How Do I Let Men Know I’m Not Out of Their League?


Hi Evan, I just turned 37. I am very attractive and smart and down-to-earth. I love helping people and have the biggest heart. I am a positive person and smile a lot and I can’t seem to find the right guy AT ALL. I have first dates then second dates, then the guy sees my classic Jaguar and my luxury apartment and he thinks that I am out of his league. I was told that a couple of times.

I met a handsome professor and he was a good person with a great heart but he continued to ask me over and over why I was going out with him when I could have any man that I want. I am not arrogant and sometimes try to play down my looks and the Jag. Men will say “Ooh, nice car” and I’ll say “Oh, it’s old.” Are men thinking that I am too expensive? Do they think I’m out of their league? I don’t have a league — I just want to meet a nice guy! Help… Niki


Let’s flip this over, shall we?

Good looking guy with a big heart and a fat wallet drives a Ferrari. (It’s his second car — the Jag is in the shop).

The only men you can intimidate are the WRONG men.

He goes out on a first date with you. You look at him and swoon, before asking the very serious question: “I don’t get it. Why are you single? You could have anyone.”

He says, earnestly, with a sad smile, “I just haven’t met the right girl.”

You reply, “I get that, but how can I possibly trust you? You’re 37. You’ve probably been with a hundred women. And from everything I’ve experienced, guys like you aren’t solid relationship bets. You’re a lifetime bachelor with looks and money. You’re an alpha male with testosterone and ego. My dating coach told me to run from guys like you and stick with nice guys who want commitment.”

He says, “I am a nice guy — who just happens to be successful. I am very much looking for a wife and family. You can’t judge a book by its cover.”

I don’t know about you, Niki, but I’m sold.

And any guy who chooses to engage you beyond your looks and car will be sold on you as well.

As I’ve said repeatedly, the only men you can intimidate are the WRONG men.

A guy who feels the need to run away because he can’t handle your beauty, success or kindheartedness is nothing but an unfortunate and pathetic little man.

Good riddance to men who are afraid of Ferraris or perfect bodies or PhDs.

They don’t even count in my world.

If you are as great as you say you are, you should have no shortage of quality suitors.

I guess the only question I could ask you is the same question I’d ask of any man who perpetually finds that women are “intimidated” by him: How come you’re letting people get intimidated by you? Why aren’t they seeing your friendly, open, warm, vulnerable side?

If you were a comedian, at a certain point, you can’t keep insisting that you’re funny but “nobody gets the joke”.

As a single person, at a certain point, you can’t keep insisting that “all men” are intimidated by you, no more than a woman who suggests that all men are liars, players, losers or perverts.

It’s easy for you to sit back and say, “I’m great, but no one can handle me.”

It’s harder — and more important — for you to look in the mirror and figure out why.

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  1. 1

    Niki – I met a very nice lady who had a similar complaint – she felt as though men were intimidated by her wealth. I explained that her profile certainly gave many hints of her wealth – pictures of her sailing in the Med, mention of her beach house, her part-time employment in an art gallery, etc. To cap it off she drove her Porsche for our first dinner.

    I explained that men are going to fall into one of three basic groups: 1. those who are intimidated by a wealthy woman; 2. those who are going to view a wealthy woman as a potential “sugar momma”; or 3. those who are not going to be intimidated whatsoever.

    My advice was to downplay her wealth & revise her profile; run from slackers looking for a sugar momma; and focus on men who are not going to be intimidated (primarily other high-earners).

    Telling a wonderful man who is 5′ 4″ that women who aren’t interested in him are not worth his time or energy isn’t very helpful. There’s a very lengthy blog that discusses the reality that it is more difficult for short men to find a GF. Likewise, many men are going to be intimidated by a woman who is extremely attractive and appears to be wealthy. Is it fair? No, but it is the reality. (Read some of the comments on “Why Don’t Men Like Smart, Strong Successful Women” and “Pity the Pretty”).

    You are in an enviable position in many regards. While some men will always be intimidated by you, you can overcome the initial feelings of intimidation that other men may have by your words and actions — make the man realize that you are truly interested in him for who he is — and the initial feelings of intimidation and uncertainty will soon dissipate.

  2. 2

    yeah, there’s a piece missing from this puzzle…I’m a 42 year old guy and I don’t know any guys (but I’m sure they exist in some form) who would not go out with a hot woman with a nice car and nice place… it’s not the car or the apt., it’s something else, trust me

  3. 3


    People who might (wrongfully or correctly) eliminate a person based on something superficial, would not eliminate that same person if they already knew that person a little bit.

