My Boyfriend is Wonderful, but Not Ambitious or Successful

My Boyfriend is Wonderful, but Not Ambitious or Successful

Hi Evan,

I have been struggling with the fact I have a wonderful man in my life who loves me more than I’ve ever felt loved, but I’m just not satisfied somehow. We have known one another for about ten years dating on and off, taking a four year break at one point. He is VERY persistent and continues to take me back into his life if I let him. We are compatible on many levels, but there is one thing that continues to turn me off (from ten years ago to now) and that is his lack of ambition to be successful professionally. I wouldn’t be picky about his career field of choice but at the rate it’s going I’ll never see him in a 6 o’clock loosened tie… which is a huge turn on for me.

I’m very much that young professional go getter with the high stress job, always moving to the next promotion. I’m busy all the time professionally and personally because I thrive on feeling accomplished. He on the other hand is satisfied with bringing home an okay pay check to put food on his table, not that concerned with finishing college (he’s 31) and rarely has anything interesting to talk about outside of “us”, movies, and other media outlet driven conversation. A full day of freedom in my life does not revolve around TV, 90% of his would.

I can’t let go of wishing he were a stronger, more creative, more successful man who I could look to for experienced life advice. I’m very independent but I’d also like to get some reassurance and empathy from a reliable source from time to time. I know that’s harsh. I would never say those things to him, but it’s how I feel. I find the sexiest thing about a man is his intelligence, and no matter if a person is well read or not, a great deal of intelligence comes from professional life experience. Please tell me I’m being too hard on him and myself.  I should be happy to have a man who loves me and I can trust.


Thank you, CJ, for writing one of the most self-aware letters I’ve run. I think everyone here can feel your pain. Love is only easy when we’re so whipped that we can’t even think clearly. In such circumstances, there are no decisions to be made. But right now, you’re seeing things quite clearly. Which means the world is grey, not black and white.

Love is only easy when we’re so whipped that we can’t even think clearly.

So before I get into talking about him, let’s talk about you.

You’re not a gold-digger for wanting a guy who is more ambitious.
You’re not snobby for finding intelligence sexy.
You’re not shallow for craving conversation that doesn’t revolve around pop culture.
And you’re not wrong for wishing he were stronger, more creative, and more experienced professionally.

The questions that linger for me are these….

1)    Are compatibility and kindness more important than worldliness and ambition?
2)    Is it realistic to think that you can find a worldly, professional man who is as kind and compatible as your current boyfriend?

This is the calculus of dating. And the same answers don’t apply to everyone. Which is why giving advice on such individual matters is somewhere between impossible and pointless.

But that doesn’t mean I can’t try.

Someone told me recently that women expect men to fulfill ALL of their needs, which sets them up for failure. They want men to fulfill the role of their best girlfriend and their rock solid Marlboro Man simultaneously. As I said in “Men Don’t Go Both Ways” chapter of “Why You’re Still Single”, these are different men and you’ll always be disappointed if you expect a man to cover all bases. Strangely, this is one area in which I think men “get it” more. We can compartmentalize. Which is why we’d rather watch football with only the guys, while you’d like us to come shoe shopping with you.

Point is, it’s a failing proposition to expect one man to be all things to you. Thus, you have to make hard choices. What’s most important to you? And what things can you NOT get from anyone BUT your boyfriend?

I’ve wrestled with that myself, because, like you, I get a rise out of ambition, philosophy, and creativity. Who doesn’t? But I can talk to my business coach about my business, I can talk to my best guy friend about philosophy, and I can experience my own creativity and others’ creativity in 1000 other forms. But I can’t make love to my business coach. I can’t wake up next to my best guy friend. And with all the art and culture out in the world, I don’t need my spouse to be a creator as much as an appreciator.

I get the joy of sophistication. It’s fun to feel like the witty, urbane couple that can break bread with the prime minister if need be. Just know that apart from the spark you feel around a sophisticate, it doesn’t have much inherent value. The ability to quote Proust pales in comparison with the person who will drive you to your chemo treatments in thirty years.

The ability to quote Proust pales in comparison with the person who will drive you to your chemo treatments in thirty years.

So, back to the original question: are compatibility and kindness more important than worldliness and ambition? Well, if it were either kindness OR worldliness, I’d say yes. But there are ambitious people who are kind as well. And it would be easy to tell you to dump your guy and seek one of these guys out. The thing is that most good qualities often come with bad qualities as well. The ambitious guy may work 70 hours a week. The sophisticated guy may be a know-it-all and a snob. You just don’t know until you put yourself out there. There’s a pretty big risk in doing so.

I would encourage you to look long and hard at what really matters, CJ, and how hard it is to find it. For years, I said that I wasn’t jealous of any of my married friends because it’s not like they married MY wife. And I meant it – I never really met anyone with whom I was super-compatible. But now that I have someone with whom I’m super-compatible, my mind succumbs to the temptation – what if there’s someone else? Someone younger. Someone more accomplished. Someone more well-read.

