Am I Crazy For Wanting To Dump The Amazing Man Who Bores Me?


Dear Evan,

A little history…I’m 28, divorced with two young kids, they live at home. He is 37, divorced with one teenage kid that he sees every other weekend. Here is my dilemma…. I can’t figure out if I’m attracted to him or the fact that he’s a good guy.

You wait and pray for there to be a good guy left on this earth and finally one comes along and you find him boring or at least not challenging.

What is that? Am I crazy?

He is completely into me. Calls, writes me letters, texts, takes me out, does family outings, asks about my day, washes my car, is clean, is fit, responsible, understanding, compliments me, etc, etc. We’ve been dating two months. We don’t get too much opportunity to spend alone time so we’ve only slept with each other twice. It was okay, not mind blowing or anything. I’ve had much better, but I’ve had much worse too. He’s relatively attractive but not my usual type or taste.

Am I being picky? Any other woman would think he is a great catch. I think so as well but just…I don’t know why I can’t get into him.

He’s completely fallen for me, thinks I’m strong, independent, beautiful, good mom, etc. wants to make me happy and for me to be his “girlfriend” and I can just tell the L word is coming along any day now. I can just tell and trust me, I’m not wrong on this.

Another bit of history…

So he usually gets involved with psychos that latch on to him. That is – the complete opposite of me. I like my space and I don’t care if I never see you again. Guys come and go but my family, especially my kids, are forever. It’s one of the mottos I live by. I don’t need anyone to take care of me. A guy in my life is “nice to have” but by no means a need. I think I’m a challenge for him, which is fine. But on my side of things it’s too easy.

From experience, happily ever after doesn’t exist. Sure everyone puts their best foot forward when they’re dating but who’s to say he’ll stay like that? Am I just jaded and not giving him a real chance? Or is just the reverse that I’m just not into him? Then the dilemma becomes do I let this great guy go and regret it afterward?

Can you give some advice on this? I have no idea what to do.

Thank you.


Dear Diana,

I can only imagine that thousands of women were reading your post and nodding along at the familiarity of your situation.

It’s pretty much the human condition. The people we want don’t want us. The people who want us, we don’t want. When there’s a rare exception to that rule, we call it love.

As I see it, you’re asking a few separate questions here. Let’s break them down separately, so hopefully you can find a little clarity — or, more likely, validation, for how you feel.

Question 1: Am I crazy?

No, Diana. You’re not crazy. You may be confounding to men, but you’re definitely not crazy and definitely not wrong…. Attraction is not rational. We can break it down to its elemental components, but that thing that you feel, which draws you to a man? It’s not a choice. No more than the base attraction a man has to a woman when he sees her across a crowded room.

There has been a great deal written on this, and there’s an entire industry designed to explain to “nice guys” how to attract women. In fact, it’s been turned into such a science, that you might want to take a look at it. Check out more from one of the original masters, David DeAngelo. DeAngelo puts into plain words what you just feel in your bones: confident, decisive, witty, and somewhat unpredictable men are the most attractive. Yes, it helps if he’s cute. Sure, it helps if he has money. But the attitude that plays the best with the most women is generally some version of “cocky and funny.”

Nice guys don’t finish last. Nice guys without any balls finish last.

Of course, most women outgrow men who are so cocky that they are unable to forge bonds with a woman. But the desire for a man with a little swagger never entirely wanes. I wrote about a man’s passion and proficiency just two weeks ago. In short, a guy doesn’t have to be a jerk to do well with women. He just has to be a man.

And while I hate to keep on referencing old blog posts, some of them apply specifically to this theme, especially this one, which says:

Nice guys don’t finish last. Nice guys without any balls finish last.

Which brings me to your next question.

Question 2: Am I being picky?

Let’s see… By your admission, he “calls, writes me letters, texts, takes me out, does family outings, asks about my day, washes my car, is clean, is fit, responsible, understanding, compliments me, etc, etc.”

So what do you think? Are you being picky? Or is there something more to dating and relationships than what someone does for you?

How about how someone makes you feel?

How about how you feel about him?

I think those two things are the essence of any relationship. And I think they get lost when we start focusing on checklists.

I speak from personal experience when I mention that I have broken up with some of the nicest people you’ll ever meet. I recall a brief relationship back in 2003. She had everything on my checklist — smart, silly, cute, good family, stable job, etc. What she didn’t have — what I really needed at the time — was a backbone. I just got the sense that I’d win every argument for the rest of our lives because she was such a pushover. And that wasn’t something I either respected or was attracted to. I broke up with her for a woman who was like a Sex and the City character come to life. All New York brass and Jewish sass. After a few months of phone calls, I flew to the East Coast to go on a four-day make-it-or-break-it date.