    Why not give these guys a chance to know you by leaving the Jaguar at home for several dates?


  4. 4

    Rachael Greenwald covered this exact problem in her book “Have Him at Hello: Confessions from 1,000 Guys About What Makes Them Fall in Love . . . Or Never Call Back”.
    It’s what she called “The Park Avenue Princess” problem.
    If men think that you’re high-maintenance / “expensive” – i.e. they can’t afford you financially, or don’t think they have anything to offer you – they will back off, no matter how lovely and charming you are.

    In my experience, cars are one thing that guys do notice immediately. They may not know how expensive your dress / shoes / handbag is, but they know exactly how expensive your car is.
    Don’t drive the Jag to your first few dates with some one new – take a cab.
    Let them see the real you minus the heavy bling (expensive car, flashy jewelry). That’s not to say that you must dress like a schlump. Just tone it down a wee bit.

    Find a way to work into the conversation what it is about the guy that you find attractive / awesome / admirable that has nothing to do with money / wealth, and ideally is something unique to the guy.

    Then he will feel appreciated & admired for himself (not his checkbook) = good ego boost = he won’t be intimidated.

  5. 5


    How can you be sure it is something else? I am a lawyer, and I was dating another lawyer years ago. I made partner at my firm. I did not discuss the huge salary increase, but most people in our area know the firm well-and the large salaries that come with partner status. My ex worked as a public defender. We were having dinner one night, and he advised me that he did not want to date a woman who earned more money than he did. Mind you, I NEVER discussed income, bank accounts, or anything else financial with this man. I tried to laugh it off by saying, well, there is simply more to donate to charity. He then advised that he wanted a woman who was the “setting” (for a ring), not the entire “ring” by herself. I never flaunted my success. I always stroked his ego. Of course, we broke up that night. Years later, I am dating a teacher who loves me and just went ring shopping with me. I know he does not have a large salary, and I am fine with that. I picked a classic ring that reminds me of the first ring my father gave my mother when they married years ago. My teacher is a far better man than the 5′ 5″ attorney who suffered from very low self-esteem. He constantly referred to himself as “ugly”. I tried to convince him otherwise. What a waste of time. Some men just don’t understand.

    1. 5.1
      Jenny Ravelo

      And you just proved David’s point by saying you managed to find a good man. There are men that are gonna be intimidated, that’s true, but when it becomes a pattern, something else is under the waters. Maybe she comes off as pretentious when she shows them her car, or maybe she unconsciously goes after insecure men.

    2. 5.2
      Erik V

      May I point out that the teacher may have a much higher impact on society than any lawyer because the molds his students, instills values and morals, … while lawyers only have a marginal impact on the society.

      My father was a teacher and it did happen frequently while being somewhere we walked into one of his old students, he was proud that he did did contribute to the life of his student and the impact he had.

      I just used another standard, i.e. a basis for comparison, in which the man is ahead of the woman. But I have to admit such a thing can only be done if the man has high self-esteem.

      There is a famous couple in the United States, she was one of the best lawyers in her city, the capital of a small state,  he was a local politician, she made much more than he   could ever dream of, then he became the 42th president of the United States.

  6. 6


    If Niki will let me drive the Jag
    please give her my cell number.

    All best wishes,


  7. 7

    “They may not know how expensive your dress / shoes / handbag is, but they know exactly how expensive your car is.”

    haha Robyn, soooo true!

    Rachel Greenwald’s book is one of my favorite dating books and every single woman should get their hands on it.

    It’s one of those rare dating books that are actually based on raw data.

  8. 8

    Robyn hit the nail on the head. Unless they’re wealthy themselves, guys will look at you and think, “I’m not going to be able to afford to keep this woman in the style to which she’s become accustomed; why bother getting to know her?” If you’re well-off, you gotta be low-key about it.

  9. 9

    I feel for you Niki but my past experience in dating (prior to my marriage) leads me to believe David is more accurate. In fact, it was a date with a highly successful, attractive woman that led me to realize that my wife to be, was the girl for me. In short, she spent the entire date talking about her career and her travel, that she was never at home. It became clear to me that she wasn’t being honest with herself that she wanted to ‘settle down’. To this day, as far as I know, she still hasn’t and it’s three years later.

    If you really want a nice guy who’ll treat you well and his status doesn’t matter, they’re not so hard to find. I don’t think a good man runs from the superficial qualities of looks and wealth, they run from red flags, particularly when they know what they want. But I think as Evan said, look in the mirror first, make sure what it is you really want, and then be open to the types of guys you say you want.

