Learn More About My New Book, Love Life

How To Date Ambitious Men

Ambition as we all know is a universally attractive trait. While a wildly ambitious man might not be for everyone (it can certainly take huge sacrifice to make things work with one), for those of you after one, here’s how to do it…

Enter Stephen

Are you after a man with a plan?

Sounds good.

Let’s talk about how to handle the power hungry maniac.

It’s easy to be attracted to ambitious men. Matt has often spoken in his seminars about the importance of certainty in attraction – so it’s little surprise that women are turned on when a man has big ideas about what he wants and makes strides towards his dreams.

Ambition and determination are frequently cited by women, alongside confidence, as traits that are inherently sexy in a man. And ambitious men are turned on by women who encourage their ambition.

Note: I say nothing in this piece about the importance of ambition in women, which is equally as crucial to attraction, and the subject of a future post.

Men are strongly driven to succeed by fantasies of sex and power (and even the latter I imagine is desired as a route to the former). Both are responsible for all manner of great and terrible historical deeds.

When a guy wants to show off his master plan for his future to a woman, it’s his way of puffing out his chest and displaying a unique ability only he possesses. It’s his competitive instinct saying: “stay with me, and you’ll see why I’m so much more amazing than other guys”.

Within the first few dates an ambitious guy will typically open up to you about his dreams and plans. He’ll paint a vivid picture of where he wants to be and how he’s moving towards the lifestyle he envisions for himself. This is his way of trying to entrance you. He can’t hypnotize you by applying lipstick mid-conversation, but what he can do is show off.

He will also indirectly talk about his proudest achievements as evidence that he’s capable of accomplishing big things. Sometimes this is shameless bragging. If pushed too far it can become downright vulgar and a turn-off.

But let’s assume he’s doing ok, getting excited telling you what he wants to achieve and offering a detailed vision of his life in the next few years. What’s the best way to respond to it?

DON’T… Giggle or belittle him

If you make him sound silly or suggest that his ideas are a wild long shot that will probably never happen, you’ll just either (a) make him feel stupid for thinking big, or (b) be added to the long list of people he yearns to prove wrong.

Either way, you’ll kill his attraction and cause him to emotionally check out of the relationship.

He needs to feel that what he’s doing is possible. If his plan sounds enormous i.e. he wants a penthouse in London and New York and to be CEO of the biggest software company in the world, just get excited about it with him and be curious e.g. “I love New York, where would the apartment be?”, or tell him reasons why it sounds incredible.

DO… Encourage and believe in him BIG TIME.

Ambitious men want the woman they love to be the first person they can call when something great happens; someone with whom they can celebrate every success and big opportunity. He wants to feel like you are totally on board with the vision he sees for his future, because ultimately, he wants to take you there with him.

He wants you to have an unwavering faith in his ability to succeed. In fact, he wants you to have even more faith in him than he has in himself.

DON’T… Live for his potential

Either love him as he is now, or forget it. Don’t invest in a man just because he has big ideas – it doesn’t necessarily mean he will follow through on them.

Ambitious men can go on to do great things. But it won’t change who they fundamentally are (in fact, achieving success can bring out uglier sides of a person that you may not have seen previously, so be warned).

Just because he paints a compelling picture of the future, that future could still be ten years away, and there’s no guarantee he’ll even get there. Assume he will always be the man he is now, and invest from that basis.

DO… Inspire him to do better

Ambitious men love women who inspire them to climb even higher, or dare them to think even bigger than they already do.

Encourage his abilities and even suggest at times that he’s underselling himself.

He wants you to be his biggest fan and the best coach he could ask for. The person who adores him for what he does, but also is there to push him further when he feels like quitting or when things are tough.

Just because he seems certain and headstrong, he still needs someone to push him to keep chasing after what he wants.

Every ambitious guy wants that feeling Jack Nicholson had in the film As Good As it Gets, when he tells Helen Hunt “You make me want to be a better man”. This isn’t about loving a guy for who he could be, it’s about loving him for that part of him that wants to aspire to more than he is.

