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.

Join our conversation (179 Comments).
Click Here To Leave Your Comment Below.


  1. 61

    I was in a relationship last year with similar situation. Although he had strings of unfortunate and short past relationships, he seems like a decent guy, and I thought his breakups were because he hasn’t met “the one”.   *Sigh * I thought I could change him when the time is right.  

    It started innocent enough, he needs time with the boys, liked lots of space, loved making new friends. Instead of spending lots of time with me he would rather go drinking with his friends. Later, he started to ask strange women he met at gatherings for their phone numbers and out to dinner secretly. Whenever I confronted him, he always says he is just making new   friends. I wasn’t comfortable about his action, but told myself I should trust him, and which successful and self-absorbed guy isn’t flirty or attracting to other women.   Again, I thought he would settle down when he  finally   grows up and can start viewing a  monogamy  relationships as a bliss instead of burden.  

    Sad to say I was very  surprised  when he broke up with me for another woman after a year relationship.   He was just waiting for someone better to come along before he would leave me.   I agree with what Evan says– trust your gut feeling.  Deep down I knew all along that he was looking to trade up, that’s why his  behaviors  were so  disturbing  to me.   When a relationship feels wrong, it probably is wrong.     

    The best relationship advice I would give myself is, besides attractions and personality,   find a man you can fully trust and love him unconditionally.  

  2. 62

    @ Ellen: What makes you assume that Ana’s friend isn’t good-looking as well? Her boyfriend sounds like an an inconsiderate clod. And what should she do? Tell him, in front of their friends, that his behavior is unacceptable.
    Really, I’m not getting the “boys will be boys” mentality that claims that it is acceptable to leer at other women in front of your significant other. My boyfriend might comment that a certain celebrity is attractive, but he will not talk about her nice ass or boobs to me. Why would he think I would want to hear that?

  3. 63

    Ugh, can we ever have these discussions without it turning into a post about how much men use and abuse women?   

    Seriously, some men cheat, some women cheat.   Some men are dishonest, some women are dishonest.

    The point is that you shouldn’t treat every man (or women) like a cad just b/c some are.   Keep your eyes open b/c people will always show you who they really are, even if SOME of them can hide it for longer periods of time than others.

    I personally think that flirts are not more likely to be cheaters since cheating involves hiding what you are like.   And it’s nice to be around people who make you feel good and I am capable of understanding that most people who flirt with me do not want to run away with me.   

  4. 64

    Henriette: ”What should my small-breasted, brunette friend do when her boyfriend announces, loudly, at a dinner out with friends that he loooooves big-boobed blondes the instant the waitress fitting that description saunters away from the table?”

    Well, as a small boobed woman myself, what I would do in this situation is say ” God yes, David is crazy for big boobed blondes…. You know this one time, he drove over a senior citizen with his shopping  cart in the mall when this booby blonde woman appeared –   the poor old man was crippled, we had to call an ambulance….” or something of that sort… At the end of the day, the guy is with the small breasted brunette, so how seriously interested in the blonde waitresses can he be??!     As even points out, its not really what men say its what the do that matters, and if this guy has chosen a small breasted brunette for a partner… well, it speaks for itself. Equally, as a woman, I might remark on a particularly fit looking 20 something guy in front of my partner, but at 47, I’d be quite staggered if he seriously took that to mean I wanted that young guy as my boyfriend – it would be simply absurd! Have some common sense, people!

    1. 64.1
      Evan Marc Katz

      Thanks to Helene and Nicole for bringing us back to reality. If you think men are the enemy, you’re not only blind, but you’re likely to drive any good man away with your negative beliefs.

      I know this is a forum for advice – and with that, some venting is inevitable – but I’m always amazed at how anyone who fundamentally doesn’t trust men or is hypersensitive to real thoughts from real men (yes, like me) can function in a long-term relationship.

      My litmus test is that if you ever get mad at me (not disagree with me) for something I wrote here, I would pity anyone who has to date you. Chances are, you don’t care to understand men, listen to logic, or deal well when reality doesn’t conform to your fantasies about how things should be.

