and to eat it too, and she is beautiful after two children. He often says that he can’t believe his luck. I asked him if it was okay for his wife to have other men and he said his wife doesn’t want too!
    In my eyes this is completely unfair to the wife. Its as if she is settling to make him happy without any concern for herself. Of course he is happy in such an open marriage but what is the cost. Obviously being in a marriage and the luxuries that go with it are more important to her then her own self worth!
    That is an extreme case but back to the men whose wives trust them completely not to actually cheat behind her back I think its a crock and alot of men are getting off the hook here. And they know it! A friend of mine has an open marriage and his wife allows threesomes and he is always cheating on her behind her back. Yet she believes that because they are open about everything he tells her the truth.
    The fact is that women need to be more independent and men need to learn how to be grateful for what they have!
    As for trust… well it is usually undeserved but we will always have a few idiot women who truly believe her husband doesn’t succumb to temptation behind her back.

  4. 24

    Thanks and congratulations to your parents. 40 years isn’t easy by any standards.

    ” To give someone that power again is not so easy. To give it in the first place isn’t easy. Proving that you’re worthy of it is hard enough. The trust thing takes a lot more than just knowing a relationship needs it. It takes a lot of strength and values from both sides.  ”

    You’re so on point. It may take some time, but you’re definitely going to be okay.

  5. 25


    Are you saying that in all successful marriages the wife has her eyes closed while he cheats.????      I trusted my husband of 20 years so Im an idiot???   Most women aren’t secure enough to trust their partner???   What sort of people do you hang out with??  

    If you had an ex husband who has his current wife procure other women no wonder you have such a warped outlook.

  6. 26


    You’re kidding right?

    I don’t know what kind of screwed up world you grew up in, but that’s not the world I know.

    I actually have real 40+ year marriages (several) to use as an example and that’s not the case at all! All the females in those marriages are strong, commanding, intelligent women.

    If they chose to move on past infidelity at any point it was because they felt it was worth their while to do so. But I highly doubt any one of those women is the type to put up with any kind of bullshit from their man.  

  7. 27

    Feeling secure and trusting in your relationship is a wonderful feeling, and I think it comes from a number of things. And so for what it’s worth, I think they are:

    1)   Choose men of integrity. I would say place this quality close to the top of your list of requirements in a partner. You really have only yourself to blame if you are dazzled by someone who demonstrates player behaviour.

    2) Quality of your relationship. I think in a relationship where 2 people adore each other, the chances of cheating are low. What’s more, being adored brings with it its own feeling of security, as does knowing you are with someone who chooses to spend most of his free time with you.

    3) Be aware of your own boundaries / comfort level. As Evan says, this differs from person to person and couple to couple, but I think it makes sense to  choose someone who makes you (generally) comfortable, not someone who is setting off your radar on a weekly basis.

    4) Evan may not agree with me on  this, but I think the women here generally will – There are women who are drawn to men who are in committed relationships, and it’s wise to be careful of them. For me personally, it’s important to me to be with a guy who knows what he has in me, and can see these women for what they are.

    These are my own personal guidelines for being trusting in a relationship, but I really do feel that you will know the strength of your relationship by the fact that trust comes naturally. Beyond that, live and let live – don’t give your devoted guy a hard time 🙂

  8. 28

    #23 EMK:
    I think this was a good blog post and I also read and appreciated the original “panties in the dryer post”….but I too would like to know why the panties were in the dryer!   Not pointing the finger…just quite curious! : )

  9. 29

    @ Clare,

    I agree with you.   I think there really are women who are drawn to guys in committed relationships.   I’ve had friends who were involved with married men, and often that wasn’t the first married man they went for.   There are women who are drawn to what the author of the “Baggage Reclaim UK” blog calls, “Mr. Unavailable.”
    I can understand that some guys in committed relationships can be very attractive, but I also know that I’d be horrendously screwing up my karma, going after them.   Once a guy is taken, hands off.   I think it’s very rude to go after a guy whom you know is taken.   A girlfriend of mine once unknowingly went after my now ex-boyfriend, she later told me that she had no clue he was dating me, because I was never mentioned in that group of friends during happy hours, etc.   I had no problem with that and i told her so.   She didn’t know, no harm, no foul.

    Cheating is huge for me, I’ve been cheated on, a number of times, in my past.   But now I have boundaries in place, and I’ve made it clear to guys I date now.   Cheat once, you are gone, there is no second chance with me.   Done.