DON’T… Tell him he doesn’t need ambition

You may love him as he already is, and that’s great.

But don’t bother trying to tell him to calm down or reduce his sights by telling him he doesn’t need to achieve. If he’s highly ambitious, there’s little you can say will deter him from his pursuit. The important thing is to make sure you can live with this kind of driven person. (Note: highly ambitious men aren’t for everyone!).

DO… Keep up with him and think big in your own life

The idea that ambitious men only like dependent or submissive women doesn’t bear out.

You being strong and determined in your own life is going to be sexy to him. He is going to want to give you the same support that he gets from you: the best couples are able to feed off of each other’s energy and drive each other further.

Him seeing you prioritise your own plans is going to reassure him that you’re independent and make you more intriguing.

Just don’t forget to spend time cuddling and eating pizza at least one night a week.

DON’T… Excessively poke holes in his plan

Don’t play the eternal Devil’s Advocate and explain all the possible ways he could fail.

If you become the person who always pokes holes in his plan, you become his adversary. He’ll feel antipathy towards you, and feel like he has to fight against your resistance. You don’t want to be that. You want to be in the battle with him.

All he needs to see is that you’re on his side and willing him to get there, even if he knows his ideas are a little outlandish right now.

DO… Offer your advice and expertise

Even though you want to avoid excessive criticism, you still should definitely contribute and ask questions. A headstrong guy will feel more inclined to receive advice if it comes in the form of help and curiosity rather than the critical frame of trying to “shoot down” his ideas. Suggest ways he can get there quicker, or just go ahead and take the initiative to do something that will help push him forward.

Always remember, even if they are frustrating at times, ambitious guys are basically getting out of bed in the morning to impress you.

If you show you’re on his side and have the same drive to succeed, he’ll be the best teammate you ever have.


To Follow Steve On Twitter For More Updates Click Here

Photo credit: DKShots

Free Guide

Copy & Paste These
"9 Texts No Man Can Resist"

43 Replies to “How To Date Ambitious Men”

  • I love how you have included the idea of a woman to grow along with her man. Girls shouldn’t stagnate for and put aside their dreams for thier men. But be involved in their own ambition, so the motivation is a two way street. I would love being encouraged for any of my projects that I take up in life and envious if that person makes it their baby too. I guess it’s about striking a good balance here between being encouraging and “taking over”.

    1. Absolutely – I think ambitious men really do like women who show similar qualities and have that certainty to go after what they want. Thanks Naur x

  • Hello Stephen,
    Everything you say here and in your book is so right, but your article is spot on as these men are in some ways trickier or shall we say need a certain approach. I think as a woman you need to really build the connection here. Emotional connection is crucial as there will be good times on the way to the top but there will also be bad times. You must be a support through all these but not just any support. You have to make it feel a connection like no other. Compliment and be specific but be super specific. Maybe emphasise only things you two do or enjoy about one another. Be serious and determined but be feminine, playfull, sexy and intimate. These men are used to compliments and flattery, you must make them feel special because of you, how you alone make them feel.
    Never stop having sex, these men will be having it offered on a plate from other women. Find out what their needs are, what they like and never stop thinking of ways to be original.
    Your article is great, each week your subject matter is so different, yet all of them written with such intelligence but with wit and humour, never patronising.
    Kathryn x

    1. Thanks so much Kathryn, that’s really kind of you to say. I love your advice here too – seems like you already have a lot of knowledge on the subject! x

  • Hmm, have not met many ambitious men in my neck of the woods. All in all, having insight into such an illusive creature could come in handy. Irregardless, Stephan, your blog, always a good read.


  • Hi Stephen,

    My ex husband was an ambitious man.

    I for sure can not generalize, but usually men like these, put their ambition above anything else…..not taking enough time for family, friends etc…

    I personally prefer a man who may less ambitious to achieve material things, but a man who is ambitious to grow….to be a better man!
    Don’t misunderstand, I see nothing wrong with wanting a certain style of life, but not if it means to tread on everything else.