  5. 65

    @ Evan #69: I totally get what you’re saying and it is 100% true, but unfortunately trusting men after you’ve been ”burned” so much is easier than done. I don’t hate men, I don’t even like the word hate, and I don’t get mad, but women complain and are insecure for a reason… I do want a great, healthy, happy relationship, it’s just that the more experience I’ve got, the more I see and hear, the less I believe in men.
    @helene #68: Ok, he might be with the small-breasted brunette, but still it’s offensive and disrepectful… I don’t think people realize how much of a ”punch in the stomach” it can be. Plus, I think there are guys who are in relationships just for the sake of being in a relationship, and not ’cause they really love their girlfriends… I think a comment like that might leave Henriette’s friend wondering ”Why is he with me then? Does he even care about me?”, which causes terrible insecurities. I’m not saying he should think the waitress is ugly, but if she’s so relevant that he dhumiliates his partner because of her than you can’t expect the gf to be cool…

  6. 66

    What men say matters if a the comment is demeaning or humiliating. There are people who are emotionally abusive who are never physically abusive, but that doesn’t make the emotional disrespect okay. Besides, the man going on and on about the waitress could ask her out quite easily. Maybe busty blonds have always been his fantasy partner, and he merely settled for the brunette, who knows? If making a joke about it suits you, great, but I wouldn’t just sit there in silence.
    The vast majority of my coupled friends have never cheated on their partners (to my knowledge), and never would. And no, I don’t hate men. I have a wonderful boyfriend (who was not easy to find, btw), and my best friend is a guy. It’s easy to be positive around by boyfriend because he’s kind and thoughtful. But not all men are created equal. Isn’t that the point of this blog? To find the nice guys and avoid the jerks?

  7. 67

    I would tend to agree with Ana and Ruby that a man who makes that comment is classless and likely emotionally abusive. No one who actually cares about their partner goes out of their way to  embarrass  them.

  8. 68

    As Ernest Hemingway wrote:
    “The best way to find out if you can trust somebody is to trust them.”

  9. 69

    @ Katrina
    “David in my experience any man who flirts is easy pickings for a bit of naughty time!
    I have tested it and asked them straight if they would like a bj and not one has ever turned me down!
    Not one!”
    You are observing a biased sample – men who flirt with you.
    Which goes back to what I said about indications of infidelity being more conspicuous, and thus tending to dominate our  perceptions.
    For the record, I don’t flirt – as I think doing so when attached is the height of boorishness.
    @ Ileana
    “Is it wise to ‘test’ your partner in such ways- Send him anonymous texts and see if he replies?”
    That depends on if you would define ‘cheating’ to include responding to anonymous texts.
    “Or is this just plain rude?”
    Only if it becomes obvious – and then it is more stupid then rude.
    But, if I was tested in this manner by someone I love, I can’t honestly say it would bother me(she would just be wasting her  time).
    “Why would somebody, male or female, who is in a happy relationship and gets all their needs met, still feel the need to  cheat?”
    Because, men want sex.
    Lots of sex.
    With lots of different women.
    Those with means and opportunities will exploit them, unless they are exceptions who are poorly sexually motivated,  are risk averse(and feel their SO justifies their fidelity), or have been socialized to be sexually passive(ie. they were  ugly ducklings who were discouraged through a history of rejection).
    “wouldn’t it be A LOT easier to end the relationship and start a new one, instead of cheating?”
    No, because they see their LTR as security to fall back on when the casual pickings are slim.
    @ Wendy
    “It’s not like they wear t-shirts with “CHEATER” on the front, so please tell me how I’m “choosing” players!”
    No one is telling you that.
    However, that is what YOU are telling us.
    “The bottom line is, I have to believe that there is a man out there who feels as strongly as I do that a solid, loving,  respectful relationship is better than the “excitement” of a little on the side.”
    There probably is – one who is sexually passive, without options, or a risk averse male who will be satisfied not to risk  your affections.
    The question is, will you be attracted to such a man?
    I think the limiting factor for all problems of relationship stability, is an increasing tendency to disassortative mating.
    Most single women I have observed(in the OLD demographic), are ignoring their nearest male equivalents in favor of  interacting with more attractive options, even where these interactions are invariably short-term(they would rather play the  longest odds, than make any concessions towards more stable interactions) – to these women, I would say that securing a LTR  is evidently a low priority(even if they fail to realize it).

    1. 69.1
      Evan Marc Katz

      @Paragon – Dude, get out of your black and white, biological evolutionary bubble.

      You said that the only man who believes in a solid, loving, respectful relationship is one who is “sexually passive, without options, or a risk averse male who will be satisfied not to risk your affections.”

