My Boyfriend is Wonderful, but Not Ambitious or Successful

a man relaxing on the couch

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. 221

    Ok I have been in a similar situation for 20 years. I have sticked it out miserably because of my son and I was raised without a father. I have always been independent and just wanted my bf to be in a position to help me if I should fall..About 5 months ago I lost my job the guy I’m with have always contribute to his half of our living arrangement. It’s best to walk away if this is important to you.   At one point my guy was sick and because he has no ambition to get a career he works minimum wage jobs with no benefit. I had to work double job to keep up with the mortgage and his bills. You cannot change anyone .. everyone has important values. I have even gone as far as paying for my bf school ..register him …He only went a few time and stop. We live pay checque to pay checque and I have a son plus have to cover some of his bills when he is short.   Not to mention his adult daughter just migrate n lives with us while she finish school. NOW MY son is older i have curse run him he won’t leave.. he never put a $$$ down on our place yet I have to hire a lawyer to pay over $5000.00 to sell n get out of this because he refuse to sell.   I have also bought a BMW that he promised to pay off fast by working odd jobs.. i bought it because he does not make enough and have bad credit.   now he pays exact amount for car that will take 8 yrs. I have learned my bf has no ambition yet he hangs unto and boast about our place n the car.   I could write a book about my experience in short think about your happiness and who will pay his bills when he lost his job or in between jobs. How about retirement?   How about kids do u want to work as hard as me to care for ur child 17 yrs?   I need no man to provide for me when I’m capable of working I just want to have a back up if I fall. I did not have any more children because of this situation. Walk away and stay strong don’t look back.

  2. 222

    I am very grateful to have found this article. Bravo!

  3. 223

    I have a very similar example to give from first hand experience. I got married quite early at the age of 24 with my boyfriend who was studying to be lawyer from a top institute. We are extremely compatible in terms of our interests etc. But after the first year of marriage all hell broke loose. He failed his law and completely quit it after the second year. He started studying for government exams and didn’t make the cut for it. And now he has gone back to studying law from a university which has no standing here ( which means an income of $3000 per annum to start with ). Although on paper it looks as though   he has been trying to work or make something of his life , he has been only watching tv and movies ever since the  second year of our marriage. I have been working up until now and the month before the last I had to quit my job. Finding another will take me at least a couple of months (I am a designer in a country where jobs are pretty hard to come by for designers). My husband being unemployed and no prospects of earning for another year and half has hit me so hard.   I’m going to be 31   soon and would like to start a family soon.   But I keep questioning myself how. How do I do that to my children? How do I knowingly, that we would not be able to give them an average lifestyle think of having kids. I had a very good childhood, never had any demands not met. At least financially my parents took care of us. My husband has been fighting with ,everyday for delaying to have children.

    The only thing I told him when we got married was I will have children only we are at the position of at least providing a basic life for our kids. Are you ready for having a future and raising your kids knowing you could have given them a better life???


    1. 223.1

      It’s obvious you want a guy who can provide a better income. Why don’t YOU try to find a better paying job instead of insisting he do things? Just an idea…. 🙂

      Best of luck.


  4. 224

    It is interesting that she keeps going back. Wonder what would happen if he finally said enough was enough and moved on with his happy life.

    1. 224.1


      A lot of women, even in 2018, still expect the guy to be the breadwinner.

  5. 225

    Does this person bring out the best you, that you can be? Everyone has a different situation – but if this guy helps elevate the person you are inside and brings out your fire and drive, that is a positive and is building teammate.

    However – if the lack of ambition have taken a toll on your career and who you are as a person, then perhaps you need to look elsewhere. And have you clearly voiced/communicated these concerns if they are happeneing to you??

    Your partner should bring out the best in you. There is a reason you are drawn but it is up to you to figure out is those are reasons enough to stay. Best of luck! I am rooting for your happiness!!

  6. 226
    Mai Ly

    I can’t read the rest of the answer, where can I find it?

  7. 227
    Jennifer Nguyen

    Is it just me or I can’t find Evan’s response anywhere?!

  8. 228

    Knowing there is always a topic that relates to your problems is soothing. Thank you Evan for this post

  9. 229
    Jessica Staller

    This was a very powerful response. And one that I also consider deep down under all the frustration and misunderstandings. It definitely answered my question. Maybe I need to be more supportive to him so I can get what I need from him. to forgive him for his past :-/

  10. 230

    I really like Evan’s article, but there is a problem in convincing yourself that way to be with someone.  I was in a similar situation when I was younger.  I was at a point where I was working on my career and I was dating someone that was just floating through life.  After a while I started loosing respect for my partner and no amount of rational thinking could change that.  When he started talking about pop culture I was so bored I couldn’t follow the conversation.  When I spoke about things that interest me, he said I was making it up and would google it.  He started dismissing everything I said.  He didn’t want to go out with me and my friends because he thought we were just showing off who knows more.  Eventually there was nothing left in the relationship and we had to separate.  It started out passionately, but due to intellectual incompatibility things fell apart.

  11. 231

    Great article and good response. That said, I can’t  help turning the tables and looking at this from the other angle. The sweet, yet dumb, unambitious wife sitting at home, watching tv, getting fat. She has never been considered a zen genius, condemned instead for being lazy. My opinion is that powerful men often are content without an equal, yet powerful women think they would like one.

  12. 232

    Wow so many mixed opinions. And I can see all sides. Evan you’re phenomenal. That’s #1.