    Most peoples minds function the opposite way….
    A question, who is in your opinion more successful?
    1. A man who build from nothing an empire, very we’ll known internationally,, divorced with children, going out with women half his age etc….or

    2. A simple married man who works in a factory a good father and husband

    Most people would answer 1

    The perfect symbiosis would be a mix of both, but it is not happening often….

    Like always you write about interesting subjects.


    1. Thanks so much Angela. Really good points in your comments – an ambition to grow is really what is important, as you say.

      All best,

      Stephen x

  • This one’s a tricky article and… I love tricky articles!! ^^

    I think THE most important piece of advice in the whole article is “DON’T… Live for his potential” to which I add: constantly ask yourself if your partner’s ambition in sync with your values.

    All these pieces of advice come handy and are great if our man has “good” ambitions. But what happens if your guy comes up to you and says “so yeah I figured I’ll rob 17 million dollars tomorrow at a bank so we can go to bora bora” well… as much as I love bora bora I don’t think I’d want to support that idea…hahaha
    I mean sure it’s cliché and common sense but always good to keep in mind, especially when blinded by lovey dovey feelings (mainly because THAT’S when we completely forget obout common sense! hahah)

    Also, and this one’s a shout out to ladies who are somewhat skeptic of ambitious men: PLEASE stop confusing “ambitious man” with “power/material/money hungry selfish wolf”. A man who wants to build a school in Ethiopia or who wants to open a soup kitchen in town or, guess what? Write a book! is as (or I’d even say MORE) ambitious than someone who wants to be the next CEO of Apple or land on Mars. I mean I don’t know about you but I think it takes a good pair of balls to even THINK on doing the first three mentioned examples, just saying… So again, let’s not fall in the trap of thinking picturing a man in a suit who only has money and fancy cars in mind, when we read or hear the expression “ambitious man”.

    Back to Stephen: As usual great work!

    Quote for this article: “Behind a great man is a great woman”-Meryll Frost ^^

    Buddy Randa

    1. I think you’re totally right about ambition Randa. It comes in many forms, and ambition in itself doesn’t just mean an obsession with money or power. It can be any burning desire to achieve or build something that requires time and effort. I agree we should definitely look closely at WHY someone is ambitious and what they are trying to attain – not all ambition is equally good or bad.

      Thanks for the great comment. Steve x

  • Argh this was so great! I’m currently writing a fiction piece about just this sort of person and the butting of heads with his spouse. It’s good to see I was on the right track and picked up some extra knowledge about the subject. And, of xourse, I’ll be applying this advice in my personal life. Thanks!

  • :):):)♥♥♥ Dear wonderful Hussey brothers ♥♥♥:):):)

    ♥ May I say: ♥
    With all my heart I thank you :)
    I looooooooooooooove this blog :)

    I agreeeeeeeeee :)

    Loooooooooooooooooooove LOVE ♥&♥ looooooooooooooooooove the guy with all your heart :)

    Ask him who ♥&♥ what he truly loooooooooooooooooves
    ♥ Until you know everything he looooooooooooooooves ♥ Until you know even more than him :) ♥

    I believe: If you truly LOVE a person you never get tired of loooooooooooooooooooving :)
    ♥&♥ Asking him questions of LIFE ♥&♥ TRUE LOVE :)

    Know everything he truly looooooooooooooooooves ♥&♥
    keep it deep deep deep in your heart forever :)

    ♥♥♥ Discover his heart♥♥♥
    ♥♥♥ Discover his life ♥♥♥
    ♥♥♥ Discover all his sweethearts♥♥♥
    ♥♥♥ Discover all his passions ♥♥♥
    ♥♥♥ Discover all his dreams ♥♥♥
    ♥♥♥ Discover everything wonderful ♥♥♥
    ♥♥♥ Discover all that touches his heart ♥♥♥


    I agreeeeeeeeeeeeeeeeee :)

    Tell him with all your heart that you
    ♥♥♥ Believe in him ♥♥♥

    I believe: If you pray for him with all your heart ♥&♥ you truly bealieve in him ♥&♥ his true LOVE he will always be a winner :)
    True LOVE is the strongest element :)


    Jesus said:

    “Have faith in God. For assuredly, I say to you, whoever says to this mountain, ‘Be removed and be cast into the sea,’ and does not doubt in his heart, but believes that those things he says will be done, he will have whatever he says. Therefore I say to you, whatever things you ask when you pray, believe that you receive them, and you will have them.

