Why It’s So Hard to Meet the Right Guy

As a dating coach for smart, strong, successful women, I understand how hard it is for you. You go online and you swipe through thousands of guys. The guys you’re not attracted to pursue you hard. The guys you like the most are wildly inconsistent and don’t follow through. You have moments of despair, wondering what’s wrong with you, why is this so difficult, and whether you’re ever going to meet a guy to get you off this dating treadmill. Today, I’m going to teach you how to persevere when the going gets tough and how to guarantee you’ll meet your Mr. Right.

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  1. 1

    I’m 39 years old. No kids. Wealthy. Retired. Never married. Women age 30 and older bring too much mental, parental, and financial baggage and that’s why they can’t get a high quality man because high quality men their age dont want them. So I stick to childless physically fit fun acting women age 20 to 25.

  2. 2

    Hi, Alexander, thanks for your post. I can definitely see where you’re coming from.

    But when it comes to dating, I would urge you to open your mind and relax your standards. Often the best gifts come to us in the strangest (or most unexpected) of packages. On this blog, Evan has been great at pointing that out, and providing accounts of women who have used his guidance to find the love they always wanted.

    I am 39. No kids. Never been married (or engaged). I have no, as you say, “mental, parental, and financial” baggage. I am, however, a well-adjusted woman who has lived a very full life (much more to come!). I have a wealth of experiences that have made me into the happy, successful, intelligent, and enlightened person I am today. I could not say this when I was 20-25.

    I’m 5’8 and weigh 135lbs. I’m often told I look fifteen years younger than I really am. Many times I’ve been asked if I am a model (I am not. Though it’s a flattering compliment, I was never interested in that).

    I’ve always been very active. When I was younger, I was an elite athlete. While I can no longer do what I could in my athlete days, I’m proud that I can still deadlift almost 300lbs, squat 225 lbs, and can run a 6-minute mile. I can also do the splits 😉

    I have driven myself to excel in other areas of my life. I worked very, very hard to earn my PhD from one of the top three universities in England (I’m an American). My doctorate allows me to have a career that I dearly love, and one that provides generous financial security. I will never have to rely on anyone to take care of me.

    In my free time, I pursue all of the usual hobbies, plus new ones that I’m adding all the time as I try new things and have new experiences. Many of them I find through traveling, which allows me to meet new people and practice my foreign language skills. I’m determined to become a polyglot by the time I’m 50 😉

    I’m very happy and content with my life. My days are full of meaning, love, and a lot of laughter. I have a ton of stuff going on, and am always learning something new. Andespite the devastation from the pandemic this past year, I am optimistic that brighter days are ahead.

    If I meet a guy who can be a true partner to me, and who I want to settle down with, great. But if that doesn’t happen, that’s fine, too. I’m not standing still, and I’ll be loving life regardless. Especially when I have wonderful friends all over the world that keep things interesting!

    It’s worth mentioning that many of my female friends are also childless, in their late 30s-early 40s, are just as accomplished and positive-minded as I am, and are also very happy with their lives. We are mature, kind, hard-working, ambitious, and highly intelligent women (and yes, we’re also attractive). In short, we’re “good people.” And we’re certainly not worried about men not wanting us (especially men that make arbitrary assumptions about “quality.”).

    Again, I get where you’re coming from, Alexander. Dating can be so frustrating and disappointing. Especially if all you want is for the madness to stop, and to find the right partner so that you can move on to the next iteration of your goals and dreams.

    But I have to say, and I mean this in the kindest way possible – I would never consider dating a man with your mindset. Neither would any woman I know.

    By overgeneralizing based on a tiny sample size (your own), and going a bit too heavy on the condescension, I think you’re really limiting yourself. And by allowing your dating choices to conform to an overhyped stereotype, you are missing out. Not just in terms of meeting women. But also in terms of what becomes possible once we set aside our own unexamined assumptions about how we think it has to be.

    Just my two cents. Best wishes to you.

  3. 3
    In Hiding


    IMHO, it’s best to leave well enough alone when it comes to guys like Alexander. What he calls “baggage” might just be women who don’t put up with nonsense.

  4. 4


    Based on how you described yourself you’re the “very small”(10% give or take) minority of women age 30 and older. I’m just looking for women who’s gainfully employed and financially self sufficient( I don’t care if she has a college degree or not or what type of job she has), physically fit and pretty in the face, no kids, she’s fun to be around and she actually have plenty of time and energy outside of work to do fun things . I can “easily” find this type of woman between the age of 20 to 25. It’s extremely hard to find this type of woman age 30 and older. And any woman turned off by my attitude, no hard feelings. I’m not trying to impress all women.

