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.

  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!

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