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. Click here to learn 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.”

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.

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. 31

    It’s not rocket science. If you aren’t into the guy then leave him. Stop playing with his feelings. And I am sure another woman with some common sense would take the guy. If he bores you why keep him around? Why not suggest some things? What type of excitement is needed?
    If I had a nice woman doing those things for me how the hell would I complain? What girls try to do is change guys that are bad and disrespect them. People change themselves. I know so many of my aunts and cousins who had at least 3 great guys in their lives and they found the smallest reasons to pick at them. And now some of them are bitter and lonely or in a delusional marriage.

    Guys are held responsible for a lot of things they do and don’t do. It’s like women want us to tackle lions and stuff. I mean agree. Nobody wants a doormat. But if a respectful and nice, that’s just it. I’m a nice guy myself. I’m not into treating women all screwed up. But I am far from a doormat–and many have tested me and lost.  I have wised up and learned how to not be on the back burner and an orbiter. people have the right to like what they like is what I say. But I tell you, age does get old. And when you are on the other side of 30, single mom, screwed a few guys, those “nice” decent guys will start to look good.  And when the single moms start saying: he’s gotta be this, and that, and this. I just shake my head. Because every kid you have your value goes down. And if you got a guy writing you letters, being somewhat chivalrous, you need to wake up. But what I came to notice as my 6 yrs of dating. Women do not know what they exactly want until they get too old or have kids.  Yes physical attraction is important. That’s a given. But to nit pick at every small thing the good guy does, and then make every excuse on why to keep the bad guy, it’s pretty self-explanatory on how your date life will end up. 

  2. 32

    I was married to a man for 16 years who said to me “you know what your problem is? You are too nice, nobody likes nice”…Previous to his comment I tried very hard to convince him it’s important for us to try an activity together or just be alone without the kids once a week, but he complained that if I want to hire a sitter weekly just to go out then I shouldn’t have gotten pregnant. He was the boring one and then he became verbally abusive. So, take my advice, misery will never work into a great relationship, so you are not selfish, it’s just that he is not your match. Don’t date boring guys or “too nice” because you will only break his heart down the road. Date your type which is the adventurous type with “living in the moment” attitude without a plan.

  3. 33

    What a bunch of selfish assholes in the world… only concerned with having the right partner rather than being the right partner. If I were a man, I’d think this women wasn’t worth my time. I couldn’t give a damn about how beautiful, strong, or independent she is. She lacks conviction.

    And how about keeping your pants on until you figure out whether or not your interests, core values, relationship expectations, and long-term goals are in alignment? That might do you some good.

    Stop fucking every guy you date. 

  4. 34

    I think the key statement here is:
    “He is completely into me.”

    What of HIMSELF does he bring to the relationship? Or is it all about YOU?

    I’m engaged to a great listener, after a long relationship with a lousy one with whom I felt abandoned. He’s pretty good at feedback, and keeping the conversation going. But when I’m done talking about my day, my interests, the new things I’m doing… he doesn’t have much to say. He goes into his usual “kind mode”, tells me how he loves me, how great I am. This isn’t shallow flattery. This is who he is. He is very very kind, and very very loyal, and helpful, and all those other good things.

    But he doesn’t do a lot else than get swallowed into me, however much I encourage him to NOT make me the center of his life. (Interestingly, he also has a history of “psychos”.)

    This guy sounds the same way.

    I can have this comfort for the rest of my life. But I also know that any new excitement in this relationship is going to have to come from ME. Am I ready for that? Maybe, as I’m good at constantly finding new things, and I’m quite independent also. Maybe it will be enough to come home to great hugs, a good listener, good dinner (he also does all the cooking!!)… to come home to a …. mirror of me.

