Pity the Pretty: An Ode to Attractive Women Who Can’t Find Boyfriends

Pity the Pretty: An Ode to Attractive Women Who Can't Find Boyfriends

Dear Evan,

I am 25 years old and have never been in a serious relationship.   I am a very attractive girl and I tend to meet guys easily and go on dates mostly every weekend. My problem is that it never leads to anything more than that. I don’t know what I’m doing wrong, but the date will go really well and things tend to either move really slow, I won’t hear from them after our date for a week or so, or not at all.   My friends all have boyfriends, and I’m really looking to settle down.   Can you help me?   By the way, it never gets farther than kissing with me.   I realize that if they don’t stick around because I won’t have sex with them, then at least I know. It just seems that’s all they are looking for. It seems that attractive girls only get guys that want to sleep with them.

Why can’t I meet a guy who sees me as more?


Dear Ashley,

Today, I’m going to take a controversial stance. I’m going heap some sympathy on the pretty girl.

Does the pretty girl have the same issues as the fat girl? No. The pretty girl never lacks for attention. Heads turn when she walks into the room. Men leap to attention and whisper to each other before approaching. Yes, the pretty girl has more dates than she needs and probably has a waiting list a mile long. What could possibly be wrong with this scenario?

By being singled out for being attractive, you’re never, ever considered “normal.”

Well, if you’re a pretty girl or you know a pretty girl, you know exactly what’s wrong.

You’re an object to men.

You never know why someone likes you.

You can be intimidating without trying.

You can come across as aloof even if you’re just shy.

You’re instantly hated by a lot of other women.

You’re assumed to be dumb by many men.

You may be insecure, but people have trouble believing it.

You’re given things by men for no reason (Free dinners! Vacations! No speeding tickets!), which creates an odd power dynamic.

You’re catered to so frequently that you may lack some kindness, empathy or social grace. When you’re constantly put on a pedestal, it’s hard to be in sync with “normal” people. This is the same thing that afflicts celebrities, by the way. Except they get to claim “diva” status. You’re just known as a bitch.

That last one is just my observation about beautiful people and doesn’t necessarily apply to you. But the point is, by being singled out for being attractive, you’re never, ever considered “normal”…

As a result, you become a lifelong target–a trophy for men to bag. And make no mistake about it, most men want to bag you. For anyone to deny this is patently foolish. I’m as sensitive a guy as you’re going to find in terms of how I communicate with women, but I can still remember the rush of dating a Perfect 10. It was as if her magical glow rubbed off on me in some way when she walked into a room. And if I can be seduced by physical attraction, and the glory that comes with landing such a specimen, I would have to assume that 95% of the red-blooded, conscience-free men would feel the same way.

Put it this way–when I was single, if I had a chance to sleep with…I don’t know…who is the most distasteful female celebrity? Paris Hilton, maybe? Yeah, I’d do it. Just to be able to say I did. I wouldn’t want to have to make pillow talk, or cook her breakfast, or call her the following day. I just want to have the meaningless experience and cheap thrill that comes along with sex with a celebrity.

Men are to pretty girls what paparazzi are to celebrities. Their constant validation makes them feel important. Their ulterior motives make them feel used and disposable.

To me, that’s the perfect metaphor–very attractive women ARE celebrities. They get lavished with attention and praise. They get perks just for being pretty. Their mere presence makes people excited, nervous, fearful, giddy. And while it might seem like a great ride being a celebrity, tell that to poor Britney. Or Mariah. Or any of the people who crumble from the pressure and attention foisted upon them.

Men are to pretty girls what paparazzi are to celebrities. Their constant validation makes them feel important. Their ulterior motives make them feel used and disposable.

I know I’ve gone on a bit of a tangent here, Ashley, because it’s very rare that we hear that the root of someone’s problems stems from being too attractive, but I believe that is the case.

Some of the most attractive women I know in Los Angeles–tall blondes with thin waists and big boobs–are 40 and single, because nice guys don’t approach them and slimy guys are always on the make.

What’s really difficult for pretty girls is trying to assess when a guy IS sincere. I mean, it’s tough enough for an average woman to tell when a guy is interested in a relationship or sex. Imagine what it’s like when you’re objectified wherever you go. You start to mistrust everybody. You make nice guys pay for the sins of bad guys. And you think that if you insist on not doing any more than kissing that you’re weeding out the “wrong” guys. You may also be weeding out some decent guys. Although it’s unpopular to say, sex is rightfully important to men. A reasonable man with looks and money and life experience might very well say to himself, after five dates with nothing more than a kiss, “Screw this. I’m going to find a woman who matches my passion, who makes me feel attractive and sexy, who is excited about me.”