    “And whenever you stand praying, if you have anything against anyone, forgive him, that your Father in heaven may also forgive you your trespasses. But if you do not forgive, neither will your Father in heaven forgive your trespasses.”

    (Mark 11:22-26)

    ♥♥♥ Kiss his heart ♥♥♥
    ♥♥♥ Until you know how to kiss it in the best way ♥♥♥

    ♥&♥ May angels surround you when you kiss each other with all your heart ;)

    Oh hallelujah romance on planet earth :)

    All in all, men ♥&♥ women deserve 100% LOVE :)

    May true LOVE always surround us & be in our hearts in the best way :)

    God bless our hearts :)
    May our hearts be filled with true LOVE forever :)



    1. Awwwwwwwww :) A guy who wakes up to looooooooooooooove :)
      How about a woman waking up every morning singing
      ♥ I loooooooooooooooooooooooooove you with all my heart ♥
      If only it was possible to sing it endless times :)
      I’d always sing it for him :) ♥

    2. What Matthew & Stephen said is so so so so true :)
      Looooooooooooove it :)

      English tea for the Hussey brothers :)

  • I’ve dated extremely ambitious and successful men – and all of the following points you make are very true…though I feel the best type of women for extremely ambitious men are those who are a bit more passive, and have the time and patience to support him through his journey.

    Being an ambitious person myself (career focused workaholic and a fitness nut), I find it hard to make it work given both our temperaments and where our priorities are set in life. There is a definite attraction, but the sustainability is pretty bad. Please write a blog to help out ambitious girls like me!

    1. I think this blog is for ambitious girls like you as well! Like I said in the article, ambitious men love ambitious women – but just because you have your own priorities, he needs to feel your encouragement and support as well. He needs to feel like his success is also important to you as well as your own. It doesn’t mean you ahve to give up any of your own plans – he just needs to feel like he’s able to impress you. x

  • HELP!

    I’ve known a guy for several years through a social interest group and we’ve always gotten along well. Recently a girl friend invited me to her church, possibly because she knows I am interested in him and he goes there too.

    At the church, when we are alone, our conversations are fantastic. However whenever his male friends approach, he shuts down; refusing to make eye contact or talk to anyone.

    I get along easily with people and just introduce myself, but I’m super confused about why he does this.

    Am I doing something wrong? Sometimes his male friends flirt with me, but I act politely disinterested. It feels almost like he’s embarrassed to been seen talking to me.

    1. It sounds like it’s his problem. Give a little space and see if he initiates contact. It sounds like you’ve already shown your interest – let him reciprocate it back (after all, you want a man who is willing to do a bit of the pursuing). If he doesn’t, just treat him as a friend and carry on meeting other people.

      All the best, Steve x

  • Thank you Stephen! Your writing has helped me in partially kicking mu ex out of his pedestal. I do love him still but your point on investing because he has big plans hit me. Most of the time he just likes making plans but ner really pushes towards that. I just kept thinking maybe in a year’s time he’d finally do something and actually push through. Thank you Stephen!

    1. Thanks so much Sophi – really pleased it inspired you to take the action you need to move forward. x

    2. Sophi your comment was very interesting because your ex describes my boyfriend perfectly. He and I began dating February 2014 and Coincidently his ex-girlfriend’s name is Sophi.

  • This is a great piece Stephen! Would love to see more of you on the tours though… when you need a breath of crisp air, make a stop in Toronto. We got the chills!


    1. I am so tempted Dina. I’ll be on a couple of programmes this year, but not the tour unfortunately. I have plenty of friends in Canada though so will get there soon anyway! x

  • I love reading your posts Stephen.
    I want to emphasize don’t love him for his ambition and potential. I made this mistake with my ex-husband. He did not achieve his potential as I thought he would and at some point he burned out and changed his dreams. Being very driven myself, I went out and became successful in a way I never planed or wanted. This was disastrous for our relationship.