      What are you, a lower mammal? A neanderthal who can’t override his biological impulse to spread his seed?

      There are millions and millions of married faithful men who stay faithful because what they GAIN from their monogamy is GREATER than the thrill of random sex and infidelity.

      It’s a choice, bro. I’m the first to acknowledge that I’m always attracted to other women. But as a sexually aggressive guy who had many options when he was single, it wouldn’t occur to me that throwing my marriage away for a cheap thrill would be a good idea.

      Stop trying to speak for good men who knew when to retire from screwing around and sincerely want to grow old alone with a life partner. Evidently, you don’t know crap about us.

  10. 70

    I have to say Evan, I so agree with you @ 75.

    My life is replete with good, solid men of integrity who would never dream of cheating on their wives, despite whatever biological impulses they might have. This is the model I was raised with, this is how my brothers were raised, and most of the guys I know. I have never been cheated on (to my knowledge).

    I can  *only* speak from my own experience, I know, and not to deny the experience of others, but I would submit that faithful men are in fact everywhere you look 🙂  

  11. 71
    David T

    Thank you, Evan. Yeah, it turns out humans are more than their lizard brain.   This gets swept under the rug in these blog discussions often when people lay out laws about how men and woman should behave   in dating situations “because we evolved that way.” huh?
    @71,72 and many others.
    You make a judgement based on your own perspective about what should bother a woman. Personally, I think it is boorish (as Paragon put it; heck, I will add to that, creepy) to loudly announce “I looooove big-boobed blondes” whether you have an attached relationship or not. There are   crowds/sub-cultures where that is OK.   I accept that. There are probably relationships where it is OK too.
    If this man’s girlfriend is not OK with it and she has communicated that to him and he behaves that way anyway, it is disrespectful and emotionally abusive.
    If a woman knows her guy loves her, is faithful and she is content with her body image, no matter what he admires physically, then that is not going to bother her. If it doesn’t bother her, it isn’t emotionally abusive.    
    Don’t automatically judge what should bother someone, just because it would bother you. That is presumptuous.

  12. 72

    @ Evan Marc Katz

    ”  What are you, a lower mammal? A neanderthal who can’t override his biological impulse to spread his seed?
    There are millions and millions of married faithful men who stay faithful because what they GAIN from their monogamy is GREATER than the thrill of random sex and infidelity.”

    But, that’s what I mean when I specify ‘a risk averse male who will be satisfied not to risk your affections'(I just had a more dispassionate way of describing this).

    I was not trying to conflate all three qualities that I recognized
    as contributing factors.  

    Also, I don’t consider ‘risk-averse’ as a derogatory characterization.  

    ”  It’s a choice, bro. I’m the first to acknowledge that I’m always attracted to other women. But as a sexually aggressive guy who had many options when he was single, it wouldn’t occur to me that throwing my marriage away for a cheap thrill would be a good idea.”

    You won’t get any argument from me about this(again, I just have an alternate way of describing the factors that mediate these kinds of cognitive biases).   

    “Stop trying to speak for good men who knew when to retire from screwing around and sincerely want to grow old alone with a life partner. Evidently, you don’t know crap about us.”  

    I think you have misinterpreted what I have said, for which I must accept some blame.

    Still, I’m not certain we have any real disagreement here.  

  13. 73

    @ Ana,

    I can relate.   Which is why I love reading the dating blogs, because it makes me feel like now I have a good toolbox full of tools to handle dating and a relationship.   I feel less like a victim and now know how to set good boundaries, not allow a guy to trample all over me, and to hold out for the decent guys, not just the ones looking for a quick shag and run.

    It IS hard to trust after being burned, trust me I know.   But I’m learning how to do it, bit by bit.   It’s not easy and yes it is easy to jump to conclusions sometimes.   But not every guy is an asshole or a cheater.   Not every guy will break my heart.   It’s sure taken alot of wasted evenings with twits, to meet my guy, but hey there we are.   At least I’ve learned alot about myself along the way, had the opportunity to put what I have learned, into practice.   I never stood up to men, til two years ago.   I never said sorry but I won’t allow you to treat me like crap.   Now I am empowered, strong, and able to handle a guy.   Even nowadays, my current guy is rather snippy and cranky for whatever reason, and I used to get sick to my stomach, when a guy would do that. Now, I know it’s not about me, that is on them, and that it is more than OK to tell him, you are not allowed to talk to me like that.