    I have another three months to decide…

  5. 35

    Ok so after reading all of these posts about…”i was with a nice guy and he bored me….” or “lust and love have to be an equal part of the equation”…look here is the hard truth…LOVE IS NOT REAL….its basically a temporary madness that occurs when two people are ATTRACTED to each other and then eventually fades away….Nice guys generally have a harder time with women because they tend to be..well…nice. The bad boys have a clear monopoly over women because they are generally better looking and they are more narcissistic and impulsive which most women misinterpret as confidence and strong charisma. But then they are left in shambles because the bad boy will always find a hotter girl and nothing will stop them because they know the hotter girl will be as crazy about them as the previous conquest. So yeah…basically women and nice guys are screwed…sorry…

    1. 35.1
      Karmic Equation

      You’re wrong, Sergio. LOVE exists. UNCONDITIONAL love (outside of parental love for their children) is what doesn’t exist.

      Romantic love SHOULD be conditional. Should anyone stay in an abusive relationship? No.

      Romantic love should be conditioned on the other partner’s willingness and effort to maintain and grow the relationship in a healthy way. Once either party starts shirking their responsibility to the health of their relationship, the affected party needs to make some difficult decisions and have the courage to walk away.

  6. 36

    Here’s a twist to my story…met my boyfriend(father of my daughter and has a 5 year old son from a previous relationship) from an STD dating site. We were diagnosed with herpes. (Tmi but so far we haven’t had any outbreaks since our first outbreak, thank God.) We dated for 6 months, he was a nice guy, I was attracted but not the physical type I would usually go for. Within those 5 months, he asked me 3 times to be his girlfriend, each time I wasn’t sure and kept saying I wasn’t ready for a relationship, as I was still in love (head over heels) with my Ex (good guy, super attracted, personal trainer, entrepreneur, challenged me) and heartbroken (because of the herpes news) in that 6 yr relationship. By the 6th month (although I was not fully over my Ex) I decided to give him a shot. By month 8, I got pregnant and basically moved in with him. I have been with him for almost 2.5 years. Long story short, since day one he’s been a home body: cooks, cleans, washes clothes, works full time and also watches the kids when I go out with the girls or to the gym. When we’re out he’s social but at home he just sits on the couch and watches tv all day. He’s not into sports or any other activities although if I plan an outting with the kids or just us he’s fine with going for the most part. The sex is good but I’ve had better. Now this may sound all good, and it is but I just don’t feel like he brings the best out in me. He’s not the brightest star in the sky but has some decent common sense. I just feel bored at times. He’s not interested in doing anything other than watch movies all damn day or go out IF I plan it. Intellectual conversations and spontaneity is not something he’s into, opposit of me. We’re the epitome of introvert v. extrovert. I have love for him but not in love head over heels and often question the future with him (at times he can make immature comments, turn off). Am I being selfish for feeling this way? I also don’t want to separate my family just because he can be boring and not add much when it comes to growing together in a relationship. It just feels as though I’m doing alot to stay interested and he’s doing a whole lot of nothing. Fyi I’m 28 and he’s 31. If I decide to break things off, it’ll be very challenging to find someone else like him (minus the introvert) given my situation + a child. Bottom line: I’m damned if I do and damned if I don’t.

  7. 37
    lol crazy

    This entire response confirmed by the final words, was the longest nicest way of telling her she is crazy I’ve ever seen. She has what she wants but doesn’t want it cuz it doesn’t not want her. lmao sounds coco for cocopuffs, she wants the kind of guy she can have a reason to push away! These girls (and I say girls purposely) are not women they are girls living adult lives. A real woman grows out of this frame of thinking especially when she has children. Do you want your children to grow up with out a father figure or to grow and chase after the same worthless men you have had so far? Their is more at steak here than you childish vanity.