Is there someone like that out there? Maybe. But she wouldn’t have the number one quality that my girlfriend has: she accepts me as I am, and loves me unconditionally. No other girlfriend I’ve ever had has done that. Which is why I’m keeping her and never letting her go.

I can’t say what’s right for you, my friend. Intellectual stimulation matters. Money definitely matters. But if you can get stimulation from other people and you can make money yourself, why not land the one thing you can’t get anywhere else – a partner for life?

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  1. 151

    Hunter 150 – what do you mean by this? Can you explain? Are we women supposed to go gaga over that kind of man?

  2. 152


    ….can’t see what I said, got moderated…..

  3. 153

    This topic actually made me realize something I have never considered, yet alone thought of. So I say a partner for life is the ultimate human expirance!!!

  4. 154

    hes not gonna change…i was in the same situation – i was 35 successful and dying to get married and have children so i gave a chance to a man who was a loser and had no ambition or a cent to his name who was older than me – since he was in love with me i thoguht better than nothing and to stop being picky and at least he was good to me….i am now battling the courts because he wants spousal support even though he left me for a younger woman now that he sponged off me and doesnt need me. The reason cjs bf is purseuing her is because no other woman wants a loser like that and he knows this – these men are gold diggers and once you have kids with them the law forces you to support them forever. I wish i had stayed single because all my hard work was for nothing and now i am struggling to support 2 children and a deadbeat loser dad of theirs and his new gf because she is too lazy to work.

  5. 155

    This was a wonderful answer. I’ve felt this way sometimes, and I have a wonderful partner who loves me unconditionally. Thank you for this different point of view.

  6. 156

    Wow. This is the best answer I have ever read to a dating question.

    Bravo. You’ve helped a lot.

  7. 157

    All these responses about her having to suck it up are ridiculous. It’s hard to have respect for someone who has no drive to do anything. There’s no reason a man can’t be an awesome guy AND be driven and ambitious. And being ambitious doesn’t always equate to a mega millionaire coke-fiend.  

  8. 158

    Okay. NOW I GET IT 🙂

  9. 159

    somehow I find something lacking. totally understand her situation. I think what she finds is that he is not improving himself for the past 10years. or new topic to talk about I think it is unhealthy for couple to stat stagnant. it is suppose to be empowering and understand each other’s desire and goals. I think what is lacking is both need to set goals both hope to achieve be it philantrophy work. if he refuse. he is pretty much stagnant and he need to do a lot of self reflection. same with her of what she need and want. I think couples should never stop growing, learning, understand and empower each other. ot is so crucial. I mind if my man is less ambitious. he doesnt have to be reaching to the top of corporate ladder but he has to think outside the box and be different. one is moving while another ia not is not really good. unless balance is found.

  10. 160

    How about love?! True freakin’ good ol’ fashioned pure genuine love?! Love doesn’t see incomes, wealth, assets, etc….not true love anyway. So I have to disagree with those who suggest being on the same financial level as their spouse is key. When you know, you know and the other person too will know and a bank account balance shouldn’t change that…this person wouldn’t expect you to financially support them, only to love them. We forget all about the power of love in the face of money, success, and the ways of the modern world….love and let love, people. My boyfriend makes significantly less than I and it has never and will never be an issue. We throw it all in one account, pay all our bills accordingly, enjoy life as our dual incomes allow (what’s his is mine, what’s mine is his) and just spend the rest of our time loving one another. When you find your true love, you will provide for one another in ways that money never could. I have found that and am never letting it go.

    1. 160.1

      But what about when that spark fades, as they tend to do? How long have you been together with this person, if I may ask.

      1. 160.1.1

        Perils of a long, thought provoking thread, I guess. Nice job and I’m certain intentional, Evan. 🙂

        Please see my last entry. And keep in mind, you ask a very important, great question. There will simply be several perspectives to it, and that’s okay. It’s why we’re here …


  11. 161


    I am having the same problem, and understand where you are coming from. I would also like my boyfriend to be both a professional or at least more intellectually stimulating, and he is not.
    For me, I think it is far from me being an unappreciative, evil wench. I actually think that it is a problem that he does not even understand my ambitions and wonder if he would be able to support me in them.

    Gender relations is a big deal in this kind of relationship. If you are a high earner or at least professionally ambitious you need someone to support you. And non-professional men still think of women as supporting them in their careers. I do not think that someone is more generous or has a better disposition just because they’re not professionals, or are worse because they are. There are also professional men, that do not seek relationships, they just seek entertainment or dating multiple women because they have the wealth to do so.