  10. 10

    This is another of those interesting scenarios where the men appear to be divided in how they think. Some men commenting here (and in Rachael Greenwald’s book) would not be comfortable dating a wealthy woman, because he would fear that he couldn’t provide for her. Other men such as Carl and david wouldn’t mind at all.

    Perhaps this is one of the ways of thinking that needs to change with time. As women on average gain parity with men in terms of income, there will be a growing number of women who are substantially wealthier than many men, just looking at distributions. That doesn’t mean that they don’t want men, or feel that the men need to subsidize them!

    Men, there are many ways that you provide for women and make us happy that have nothing to do with consumer purchases. If women don’t mind, why would you?

    1. 10.1
      Evan Marc Katz

      It says far more about the men than it does the women. And since you can’t change men, as a woman, all you can do is a) realize that your target audience is men who are NOT intimidated by you, and to b) become self-aware about any off-putting behaviors that may unintentionally sabotage your success.

  11. 11

    Well, this is how I see it. We fall for someone not so much based on what we think of them, but how they make us feel about ourselves. (Or would it be better for me to say how we find ourselves feeling about ourselves due to them.) It’s great that the woman is smart, pretty, and kind, but does she make ME feel uniquely smart and cool.

    I am wondering if the guys that Niki has been seeing have any idea of what she likes about them. This actually is more important that someone like Niki, who has all this going for her, shows this kind of appreciation to the guys she is seeing, than it would be for a plainer woman to show that kind of appreciation to the guys she is seeing.

    Why? Well the best way I can illustrate it is to point out that employers shy away from hiring what are known as “overqualified” candidates. It’s not so much about the employers being “insecure”, they just know that hiring someone overqualified might sound great in theory but, going by how similar-looking situations have worked out in the past, is actually a bad risk for them. The way the employer sees it, the overqualified candidate might not work as hard or she might leave when a more suitable position comes up. It’s just how these things tend to play out. So if the overqualified candidate really wants to be hired, has to work harder to show the potential employer that she really wants this job and why.

  12. 12

    @Niki #5
    Driving a Jaguar is not flaunting success?

    Ever hear of the book “The Millionaire Next Door”? Their favorite cars were Corollas or Camry’s. LOL, maybe you can get that rich and get more dates by leaving the Jag at home? 🙂

    No disrespect


  13. 13

    In reply to #10 and #11

    Helen: not all men are the same. Just like some women don’t care about money, some do. We are individuals.

    Why should men change? If there was an article about something that made many women uncomfortable or feel unfeminine everyone would be supportive at least to the point of telling them “well that is what you are about, that is fine”.

    Why not with men who don’t feel comfortable dating a woman who makes much much more than them?

  14. 14

    All of us want to be “needed.” For men, as Michael said, smart, pretty, and kind is great, but unless a man feels “needed” it doesn’t go far. I am an attorney, I make a decent living and get to do stuff I really enjoy. But let me tell you, I am not driving a Jag (own a SUV that is a Hybrid), wearing my rolex, expensive accessories, or telling my potential date about my beach house, my speaking engagements or the daily battles at work. Instead, I lead with my hobbies, if he asks, volunteering, cooking, photography, and every month I take a small road trip in CA to run a 1/2 marathon. I have had a date think I am a paralegal for two dinners, just because I didn’t talk about my profession (I avoid it at all costs). On the other hand, I want to be provided for and protected–so my dating pool at my income and age is rather small (I am fairly young-don’t worry very optimistic too). And I can see that once they realize what I do, see my home, this gets complicated. “Google” doesn’t help! I have heard, “why do you like me,” and “so where would I fit into all this.” However, I think this has more to do with the men she is selecting and what she is leading with.

  15. 15

    Michael17: I know you always tell it exactly how you see it, so thanks. This is helpful.

    Steve: note that I never stated explicitly that it’s men who should change. I think society as a whole – both men and women – will be changing how we think about men, women, and money in the future, as the income disparity narrows. There are possible implications for many ways in which men and women interact. It is an interesting time.

    Niki (OP): I think some of the points people here have raised (Michael17 and Still Looking) about making your special man feel special would be helpful for you. He wants to know he has the ability to provide you happiness and satisfaction in some way.

  16. 16

    @ Steve #14: well I’ve dated single dads. Fifty years ago, there was no such thing, just as there was no such thing as a high-earning woman. Times change, and we have to adjust, otherwise we will end up eliminating a lot of good people for no valid reason.