  14. 74

    Evan, I think you and Paragon are actually seeing more eye-to-eye than you realize in these last two comments. Being a “risk averse male” is not a bad thing. In fact, it is a very good thing, as it shows the ability to reason and to decide what the best actions are in a given circumstance. You yourself demonstrate risk aversion in your next-to-last paragraph. You do, as you say earlier, override your biological impulse to spread your seed because you’re smart enough to realize that you achieve greater happiness and satisfaction by not “throwing my marriage away for a cheap thrill.”
    The way I see it, a man can be good, sexually aggressive, and risk averse all at the same time.   The last shows cleverness, which women always hold in high regard.

  15. 75

    I gotta agree with paragon here in some respects. A man who has fewer options is simply a wiser choice for marriage. Sorry, Evan, but sexually aggressive men with lots of options are not worth the risk for most women. SOME of you guys will be faithful, but it’s not a lottery that I’d ever want to play. Its obvious that you are a good guy and your wife is lucky to have you , but in general, who wants a guy that stuck his dick in 50 plus women and had a different girlfriend every month? Do I really want to wake up next to some alpha player for the rest of my life and have this guy raise my daughters? How do I trust such a man? I’d feel a lot better with a 6 who had some options but not too many options.  

  16. 76

    David T #77
    Henriiette originally wrote (#15), “I don’t mind if my guy notices a pretty woman but what if it’s obvious to everyone in the room that he’s leering at her?   What should my small-breasted, brunette friend do when her boyfriend announces, loudly, at a dinner out with friends that he loooooves big-boobed blondes the instant the waitress fitting that description saunters away from the table?”
    To me, this didn’t sound like Henriette’s friend was okay with her boyfriend’s remarks. As you stated, if her friend was okay with it, and laughed it off, Henriette would probably shrugged off the behavior herself, and wouldn’t have posted about it here with the implication that it was problematic. Announcing something like this in front of friends is also an inconsiderate way to behave around those who might be made uncomfortable by that kind of talk, as Henriette was.
    As far as sexually aggressive men go, some guys sow their wild oats when they’re younger, but curtail that behavior as they get older and decide to settle down, whether they are very good-looking or not.

  17. 77

    Actually, we don’t know for sure if Henriette was present or not, but if she wasn’t and her friend told her about it, the friend probably wasn’t too happy.

  18. 78

    To Paragon #74 (and everyone else who says people “choose” cheaters and players: I am not telling you, or anyone, that  I choose the wrong men. I do not have ESP,  they do not announce  their predisposition to cheat, and they  don’t behave the way one would typically expect a cheater to act. The man I  used in my example was home every night. I had zero indication there was anything going on. Many of us are completely blind-sided when we find out there’s another woman. So by your logic I could say that if you get into an auto accident on your way to work one day,  it was your fault because you “chose” that route. The insurance companies would love that!

  19. 79
    David T

    @Ruby 82 Henriette knows the situation with her friend and we don’t, so we must trust her judgement there.
    A generalization was implied and run with by the thread, leading to the conclusion that such behavior is always   abusive. I was addressing that generalization, not the case of Henriette’s friend and her bf(*) in particular. I was not trying to say her friend was not hurt by her b/f remarks. My use of the direct quote made my attack on the generalization ambiguous.  
    (*) The man does not know how to behave in public IMO.   I would be annoyed by hearing that (and would probably tell him so), even if I didn’t   know him and was sitting   across the room. Different people have different behavior standards. I manage to avoid being subjected to that kind of behavior by not hanging out with the kinds of people who (I imagine) frequent places like Hooters.

  20. 80
    David T

      Does he sample a grape at the grocery store. . . and then if it is good try another one and another one and another one?   Does he cheat on his taxes? Does he give people lame or no birthday gifts and then complain about what he gets? Was he compassionate? How ethical was he in his relationships with other people?   Did he show them one face and then in confidence disclose to you or others how he really felt?   Was he honest with them?  
    Some of that laundry list might seem like little things that have no bearing on a relationship but the fact is, if someone is dishonest in the little parts of their life, they might or might not be in the more important parts.   If they are compassionate and honest and open when it comes to little things, I would be very surprised if they are different when it come to the big ones that would hurt other people.

Leave a Reply

Your email address will not be published. Required fields are marked *