    It really all comes down to the individual person. My question is simple: If you lived with this man and had children with them, do you think he would really help you out at home, fix the house, contribute to the household economy, and perhaps take gender atypical duty (like taking care of the children more or cooking) because he understands that is what he has to do to SUPPORT YOU in your ambitions? Or will you end up pushing yourself careerwise, and doing the housework? Because the latter is a very heavy load for a woman to carry, and anyone that does not understand that is not being fair to you.

    You’ve known your boyfriend for 10 years, so only you would know if he is willing to cook your meals once in a while, or if he really just watches television while you work yourself to death in your professional role, only to come home and cook for him. To me, that is definitely a sign, not just of lack of professional ambition, but also of laziness, lack of personal ambition and lack of understanding of what your partner needs.

    All the best.

  12. 162

    I would run. Unless you want to spend $1000 a month on alimony and child support. That’s my life with someone that can’t hold their own.

  13. 163

    I agree so much with Evan. Good qualities come with bad qualities. I know. 
    The outgoing popular guy is also addicted to attention, the successful ambitious guy is also self absorbed & always puts his work/ career first, the intense romantic guy is only looking for an ego stroke & runs when the ‘chemistry/ excitement’ isn’t as intense anymore. Best to find someone who is committed, kind, won’t leave you then forever looking for the illusion of the exciting, intense love of your life who gives you butterflies and a feeling of ‘awe’…..

  14. 164

    This was the answer that I was searching for. Thank you for great words of wisdom to help me with my predicament!

  15. 165

    I am having the same problem now. But your answer was absolutely what I need. Thank you!

  16. 166
    Lakita Bryant

    I really needed that I have a good man who loves and cherish me,thank you so much he will be my husband.

  17. 167

    Insightful read, especially since my boyfriend is passed out drunk from a day out with his buddies. 

  18. 168

    When something about someone you are dating annoys you, the fundamental issue is that this is an area in which the two of you are different.  What you need to do is to get to the root of why this difference annoys you so much.

    You could be extrapolating: you may have preconceived and potentially incorrect notions about what this behavior says about the person you are dating as a whole.  In this particular case, does his lack of ambition and cultural capital mean he is a lesser person?  Or does it just mean that he values different qualities in life?  You need to figure out if this difference is something that you could learn to understand or if you are going to be judging him for it for the rest of his life.

    As many others have posted, although this is an area of difference for the two of you, there is still a possibility for compromise. You could send him articles/video clips that you would like him to discuss with you, or introduce him to new experiences.  Also, just because he doesn’t have the life experience to offer you advice doesn’t mean he can’t support you in other ways.  You have to decide what’s most important to you and how much the two of you can grow for each other.

  19. 169
    Dina Strange

    I wish i could agree with a lot of commenters here about the fact that if a guy is stable, caring, being ambitious and driven is not important. Alas, it comes down to respect. Personally, I dated those nice, stable ones, without any desire to improve their minds and or careers, and it just doesn’t work.

    I was bored, and at some point stopped respecting them, because myself am driven by intellectual pursuits and innate curiosity. But for each its own. At the same time if a man is driven but a jerk, has no time for you, and puts you as his third priority it also won’t work. Has to be balance.

    1. 169.1

      Exactly! All these negative comments on here. You can find a better balance, it doesn’t have to be one extreme.

  20. 170

    If youre not ambitious or successful yourself.
    You dont deserve an ambitious or successful man 

  21. 171

    ambitious men with big hearts are out there, ive met some! charmed me to bits! but lets be honest here, those rich succesful charmers who also are kind, sensitive, wanting commitment, family and all that, they can attract skinny 5 ft 10 leggy model types wif perfect skin and are You good enuff in Their eyes? can u hold their love after marriage when those other stylish beauties are swarming near the man like flies? some women aer more insecure and need the man to focus on them so much, thats easier when the man thinks hes getting someone a lil out of his league. thats probably why CJ’s man keeps taking her back. i think CJ should stae wif this guy! anywae i luvvv this post!

    1. 171.1


      …..there is truth in your words…. 

  22. 172

    I never once read her saying that she loves him! 

  23. 173

    This issue resonates with my relationship right now with my boyfriend.
    I am 23 and he is 28 will be turning 29 in a couple of months. We are both educated and posses a Bachelors Degree. However, I am starting my own business, pursuing my masters degree and am always talking about my future. The downside is that my boyfriend, although having a BA in Marketing, works at Apple. He loves to work out and is passionate about tech. He says he wants to be in the Marketing Tech business and eventually start his own business, but he doesn’t say what kind of business nor does he talk about his future. It is always about fitness, family, and his current position at Apple, a genius worker. Now the reason why I bring up this issue is because we talked about long term. However, I don’t see him being as ambitious as I am. He never talks about his future plans unless I ask him and when I do ask him, he doesn’t answer me with a plan. Instead, he says I judge him and that I have this criteria that he doesn’t meet. I love him to death. The thing is that it is a turn off that he is not taking his career as seriously as me. Furthermore, he doesn’t want to pursue a higher education. Not that it’s a big deal, but he will be 30 soon. Time is ticking and I don’t think he realizes that. Additionally, he wants to marry me, but I don’t see my parents blessing our marriage let alone do I feel that he will be able to support us both, especially since I’ll have student loans, intend to open up my own clinic, and a non-profit! 