    Michael17 has some really great points in #12, IMO. They apply not just to Niki, but to any woman that has a lot going for her. Or man, for that matter.

    One more thing — to the commenters that tell Niki not to “flaunt the Jag” — her letter actually says “I have first dates then second dates, then the guy sees my classic Jaguar and my luxury apartment and he thinks that I am out of his league.” So it looks like Niki isn’t necessarily flaunting anything, it’s just that, she cannot hide her apartment and her Jag forever. What’s she supposed to do — lie about it? tell him, “Oh no we can’t go to my place today, my six roommates are home!” Sooner or later, he’ll come by her apartment and see the Jag! What do you recommend?

    1. 16.1

      public transit?


      I’ve experienced the same thing driving my Audi A7.      I conducted an experiment and kept the car hidden until date number 5.      Audi was an instant emasculating machine – smile was gone from his face – and the rest of him followed.    Haha

  17. 17

    The Jag would make me pause, no doubt. Especially if I see it on a first date. I don’t think that pause is a sign of intimidation. It’s more that I’d wonder if I would be able to keep up financially in any way to what this woman is used to in terms of dating. This would especially be the case if I didn’t know her at all, and only had what was present to base any judgments on.

    I really like Helen’s comments here (that might make a few laugh, given how contentious we were with each other on a recent thread.)

    “Men, there are many ways that you provide for women and make us happy that have nothing to do with consumer purchases. If women don’t mind, why would you?” This has always been my approach to dating. Not being fixated on how much money either of us spends, and seeking women who are also not fixated on that, and who see that there are so many other ways to show you care.

    The thing is, you don’t really know how someone operates until you spend some time with them. You can find people who makes little money but expect high class everything on dates, and you can find people who are well off, but are totally flexible about dating, money, and the rest.

    So, maybe Niki just needs to figure out a few ways she can demonstrate that flexibility. To show guys she isn’t expecting that he break the bank to date her. And yes, I’d agree with the others that if you can leave the car home for awhile, do so.

    1. 17.1


      I disagree; the only men Niki (or any other woman,) can “intimidate” that way, are the ones who need her to be less than she is, so they can feel like more than they are.   That is their problem, NOT hers. A man totally secure and comfortable with who he is, and what he’s done, doesn’t need to do that, because he has nothing to “prove”. There ARE guys like that, usually pretty successful, and pretty much alpha in temperament; it takes a pretty strong personality to handle that kind of success, whether it’s your own, your partner’s or both.


      1. 17.1.1

        First, alphas doesn’t require looks or wealth, they’re alphas people value their leadership. A priest can be an alpha, D.A. Second, you just pointed out that only a successful man would be able to handle her success-suggesting that a man must match her earning power. This is just dumb. She’s a lawyer, not a princess. The man just needs a job and be a good guy all around.

        I’m not intimidated by high-earning women or men, beauty, or any other superficial nonsense. It’s usually women’s fear of judgement that keeps them from dating a poor man, or a short man, or any of the other crap I keep reading about.

        Moreover, women just hate admitting to being like this because, again, the perception of others matters more than anything else. They’ll hide behind all kinds of excuses like “men are intimidated.”

        I can tell you right now, if she’s using online dating, being a female lawyer is the kiss of death. There are so many above average height, entrepreneurial, or high-earner women online who for some reason think their accomplishments and stats matter at all to men, and keep shooting for the tallest, wealthiest, most educated dudes that are just swimming in 23-year-old women. Those men will NEVER choose a post-wall woman who is use to pampering herself with material things. They eventually settle down with a hot, struggling barista because he may finally want to leave legacy and she’d happily volunteer for the taste of the good life and the high potential for successful kids.

        Lady, stop blaming men for not seeing what a catch   you are, and just go live your life. Find some friends.

        Btw, if all of your friends are married, you did it wrong.

    2. 17.2

      I know how to “tone” it down, because I was guilt-tripped my whole life by relatives and others who felt bad because we had more. I was born into it and I was given nice things and a fine education. Am I supposed to turn these privileges down?

      All my life people made an issue about my privileges.  They shamed me. They asked countless questions. They kept harping about how fancy my dress, bags, shoes, etc. were. “I don’t know how you can afford that.” Even when I’m not wearing the nice things, they still find something to fixate on. “Is your dad rich?” “How much is your allowance?”

      How to tone it down:

      Not wear jewelry.