    I’m on my second time around for the good ol’ marriage. I am a cultured, worldly, successful woman with two young kids. He comes to this relationship with two kids, $19k in debt and a looney tune for an ex that tortures him (and me) daily if we allow it. So all together we have 4 kids under 9 years old. I’m getting my MBA in a one year program and he’s in the wrong business for him and hates it. Neglected as a child. Seems secure but is not. Not a whole lot of self worth. Drop dead gorgeous but doesn’t know it. And hilarious. Worships me in a non annoying way. Brilliant in the creative arena but ADHD that I have sadly watched cripple him in everyday life. His family discarded him like the trash. There is a reason  for me sharing this:

    My point is, the two of us have our fair share of odds stacked against us. That said, this article changed my perspective on a great deal. Or it sealed my envelope on what if’s. As has my daily gratitude practice. The line that got me in this was the chemotherapy part. At 40 years old, I am clear on what matters. At least, what matters to me. Is it going to say on his grave stone that he was intellectual and worldly and worked 80 hour weeks? Or is it going to say he was an honest, devoted, committed lover and best friend and father? The latter. So that’s the key. LOVE, the word itself, the feeling, doesn’t conquer all. Love the verb does because it’s a daily act. Acceptance and compromise and sacrifice and being there and pulling through when you don’t feel like it.

    So my harsh advice here is BUCK UP and stop any passive aggressive comments and stop just trying and stop the bullshit. TALK ABOUT IT. TOGETHER. Air it out. Talk about what you’re both thinking – without a doubt you both know this is the elephant. Use healthy conflict resolution if you argue. There are ways to communicate your needs and “fight right” and listen to what he wants and needs that will result in action. Meaning you will either split up or you won’t. But then at least you will know. All of this limbo is just keeping you both stuck. And it’s somewhat of an excuse as you enable it.  Good luck CJ. Big of you to come clean to us.

    PS Relationships are about acceptance that’s all that really matters at the end of the day.  are these things that you can accept  truly in your heart and not want to change in the future? believe me he has things he’s accepted about you as well. are these things that you can accept truly in your heart? I’m wondering about the level of security you have within yourself and  I wonder whose definition of success you are going by when you say all of this – since you’re projecting so much of this on to him that actually is within you.

  13. 233

    I really needed to read these wise words. Thank you so much Evan.

  14. 234

    She should set the poor man free. It sounds like no matter what he does professionally, she’ll escalate for more. Ambition, like education, is no guaranty of success. People aren’t ATMs or storybook characters that can be molded on the whim of adolescent fantasies. If she wants more money, she should go and make some more. If he’s following his own path, and happy, he should find a better gf.

  15. 235

    Let him go.
    Cj is ambitious. Virtually by definition, ambitious people are not satisfied with what they have and this drives them yo push for more ..continually. this is both good and bad.
    Its good because continually pushing for more independant of what you already have accomplished is EXACTLY how growth happens – both personal growth AND that is also how the world progresses.

    Cj- your bf just wants a nice comfortablr and easy existence . He does not want to push himself outside of hhis comfort zone to realise growth opportunities for himself nor do things that positively impact thr world (I’m talking about big things, not little day to day standard course of business things).

    I am not saying your bf is right nor wrong…and neither are you right nor wrong.
    All I am saying is that this is actually a serious mismatch of goals, values drivers , directions in life etc.
    These are serious things that are different.
    Please go..for both your sakes.
    The problem for you cj would be that most proplr (men and women) are closer to your boyfriends level than to yours.
    So, it may br a bit tough yo find what you are looking for.
    But you cannot give up!!! There are men out there that fit this criteria.
    I am a man that has similar outlook at what cj does and can feelnypur pain. Its not easy for men who want this from females either, as most females are similar to where your boyfriend is.

  16. 236

    I don’t think it’s right to tell CJ that she’s asking for too much,she’s not at all and wanting an ambitious man is really important for a woman that is ambitious .you aren’t superficial at all and even if you aren’t going to end things because of this,resentment is going to grow in your relationship and poison your love

  17. 237

    Vee, I agree. It’s possible to see that a couple is not compatible without casting harsh judgment on either side. In CJ’s letter, it’s pretty obvious that they would not be happy together in the long run. While I think she is a little naive in wanting the 6 o’clock loosened tie (an ambitious man doesn’t always wear a tie, and that same man may be very irate after a long work day and not be able to fulfill her as she wants), she is well within her rights to search for what she wants. One thing for certain, though: she should not return again to this man who likes to sit and watch TV all day. None of her disdain of him will have vanished.

  18. 238

    I really needed to read this. Remind myself what is important. Thank you.

  19. 239

    I completely disagree here.
    While some women and men do look towards partners to fulfil all their needs, most often people are taught to settle from society, their parents, ect.
    I think what’s going on is that as this woman’s gotten older, shes gotten more successful, and her partner hasnt. While as a younger women in her 20’s this is fine for most, as you’re not thinking about anything like kids, a house, a mortgage.
    But if shes older and successful and he isnt, you start to worry that you’re going to be the one moving the whole thing alone. It’s less even about success, more proactivity. Proactive people are more likely to be helpful and bring the relationship up, whereas less proactive people are happy to mull along. That’s fine either way.
    But this woman clearly wants a match, an equal. It seems she has lost some respect for this guy, or simply, they do not have matching values.
    All this rubbish about, women, you cant have it all. Pick kind or ambitious. All this rubbish about gold digging. Youd never say that if this was an ambitious man.
    Rise to the top lady and if he cant keep up, he is dead weight. Dont make yourself smaller to be with someone.

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