  8. 38

    I hate when guys pounce on girls who want “nice guys”, but then dump them. Lemme explain something here: we DO want nice guys. Every bad guy treats us like crap and a person can only take so much of that; so when we’re over it, we never want to deal with that again. We’re not intrigued by jerks, we don’t like emotional pain. What we DO like is chemistry.
    Chemistry. That indefinable spark that can turn friends to lovers, and a relationship to new heights. Chemistry: it’s there or it’s not.
    Women have a 6th sense in picking up on it. For women, sex is very emotional, and if we’re not feeling it, it’s just an act. Guys don’t really mind too much if sex is good, bad, whatever (good sex is preferable, but some sex is better than none, right?) Women don’t see it like that. And, because society tells us to be sweet, don’t hurt people’s feelings and be people pleasers in general, we pull away. Trouble is, you guys can’t ever take a hint. You think we’re playing “hard to get”. Ooh, fun, the game is afoot! Chase is on!
    No, no, no. We didn’t like you and don’t want to sleep with you because we feel nothing. Take the last guy I dated: looked great on paper, but I couldn’t get him to converse with me. Dinner felt like an interview with yes and no answers. I’m Diane Sawyer and his lawyer’s not present. Total dial tone. After giving up on trying to talk about him, I go quiet for a full 10 minutes while he gulps his food, then we head to the movies, then I go home. Next day, he asks to go for coffee. I decide to give him another chance. Same thing. One final date- we go bar hopping, still no convo, no sexy gazes, nothing. I go home ready to write this off, and he’s driving me crazy! Texts, calls, begging to see me. WHY? WHY?! I repeat my question, WHY?! Can’t he see there’s nothing there? Neither one of us excited or even having fun. But, the more aloof I get, the worse he is about chasing. And, this is after having drunk sex on our third date I really regretted, so I know it isn’t that he “didn’t score”. No, I don’t like him, so he’s going to work to MAKE me like him. Eventually, I’ll have to tell him not interested, and no matter how gently I do it, he’ll twist it to his friends to make me seem like a b*#@% who led him on. Get some clues, guys.

  9. 39

    I forgot that I answered this article a long time ago. Lol
    People are seeming to confuse being introverted and extroverted with treating people wrong or right. A guy can be introverted and still treat a woman bad. It’s about the personality. Now true, if the chemistry isn’t there; then it isn’t there. But, what I have always found out is that women will often sleuth out reasons on why to NOT keep the good guy i.e. he doesn’t do too much of this, or there’s gotta be something wrong with him.
    But often, I’ll here women that have bad guys say; at least I know he’s bad–at least I can see it coming. BUT…also, predictability in a good guy is seen as boring.

    What is your excitement level? If your excitement threshold is high, then it would not make sense for you to stay with a person who does not satisfy it. You cannot change people–people change themselves.

    In many cases though I have personally seen women make every excuse in the book on why they want to keep the bad guy around (and in some cases it’s: because I love him). But that is their problem. It all starts in the home. The women that go after those guys, virtually don’t know what a real man is. Because in most cases they grew up without one in the home. If a girl chooses that crazy bad guy then she is a grown woman, let her have that choice she’s entitled to–and go and get you a woman that suits you better.

    One story I got. I met a 19-year-old woman on DateHookup. The thing is that she lived 45 miles away. I had no car. No other ways of getting to her (and I clearly didn’t think it was worth it). I was about to quit the date site, and she messaged me–and without a profile picture.
    We talked a lot to eachother and shared a ton. But in the end, I cut it loose. We still talked though.

    But my gripes were that she was not aggressive enough for me. I have grown up around a strong woman; my mom. And I expected my woman to be the same. But that is unfair of me. I should like my woman for who she is regardless. The woman I met is very introverted and shy–mostly because of her family. I actually got to meet her for the first time in 3 years last week.
    It was amazing. And she was not so bad. We had a slight argument about her introvertedness.
    But then I got some sense slapped into me.
    Somebody said: She’s shy and introverted, and you don’t like it. She is who she is. You should leave her alone and stop trying to change her.

    They were right. I like her for who she is. The shy and introvertedness is something she will change herself sometimes. But who knows. Maybe I am a person that gives her confidence regarding that?

  10. 40
    Leslie G

    You have received a lot of comments and information on your question. My input to this is: if you find him boring at this point, it doesn’t usually change with time. If he is putting forth his best and you find him boring, let him go. Your not doing him any favors by spending time with him and him thinking more of this relationship than you do.

  11. 41
    Aracely Macken-Estilista

    Hola, muy bueno el post, muy util, lo compartire. Abrazos a todos

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