  • What if you are dating a very ambitious man that successfully runs his own business and he spends all his extra profit re-investing in his business and working 7 days a week? How do I support him yet handle him working as often as he does? He makes time for me, but when he does he is often exhausted and I can see he’s really trying, but emotionally he’s just drained. I really don’t know how to support him without going to the negative or asking when we can spend more time together without sounding like I’m complaining.

    1. Same here. Me and my boyfriend are struggling with our relationship right now because the priority is the business and his ambition. I am helping the business but sometimes I complain because I also had a 9hr shift on my job. I also feel exhausted sometimes. But he doesn’t like it when I’m complaining as he thinks that I’m against him.

      What do you think I could’ve done to avoid this?

      And how did you handled your situation?

  • Women don’t walk but run from guys who are super ambitious. I am a physician, stylist, musician, ballroom dancer and aspiring novelist as well as a single dad. Women take one look at my schedule and run for the hills. My female dance partners tell me that women will settle for a guy who is unemployed and sits around playing video games over a super ambitious guy who is on the go 24/7 simply because at least the video game playing guy is available to have a relationship as opposed to the super ambitious guy.

    1. Try finding single moms who are actually looking for ambitious single dads since they both are already balancing work and family. If they can prioritize being humble and appreciative, I don’t see any obstacles for their relationship.

      You can thank me later.

  • I believe a good quality woman who truly believed in herself will only look for a good quality man.
    His ambitions and lifestyle are very much a part of that.
    My life is incredibly full already.
    I have a business, two teenage daughters and a home to look after.
    I take yoga classes, dance classes and have a busy social life.
    If a good enough man came along then I would expect him to be equally as busy but would find enough time to include him in my schedule.
    A man with nothing to do…… would be my worst nightmare.
    I would not be attracted to him.

  • I had a wee taste of this last weekend, he told me about his new car he’s purchasing and that he’s looking at buying a house. This article has made me smile, maybe he’s back for the long haul this time ..

  • Seriously Stephen, you just described the relationship I have been in, but broke up (amicably) last night to a tee!

    He has been in pre-med school. Would talk to me about classes. Showed off his smarts. I did everything I could to support him. I sent motivational/ thinking of you text messages during midterms and final. I cooked for him so he would have a meal or two during the stressful weeks. All the while working on my own ambitions to start a non profit.

    Now though as he applies for med school, he cut things off. He’s likely going to have to move out of state and have 4 yrs away. I said I was willing to try long distance, but he doesn’t want to hurt either of us.

    I’m just very frustrated today. I understand his thinking. And I also really care about him and want him to succeed, but now that ambition is taking our relationship to being just friends and I have to decide what I’m doing for myself again.

  • Interesting post–I’m not specifically interested in The Ambitious Guy, but these seem like good ideas for any relationship. Nicely laid out.

    I particularly like Live For His Potential vs. Inspire Him to Do Better. It’s a delicate balance, eh? To see the guy as he is and love him that way, but also to love the part of him that wants more, without fetishizing it or getting your heart set on anything. I mean, you don’t want to be Lady Macbeth, but you don’t want to be Frank McCourt’s mother, either. (Maybe Robin Wright on House of Cards? She’s got the most ambitious man out there.)

    Seems like many of the commenters on here are responding to other less positive aspects of this idea, like what to do when he is NOT going after success to please you, or making any time for you at all, or when, as his success grows, he wants to trade you in for an upgrade… but the angle here is a cheerful one. :)

    1. Yes Emily, seems like more women have experienced the negative side of ambition! Clearly a lot of power-hungry neglectful guys out there! That’s why it’s crucial to make sure you have a guy who shows he wants to invest in a relationship just as much as his career I suppose.


      Stephen x

1 2

Leave a Reply

Your email address will not be published. Required fields are marked *

All-Time POPULAR Posts