  10. 30

    So at point do you got from trusting the negatives to trusting the guy with integrity?   Trusting my gut this far hasn’t worked out so well for me, if it had I probably wouldn’t be reading this blog.  

    So exactly do you stop trusting the negatives?  

  11. 31

    This strategy works well when raising teenagers too :)…pre-teen, let them know you fully trust them, until they give you a reason not to, and remind them of that here and there throughout the years   That has worked very well in my household.

    This is an excellent article and how I treat the men I choose to date.  

    Helene, I loved your posts/comments.   Good luck with your new relationship!       

  12. 32

    Thank you so much, Evan, for your reply to my inquiry. The panties in the dryer story was absolutely hysterical. And having been on the receiving end of that same type of innocent accusation where there is no way to prove yourself innocent, I know THAT feeling as well. I have since learned this is a tactic used by cheaters to defray the heat from their own behavior by making up some accusation about their partner:(

    What you said,  “Thus, the first thing you have to do, Kim, is to find a man that you completely trust, without a doubt.” is exactly what I am doing. I guess it just takes time to not only trust one’s own intuition about these things, but to see if the man’s character lines up with his words. I know you say never trust the words, only the actions. There is no real way to vaccinate yourself from being deceived. It is just knowing, having been through it before, that you recognize the signs, the feeling in your gut, and realize you have the strength to walk way, and not getting caught up in the fantasy of who you THINK they are, who you WISH they were, or who you NEED them to be and just observe who they ARE. I do appreciate everyone’s comments to the post, they are all immensely helpful!

  13. 33

    I am always trusting of the men I date,  whether  they deserved my trust or not I will never know because I don’t snoop or accuse them of cheating.

  14. 34

    I have been in a similar position. After a 19 year marriage, dating was new and after being with one man so long, although I knew what I didn’t want, I was still exploring and learning what I did want and part of that was undoing old habits. Part of dating right out of a long marriage is not letting your loneliness and new found separateness blur your boundaries. But it happens, because if you were like me, and ignored during your lonely marriage, it’s easy to go with a man that shows you attention and reawakens things that were dead in you. Even if he’s a player or unavailable. I think it is common. And ladies, it’s ok. Guys make the same mistakes and we need to experience players and unavailables to better define what we need and want. Kim recognized that a player is not what she wants and is looking for a game plan to avoid getting in that situation again. It is a process of learning and trial and error until you become solid again in your new life, being single, and finding fulfillment in other areas other than a relationship. I’ve gone through several players and unavailables. Avoiding players is not about trusting them unconditionally. It’s about setting up standards beforehand and as you date and go through the getting to know stage, you constantly hold them up to your standards, trusting they will follow through, but being comfortable enough to be alone rather than staying with them, when they break your trust or cross your boundaries. If lap-dancing is crossing your boundaries, that is fine and is your boundary, no one else’s and it’s not about not trusting the man. If you think watching porn is cheating, that is fine. It’s ok if that doesn’t suit you and that’s not the kind of man you want in your life and it doesn’t mean you think he’ll cheat. You just don’t like porn in your life, just like you might not want smoking in your life. I recently dated a man that was one of the first that didn’t want to get in my pants the first couple of dates. I was thrilled because I had finally decided that this was a boundary I no longer wanted crossed. He was fun, a gentleman, a flirt, outgoing and I knew he was on match and talking to multiple women at gatherings. That was not the problem. It was his deception. He was playing the field despite his initial words and actions about caring enough about me and a relationship to go slow. He had figured out, probably in some book or men’s blog, that pretending to be a gentleman and not trying to get sex right away is the way to a woman’s heart and a way to break down her boundaries and get what he wants. And what he wanted was all the fun (physical companionship) without the work or commitment. I knew pretty soon it would be a lot of work on my part to even get close to what I needed with this man. His deceptive, immature and confusing communications were the red flags. He was not honest with himself or me and actually lied about why he didn’t contact me one time. That is what I could not trust, not how he treated or acted around other women. Being a player doesn’t just mean playing with your body, there are plenty that play with your mind and emotions.  And unfortunately, in my experience they are in the majority.  As Evan has pointed out, men want the milk without buying the cow.  But if they really want the milk and we put a price on it, they’ll buy it.  

  15. 35

    Yeah, there isn’t any way to control another person.   And if you set up lots of rules that you think will keep your man or woman from cheating, most of which are kind of ridiculous, then he/she will just lie about what they are doing.   And you are setting up a system where everything is an infraction, so you’re making someone seem worse than they are.   