  5. 5

    @Alexander, the type of women you describe in the 30+ range is not typical or accurate. The majority are educated, sane, physically fit, attractive, confident and worked out all their hangups and insecurities they had in their 20’s. It’s the best of both worlds; you are still hot, and you are making more money and worked through all your crap. It’s actually the best age for what you are looking for. The vibe I am picking up from your response is there is something about YOU that attracts the crazy ones….strong, confident, sexy, wealthy men attract all types for obvious reasons, you are at the top of the food chain. If your experience is all women over 30 have issues, you might want to reevaluate why are not attracting the top 10% of the 30+ sect? They are not coming around Alexander…might want to explore that.

  6. 6

    I never said I “only” attract women age 30 and older who are crazy. I’ve met a “few” high quality women age 30 and older who measured up to most of my dating requirements. And a top 10% quality woman age 20 to 25 to me is still a better compatible deal for me than a top 10% age 30 and older woman. Also, I keep seeing women posting comments about their income status, type of job they have, and college level education- a woman’s income level, job, and college degree doesn’t give me a hard on. A woman with no college degree making 50k per year and she doesn’t need financial help from anyone is of “equal financial value” to me compared to a woman with a college degree or no college degree making 100k, 500k, or even 1 million dollars per year who doesn’t need financial help from anyone. As long as a woman isn’t overweight, has a slim physically tone body, petty face, no kids, dont need me financially, has common sense, feminine acting, highly trustworthy, mentally healthy, isn’t an alcoholic and doesn’t use drugs , isn’t bitter towards masculinity and expect a man to take charge, I dont care about anything else.

  7. 7
    Emily, to

    I’m curious what you bring to the table for these young women who are in their prime and can get anyone they want. Younger women usually go out with older men because they are more stable financially and offer commitment. You write you are wealthy but you want the woman to be financially independent. And it doesn’t sound like you want a long-term commitment. Twenty-five year-old women go out with 25-year-old guys .. because they can. I would if I were that age, too.

  8. 8


    I offer them fun and new experiences they never experienced before. The vast majority of men their age are weak, emasculated, indecisive and inexperience(their words, not mine) . And no I’m not looking for a committed relationship, just sex and fun outings and they know it and are ok with it.

  9. 9
    Emily, to

    But you wrote you don’t want a woman who expects the man to take charge, so I’m not sure how you can call younger men indecisive.
    If a young woman wants fun and just sex, she’ll date a man her own age. A guy who is 15+ years older feels like her dad. He’s in a whole other phase of life she has no interest in knowing about, particularly if she’s still in college, where she’s going to have the largest pool of available men her own age she’ll ever find. That also tends to be true of up to about mid-20s, when a good number of still-single young people are hanging out at the bars and clubs. A woman has so many options at that age. There’d be no reason to go older. Unless, as I pointed out, she wanted someone who would take care of her financially or offered commitment in a way the guys her own age weren’t, and that is probably something she’s thinking about in her late 20s. Johnny Depp was 40 when he did the first Pirates movie, and aside from his looks at the time, he also exuded an I’m-my-own-person cool. A guy like that, yes, would have no trouble attracting much younger women, but I personally don’t know any 40-year-olds like that; they all have an air of responsibility about them.

  10. 10


    Dont put words in my mouth- I never stated I dont want a woman who expect men to take charge. The type of women I get romantically/sexually involved with are only attracted to men who take charge. And if beautiful women 10 plus years younger than me didnt find me physically and emotionally attractive they wouldn’t get with me – period. Also, I dont advertise my wealth to female strangers I’m interested in. I rely on my physique, charm, and communication skills to get beautiful women upfront. I let them on their own terms find out I’m wealthy as they get to know me more and more the first few weeks.

    Again, if young beautiful women in their early 20’s found a 39 year old man like me physically, sexually, and emotionally unattractive, a 39 year old man like me who make it clear to them upfront I’m not looking for commitment,
    just sex and fun outings, they wouldn’t have sex and spend time with me. Period.

  11. 11

    I’ve met plenty of fit, attractive, and cool men in their late thirties and early forties who are perfectly able to attract and date pretty women in their late twenties. You’re really generalizing with your comments in terms of what women that age might want.

    In fact, you sound like a 50+ woman who is a little resentful that she can no longer attract the type of men in her age range that she wants most.

  12. 12

    @Alexander: No quarrels with what you want, I’m just impressed that you can find a “gainfully employed and financially self sufficient…woman between the age of 20 to 25”. In my area, the cost of living is such that few single men OR women are truly financially self-sufficient at such a young age. Most are still highly dependent on their parents to maintain their desired lifestyle.

  13. 13
    In Hiding

    I don’t know who these women are that spend their time bemoaning not being able to attract men their own age. We’re smart enough to know that we don’t have any control over someone else’s preferences, so why should we internalize and think something is wrong with us because we don’t live up to those preferences. It’s a waste of energy. There will always be someone thinner, younger, prettier, etc. So what? I can’t be them anyway.

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