You can guess what happened next….

Exactly as I pulled away from the darling girl who would have done anything for me, Miss NYC pulled away from me. When pressed, she said I had 90% of what she was looking for – but didn’t feel the necessary attraction to start a long-distance relationship.

Your independent “I don’t need anybody” attitude is counterproductive. With it, you will get exactly what you’re asking for. Nobody.

And, in retrospect, I’m almost positive it was because I thought she was God’s gift to man. I kissed her ass. She walked away.

Much like you’re going to do to your guy at any second.

So… Question 3: Do I let this great guy go and regret it afterward?

Needless to say, I can’t tell you what to do. You can’t force attraction. But you know that great guys don’t grow on trees.

I think the X-Factor is that you’re a 28-year-old single mom. This means that you’ve been married, so you don’t feel the need to do it again. You’ve had two kids, so you don’t hear the ticking clock. In other words, you have nothing about which to panic. You can afford to be picky. Suitors will continue to line up well into your 30’s.


Your independent “I don’t need anybody” attitude is counterproductive. With it, you will get exactly what you’re asking for. Nobody.

If that is your goal, keep pushing away the nice guys and letting the bad boys take their shots. You’ll find them attractive, but they generally won’t want to stick around with a single mom who has all your responsibilities.

As for what you should do with this guy, it sounds to me like your mind is already made up. Therefore, you have my blessing to dump him. Staying with him when your heart’s not in it is doing neither of you any favors.

Just recognize that you’d actually like this guy more if he pulled away more and cared about you less.

A bit ironic, isn’t it?

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  1. 61

    Wouldn’t it be great if we all just knew more, first about ourselves, and then others.Know what you want from your life and from a partner, maybe now and in the next several years. Life it damn short. Lose someone you love and their time with you was too short.Know how you want to pursue someone, what kind of room or to what degree of freedom you’ll need to express that.Know how you want to be pursued.If nothing else, this is a start.I know many do know these things. It’d just be nice if we all just could wear name tags saying such things.People just demand and expect too dang much of others.

  2. 62

    I am in the SAME exact situation. Everyone around me thinks he’s great, he is but there are little things that drive me bonkers. If we haven’t been spending much time together he says things like ‘ima be busy all week so I won’t be able to see you for a while.’ Then every night he’s calling wanting to hang out. Kinda like he wanted to make me think I need to spend time with him before he’s “so busy”. He’ll text me and say I’m not gonna be up much longer (wanting me to call) and when I do he keeps me on the phone FOREVER. He’s always buying me things and repeats the same nice things over and over again. He invited me to go on a trip that I can’t afford, I said no and he was genuinely disappointed so I changed my mind. Now I don’t want to go but he already bought the tickets. If he would just back off and stop trying to force everything I honestly think I would really be in to him, I’ve hinted around but I think ima have to be blunt. I can’t deal with it anymore. 🤦

  3. 63
    Linh Le

    OMG. I love your respond! very straight forward  and you deserve a gold medal for sisterhood!

    Keep your good work. I will subcribe

  4. 64

    Wow. I fail to see how this constitutes a woman treating a man badly? We go into these things hopefully… trying to give it a go with someone you genuinely like, and wish you could properly fall for, but just don’t quite feel enough for in the end and recognising that rather than wanting to string someone along- that is not being cruel, it’s just what happens sometimes, to men and women. It’s a painful and difficult situation to be in, and none of it comes from selfishness or disrespect. Most people care about the other person in this scenario, and do not want to hurt them, either by leaving them or by not being able to give them the love they deserve. It’s a lose-lose situation for everyone involved, but all the woman hating going on in this thread and the clear bias of the author is rather unfortunate.  

  5. 65
    Paul Richard

    Men who are constantly consistent are boring, if you do the same things, over and over again, go to the same places, at the same times, he never mixes things up a bit, the yes dude is boring!

    I bet you never miss this guy, he is like clockwork never changing.


    If you never feel nervous around d him, the spark is gone, because it was never in him. Women need a little drama in theirs lives.

    Women need to feel that you might lose him to another woman. That other women want her man too. So mister safe drags down a relationship, he kills the spark in you to want to mate with him.


    1. 65.1
      No Name To Give

      You speak for all women?