    I don’t get why people think that controlling who their spouse is friends with, who he/she talks do, who his/her friends are, leads to a long, happy marriage.

    It might result in a long marriage, but it will also result in someone who probably secretly resents you, is passive aggressively lashing out at you behind your back, and who is keeping secrets that could vary from innocuous to serious just b/c they fear you and your rules.   And most importantly, the person will be unhappy and feel trapped (unless they have the courage to get out there and try again, although fear of being alone makes many people stay in unhappy and unfulfillling marriages).

    I could never live that way, so why would I expect any man to want to.   You’ll both be a lot happier and sleep better not always waiting for the shoe to drop.   Trusting someone isn’t about a power struggle.   It’s not about giving anyone power over me.   It’s actually giving me control over myself, and my feeling is that anyone who really is lying or cheating will be revealed.   But it doesn’t make me a sucker or a victim.   I don’t want to play cop.   Lying and deception takes a lot of work so you’ll always find out in the end.   And I think acting like a prison guard at home just means that it will take LONGER b/c it will encourage more secrets.

    I don’t want a husband who fears me, who can’t be himself with me, and who regrets meeting me.   And I don’t want someone to stay with me out of fear while secretly hating the sight of me.   That stuff totally happens.   Why put yourself in that situation?   

    If I trust someone who winds up being a liar, what have I lost?   I just move on.  

  16. 36

    I hate to get all biblical, but I love that saying “be wise as a serpent, gentle as a dove”. I believe in trusting your partner, while also being wise and observant. Also, I find the never say never people when it comes to cheating are often cheated on. The reality is we live in a world that makes cheating so easy and lots of women have been cheated on. And while a lot of the scenarios mentioned in this thread  are not  considered slippery slopes for some, they have been slippery slopes for  many people. Some of the most honest, trusting people have cheated, that’s the truth.  

    I think it’s important for a woman to trust her man, but he also needs to be clear about his actions and make it plain about her role in his life. If a man has a lot of female friends, the onous is on him to let his woman know that she is #1 in his life, that’s not about trust that’s common sense. These kinds of scenarios remind me why  the dating  scene can be challenging  when only women ask for relationship advice, because what men need to know about women is that we often feel insecure. It’s not a constant state of mind for most healthy women, but it happens from time to time. We live in a world where bodies of female olympic athletes are criticized and scored by the media, then we’re surprised when an average woman is a little insecure around other attractive women? Come on. Sometimes we need some re-assurance, not all the time but just a little reminder that  she’s  his priority goes a long way.

  17. 37


    I’m with you there.   I trust my boyfriend but I’ve learned to still be mindful, and to not let my emotions or my heart carry me away.   He’s actually pretty good about telling me where he’s going or whom he is with.   Thus far, I trust him, until he gives me a reason not to.   If he does stray, well then I know that I will be strong enough to curse him out, send him packing, and move on.   In that order.

    I’ve grown strong enough to know and trust my own boundaries, that they are boundaries that come out of loving and honoring myself and what I want and need out of a man, and also a need for no drama in my life.   Cheating is a very firm boundary and it has worked well for me.   I’ve dated players before, and once I’d find that out, I stopped seeing them, and a few tried to get back with me but I just made it clear that they were not what I wanted anymore and that I wanted a real commitment.

    If my man cheats, so be it.   It will be his karma and it will come back on him, not me, and reflects upon a serious lack of character on his part, not mine.   Until then, I’m just going to keep going along and assuming that I do not have a reason to not trust him.

  18. 38

    @ Katrina
    Help me understand this…
    A friend of mine has an open marriage and his wife allows threesomes and he is always cheating on her behind her back.
    Help me understand this. You state they have an “open marriage.” How does one cheat in an OPEN relationship? Do you mean he has more women than he admits to?

  19. 39

    I am sure Kim has been burned in the past (haven’t we all).   It is our choice to take that distrut to the next relationship.   We have the power to accept the new guy for every word he says..yet that damn voice in your head says “You have been burned before, don’t trust him.”….well silence taht voice.   Go with your facts and if he has never given you reason to doubt him then DON’T.   There are great guys out there…but often times a woman won’t see it simply because she has been burned in the past by a COMPLETELY DIFFERENT guy.   So, don’t push your insecurities and doubt onto a man who has shown you nothing but love and respect and honesty.