      Not drive expensive cars.

      Not mention about assets and properties until they grill me.

      As soon as I mention I have that stuff, they get disappointed or they feel bad about themselves. I realized, it’s THEIR problem. They have issues.

      As for dating – I figured I will only date people who aren’t intimidated and can hold their own or those who already own and enjoy the same things.

      It sure limits the pool but I wouldn’t have it any other way.

      I used to “tone” it down and realized I wasn’t being myself, while the people who expected me to “tone” it down weren’t making concessions for me at all. I was dressing down (I love to dress up). I went to cheap restaurants for their sake. I sat around in parks and just chatted with them because some of them couldn’t even afford a cup of coffee. I would go to matinees instead of evening shows because they needed to save a couple of dollars. I would take a taxi and some people complained that I waste money. I was flexible and understanding and it didn’t necessarily get me the relationships I wanted.

      But I’m not going to spend the rest of my life apologizing for my lifestyle. It’s what I prefer and I want to be with someone who can enjoy the same things. No BS, no guilt-tripping.

  18. 18

    You know what? I’d be freaked out by a MAN with a jag, too! I would find it materialistic and off-putting; I’d wonder why the guy wasn’t spending money more wisely and question whether our values meshed. I’d wonder if he would try to buy my affection. I make plenty of money for a single person and grew up in a six figure household but we saved our money for a great college education and travel, not to throw around on a huge fancy house and fast cars.

    There is nothing wrong with that lifestyle, it’s just difficult for me and probably many others to comprehend — because I’m not in the same class and league. It seems that there are often problems when trying to date above or below one’s league in looks, education, and social status. All this advice about finding some bald, nerdy nice guy to date doesn’t exactly work unless you are nerdy and average yourself. I rarely get pursued or asked for a second date by a guy less attractive, educated, and successful than me– and I think at the end of the day, a mechanic who grew up in a blue collar hood will want a similar woman because that’s who he’s COMFORTABLE with. Who he’s compatible with.

    Maybe this woman should work harder to find men closer to her status, or who share her values — say, a guy who may not make a lot right now but is excited about starting his own business and can see himself caring about nice things.

  19. 19
    David T

    @David 2 I think it could be many things and it is going to be different from man to man.

    Sometimes it is an ego thing. Some men just don’t feel “manly” enough if she makes more. (Nikki’s 5’s public defender is an example. Also comparing a person to a ring is disturbing so it just as well he didn’t like the money situation.) That is silliness, IMO. In some men’s cases it might be a self-esteem “I can’t afford her” thing (Nathan 18), thinking “I won’t be able to keep up with her travel, fancy restaurants, etc. She won’t want me simply for who I am and be willing to help pay my way.” I think many men fall in here.

    In other cases it can be a more fundamental problem of mismatch values. For context, a few years ago I dated a well off lawyer who made about 4 times my already fairly generous salary. It was a bonus that she was so well set financially. She lived in a nice but modest house and drove a mid-range SUV (just like Liz 15), but she could have afforded much more. We were gf/bf for a few months and parted amicably for reasons other than money.

    Recently I briefly considered dating a nice woman (we went out once) who was independently wealthy. She had a few issues that made her unappealing to me, but the first deal breaker was what she drove, how she dressed, her manicure, her bling, etc. . My problem wasn’t that she happened to have enough money to own whatever caught her eye but that she put real value in having expensive things. That was clearly important to her.

    Mia hit my number on the values (though I disagree about the class and league thing. If values match, it becomes a choice whether or not to feel comfortable.) No matter how much money I make, I will never own a Jag or Porsche or Ferrari or Maserati etc. because that is not what is important to me. If I had the extra money, I *might* go to the expense of having my shirts fitted so I look nice, but I am not going to spend $500 on a pair of jeans, or $800 on a shirt just because it has a fancy brand name that also happens to be high quality. That is a real turn off. Like Nikki 5 said, for me extra money means more for charity.

    It is a choice and whatever floats your boat is fine. If I dated the OP, every time I saw that $200k 1966 Jag and sat on her $15,000 antique divan looking at her wall full of $22,000 Theodore Geisel prints, I would be thinking about what else could have been done with that money, and it Don’t Work For Me.

  20. 20

    Having known quite a few professors, I could see how a man like that could not be all that compatible with Niki. They don’t make tons of money, they tend to be very involved in their intellectual pursuits, and relatively non-materialistic, as a general rule. I agree with Still-Looking (#1), that her best bet would be men with similar values, and a similar earning capacity.

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