    I feel bad that I have been so open and honest with him. It’s just that I really want him to stick around, but promise me that he will be more of a man (sorry to say this) and assure me that he can take care of us and that he is doing x,y, and z to ensure that, so that we can eventually get a home and marry!

    ughh. However, all this conversation has made him feel bad and he is beginning to resent me. He has already asked me if I have thought about being someone who is professionally driven like me. Here is the bad thing, I do think about it sometimes because I know that in marriage not only does love come with it, but also circumstances.


  24. 174

    wow!this is the best have read nor heard!!I see anyone lg none wto dbut hhoices in the end are left out to the person to decide!

  25. 175

    I have a similar situation but my girlfriend wants me to guarantee success
     .Which is impossible to predict, I have all the drive and ambition to try whatever it takes but she wants the guarantee.
    We’ve been dating for about a year now and it’s the greatest relationship for both of us.She has no debt and $500k or more in 401K and savings.
     I have $35,000 in debt and she is aware I am taking care of it.
     Everything else is perfect 🙂 But we decided to move on together and this has come up again.I told her I can’t promise I can only promise to try as hard as I can. I think to promise more is asking me to lie almost.
    I know she truly loves me and I love her but she keeps bringing this up.
    We are both 46 and I make good money and my debt will be gone in a year. She always wants to partner up to start a business with me down the road. But she also is scared to risk her money  on any idea. She could retire now if she wanted to but she wants more money.She pretty much said if I am not successful down the road then she would leave me.She is also very controlling and I told her I would be able to be successful if she lets me do it my way.As nice as I am and sweet and loving she still comes back to that.I guess a nice guy who helps clean,gives great back rubs and foot rubs,cooks and makes good money isn’t good enough unless I become a millionaire. 🙁

  26. 176

    Thank you so much for this insightful post. I’m in a somewhat similar situation myself, although different because I’m a high school senior with a boyfriend who is perfect in almost every way…except he is extremely lazy. Despite his parents urges and mine, he hasn’t done anything along the lines of finding a job, getting his permit, or really trying in anything. I, however, am extremely motivated and take pride in the fact that I am a hardworking individual, for the most part, anyway. I gave him an ultimatum: get off your butt by graduation or it, unfortunately, is over. Reason being, I don’t want to waste my life with someone who, no matter much I love and am satisfied with, I have to bite back constant criticism. 

    You shouldn’t wait around for Mr. Right. Either stay with your current man and settle, or leave. Don’t string him along as you search for the one you want. 

  27. 177

    RUN!!!!! And run very fast from this relationship.  A guy who would spend his time glue to the TV! I was with a man like that before and after six years until I realized that eventhough he was a good man I could not spend my life in front of a TV hoping that we can do something mich better than that.   If you ever have children with him shat do you want to teach your children????? 

  28. 178

    Oh my gosh I have the same problem with CJ and I am so thankful I found this blog. Thaank you so much!

  29. 179

    Most women who are truly successful in the business world are insanely unappealing as a mate/partner. It’s just the reality. CJ sounds like a complete pain in the ass and this guy needs to be thankful when she dumps him. She just can’t get anything any better so she is staying. In the end, all women settle.

  30. 180

    I felt a little better after I read your answer, Evan! I’m going through the same problem that the girl above. I have a boyfriend (almost 3 years of relationship) who loves me, cares about me, I really like being in his company. But he’s 30, still lives with his mom and he is not the breadwinner type of guy. I mean, he works, but his current job pays barely enough to cover his minimum monthly expenses. And the worst part is I’m not sure I have faith in his professional money-making abilities. I’m not sure he can give me the type of life I want. Don’t get me wrong, I’m not the gold digger kind of girl, I don’t want him to support me. I simply would like my life partner to be able to share the home expenses (I don’t want to be the one who pays all the bills) and to pull his own weight and possibly “carry” me temporarily should I need it — and I would do the same for him. If I stay with him, I can totally see a life where I’m bringing home the food while he’s the stay-at-home dad … which might be nice for some women, but that is NOT the life for me. To me it is much more exciting a man who is the provider, I really feel frustrated with the idea of my boyfriend being a “househusband”. it is frustrating when your boyfriend earns a salary less than yours. I’m afraid of breaking up with him and never finding a man who is also kind and the provider, the breadwinner guy. On the other hand, I’m afraid of marrying my actual boyfriend and never having the type of life I’ve always dreamt to me.

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