    I actually took my own advice and met a great guy..given we are having some issues now…it has NOTHING to do with trust.   I trust him 100% and it feels good.   Once a relationship is over, learn from it, and move on but do NOT bring it with you into the next relationship as it will hurt and affect it…start fresh.   Keep your lessons from the past but leave the rest….

  20. 40

    Thank you, Evan, for this brilliant post on such a foundamental topic in relationships! You really have a knack to tackle difficult and sensitive topics in a pleasant way.
    Trust really is the foundation of a solid and happy relationship. But trust has to be earned. To my opinion, the healthiest way to proceed is by assuming the best of people while being very attentive to what they say and how they behave. As other commenters have pointed it out, it’s essential to refrain from dragging past hurts in a new relationship. Take your new experience-based wisdom with you, but not any mistrust, negative assumptions and excessive boundaries. Take a dating break until you can truly start fresh and give people a true chance at earning your trust.
    A first couple of dates in public places in daylight hours is a perfectly safe and effective way to earn basic trust (showing up on time, in appropriate attire, being respectful in language and actions, etc). Then sharing more vulnerable facts of ones life and establishing boundaries, and observing their reaction would be the next step and allow to hopefully build more trust. Are they judgmental and critical or can they accept mishapps and mistakes? Can they respect boundaries or are they pressuring you to overstep them? If everything goes well over a few weeks or months, the last step is opening up to more sensitive and private matters and discover if they can truly accept you, keep confidentiality when requested, and in general make you feel safe and comfortable. Opting out is possible at any time.

    I agree that acceptance is a big part of trust. After all, what is the point of being the partner of someone you can’t accept? However I strongly believe in the right of having personal limits, therefore I would like to highlight this part from Evan‘s post:

    “Wherever you draw the line becomes the line.”

    Indeed it’s okay to not be comfortable with some behaviors and it’s okay to draw the line somewhere. There is someone for everyone. Simply observe how they live their life, ask questions about concerning matters, communicate your needs, and make the choice to continue or opt out based on your investigation.
    I’m into freedom as well, and do not intend to pressure anyone into giving their freedom up, but personally I’m not comfortable with the level of freedom that Evan and his wife offer to one another. Why? It’s because I think that relationships need two kinds of energies: NURTURE and PROTECTION. Even if you nurture your relationship to perfection (as Evan and his wife seem to be doing), you are not immune to the possibilty of future seasons of life where your nurturing energy is going to be lower, and at those times, it’s how well protected the relationship has been that will make it last through these extended periods of low nurturing energy. For example, being constantly stimulated by the other gender – physically and/or emotionally – might not have any impact during the high or neutral seasons of a relationship, but this stimulation can become a real relationship-killer in times of lows.

    The world is not black or white, like a world of people of solid character and of people of low morals. A world of people who are going to refrain from cheating, and of the ones who are going to cheat. People who cheat or not all womanizers or players. Lot of people with perfect track record of integrity have cheated. Not because they planned it, but because “it just happened”. It “just happens” when difficult circumstances and unfortunate opportunities align perfectly.
    Let’s say your marriage is hitting a low because your partner has suffered of ill health for a while and has been unavailable to nurture the relationship. They might even have been difficult to deal with. And during these trying times one of your friend/coworker/gym buddy that you had harmless weekly lunches with progressively becomes your main source of attention and emotional comfort, without you to even notice what is happening. Hey you’re used to do whatever you want, with your partner’s blessing. Add to this scenario that the friend has recently become a bit desperate themselves and ready – even unconsciously – to try their luck on you, and you have the recipe for a “it just happened” situation. No player involved. No previous red-flag behavior. Just a lack of understanding of how life works, just a lack of protection by not having a lifestyle compatible with future lows.  
    That’s why I believe that successful relationships must involve a decision to restrict willingly one’s own freedom to a reasonable degree. Not because of demands and threats of the other party, not because of insecurities, but because of common sense. A relationship needs nurture AND protection. Anticipating future lows is necessary. Thinking you will be immune of lows is foolish. You will hit lows. The question is not IF but WHEN you will. Where you draw the line is up to you and your partner. It’s another area where to find compromise, or opt out if you can not define mutually agreed-upon limits.
    Simply granting/asking for full acceptance no matter how risky the behaviors will become under more testing circumstances does not makes me feel safe for the future. Therefore I’m making sure to cover these difficult conversations with my boyfriend to make sure we can create a safe environment, based on trust, reasonable freedom, and acceptance, but also on common sense and wisdom.


    1. 40.1

      So very well stated.

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