      1. 65.1.1
        Paul Richard

        I see plenty of these guys with descent women your playing it safe him, acting as if, you do not need romance any more, dude should light you up every once in a while, at least once a week. They get use to the same cadence in life, they could easily do more, but they just want everything peaceful, and dull.

        It not about spending money, it’s about him still showing you his world, we all grow so should his desire to show you how he sees the world, hell he could just take you on short day trips, go bike riding, rent a canoe, just do something, and make the choice as to where you two are going. And make sure he takes you out at night once a week to 2 or 3 place on the one date! So the Romance Juice can flow once again!

  6. 66
    Jerald McClain

    Yes, I think this woman is absolutely crazy to dump this “amazing man who ‘bores’ (her).” The reason the grass seems greener on the other side is because it’s fake but she will have to learn her lesson the hard way. Said it before and I’ll say it again, hook-up culture destroyed real relationships. We leave the people who love us over trivial reasons (like boredom) and begin new flings over superficial ones (like her (blank) was nicer). “Love” begins after the “honeymoon phase.” But that’s one man’s opinion…

  7. 67

    Love is a choice. Feelings change… attractions change. Love is when you wake up every single day and say to yourself that this is the person you choose.

    The woman asking this question is choosing emotionally unavailable men. That’s her choice. Let’s not try to make her feel like a victim of fate. She controls who she chooses to love, and that’s why she is divorced with 2 kids. She is crazy, and broken… like most of the women in the west who are frankly worthless as mates. Look around… a huge chunk of guys are marrying women from other countries because the women here refuse to take responsibility for their actions and never bother to learn even the most basic emotional control.

  8. 68

    As a woman who’s had a series of pretty happy relationships, I gotta tell you, passion is overrated. I experienced it at 16 and it panned out to exactly nothing. I experienced it again with my current man and its faded at around year 3. And he’s the most interesting man I’ve ever met. He’s still an attractive man by any standard. Passion doesn’t last very long. Make sure you like the person and find him at least a little bit attractive. And then love him enough to give him “the cookie” when you can find it in yourself.

    I have a middle aged friend who said she would constantly want to rip the clothes off her husband when they first started dating. Now they’re going through a harrowing divorce. It’s not that he’s a bad guy or anything. They just had precious little in common as people. So I go with Lori Gottlieb on this one. Settle for good enough. Seriously. The perfect guy doesn’t exist. Just make sure you like each other as people. No matter how much you want to strip a guy naked now, chances are in 20 years you won’t. Hell, for most of us, I give us 3 years, tops. So unless you want to change partners every couple of years (if you even can. Dating after 40 is not easy), be sober about whether or not enduring passion is a realistic thing to aim for.

  9. 69
    Susie Smith

    She’s just not into you dude.  Move on.

  10. 70

    I am a 68 yr old woman who was widowed three yrs ago. I am slim, have a pretty face with hardly any wrinkles, and my hair is dark blonde. I met a retired professional 70 yr old widower last year and we have been dating three to four times a week ever since. I was married 39 yrs so I was totally shy and uneasy around strangers. On our first date we met for lunch, and as I sat across the table from him, he suddenly asks me if I like sex….. My first reaction was to get up and walk out, but something made me step up to the challenge, and I goes….. Ohhhhh, yeahhhh. I love sex…. To which he spins around in his chair and spits his coffee out laughing. As soon as I saw him laugh, I knew he was “THE” one. We talked for close to three hours, and when he walked me to my car he kissed me, and I it was electric. It didn’t take long into the relationship to know we both were “in love” and that we were very lucky to have found each other even as old as we are. Hey, if we only have ten more years together, I will take it as I feel like I have never loved a man as much as I love this one, and he feels the same about me…. It truly is a miracle.

  11. 71

    I am currently in this situation by the original poster. However I have to say the last line about it being ironic if they guy pulled away she would want him more is definitely false in my case. They guy I’m dating has no conversation, has not lived or had real life experiences, spends so much time with his mom and dad, we have NOTHING in common!! He also grew up in the church so he is shy and extremely modest. If I’m honest he is definitely physically different from my normal choices. But he is a “nice guy”. I don’t want him to pull away. I want him to just do something. There isn’t much to him. I’m extremely opposite, I have a lot of personality. I’m breaking up with him. He needs someone who likes what he has to offer, whatever that is.

    I’d also like to say to guys… make sure you are actually a “nice guy “. Sometimes you guys lay it on too heavy that it becomes creepy and Excessive. The perfect example of this is the series “You”.

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