It’s not that you’re wrong for attempting to protect yourself, Ashley. It’s that your layers of protection may be having an unintended side effect–putting off otherwise well-meaning men who don’t want to feel like they’re in seventh grade all over again.

So how do you decide if a man is interested in you or interested in sex? Well, there’s this previous blog post that discusses this phenomenon. And I’m delighted to report that I actually have a five minute VIDEO that takes on the same topic. Enjoy.

Despite your very accurate concerns that men want to sleep with the pretty girl, pretty girls get married ALL THE TIME. You want to know how? They let down their guard, they take a chance, and they TRUST. That would be my advice to you as well.

Good luck.

Are you also an attractive woman who can never tell if a man is interested in you as a trophy or as a human being? If so, I understand your predicament and can help you in your quest for true love.

Click below to learn more about what it’s like to have a male dating coach who can help you find the quality men in a sea of shallow and disappointing ones.



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  1. 41

    Just my experience, I went out with this really HB for lunch. During the meal, at least 3 or 4 times I found she was checking out the guys who were walking in and out. It was a major turn off and I never took her out again even though she was interested in me.
    I would never do something like that even with a woman I had no interest in.

    1. 41.1

      hey D – wanted to say what a gentleman you are! I’ve been unfortunate enough to have dated two guys in the past who did this, and it pissed me off. They both resorted to saying I have extreme jealousy and insecurities. What a major turn off.  

      To hesr a guy go through this is quite thrilling to me also.   

  2. 42

    “If she can’t put a can in a different bucket how am I going to get her to buy recycled products that typically cost more?”

    Sounds like she wasn’t the type of woman who wanted a man ‘to get her to do things’. Good for you for bailing out before wasting anyone’s time.

  3. 43

    Markus wrote:
    If she can’t put a can in a different bucket how am I going to get her to buy recycled products that typically cost more?

    If you she isn’t interested enough in your values to put a can in a different bucket you can only imagine how difficult things will be on major issues.

  4. 44

    to Brian,

    Men in their prime, do they really want to genuinely connect and have something interesting to talk about that will carry them a lifetime?

  5. 45

    I agree with Kristina, attractive women find partners, as soon as they rid themselves of what some women call the “Cinderella Complex”….

  6. 46

    I had to respond to this. My response will be educational and will give you some insights into your future as a “pretty woman”. I was once, many, many years ago, considered pretty. I am now 54 years old, have a few grays, raised two children to adulthood who are now as old, if not older, than most of you here.
    Your looks will not last forever. You need to think “as if” you no longer had those looks, and consider the men in your lives as lifelong companions who will accept you when you are pregnant and not so pretty over the toilet puking, when you are post baby with a wrinkled tummy and a wide behind, and when you pass through menopause with gray hair and saggy everything.
    Will he still be there for you? Or will he be still eye-ing women who are young and pretty and asking for their phone numbers? Will he be looking in the mirror at his own recessed hairline, or will he be getting hair transplants and face lifts so that he can find yet another young thing on the side?
    Will he be a good father, or one who never has time for his children because he is too self obsessed? Will he be so busy working that he doesn’t remember your name? Take a look at this person who you are dating with an eye towards your future and eliminate the superficial stuff, you don’t have all the time in the world to spend on playing around with time wasters. You know inherently who they are, you have the judgment in you whether you want to admit to it or not. If you don’t want to be a committed person in a relationship, then you can have all the fun you want with men who only want to date pretty women, and you can focus on your career and being an independent single woman for the rest of your life.
    There is nothing wrong with that. No one says you have to be married or be in a relationship, or even DATE if you don’t feel like it.
    I’ve been divorced for 21 years, been there, done that, had several relationships, and now, it’s a peaceful place where I don’t have to deal with the advances of men who only want pretty women. It’s easy now! If a man was interested in me now, he would probably be looking to hook up with a woman who could take care of him, and being a Nurse, I don’t want to have that happen!LOL!

  7. 47

    to ocdgirl2000

    I have heard women say what you just said. But, there has to be a fun way of dealing with this part of life.

  8. 48

    To D,

    Women have a sophisticated defense system, she may have had other reasons for checking out men.

  9. 49

    Notably, some of us have chosen to remain single simply because we are narcissists ourselves. We tend to start our sentences with the words “I” “Me” and “my”, these words are used in just about every sentence of the original poster. This will certainly be the type of woman who will attract men who want that and most likely they will be similar types to herself, so she shouldn’t be surprised at who she attracts. The point is, you have to know yourself. Then you can adjust your dating preferences and goals for relationships based on that knowledge. Too bad we learn so late in life…

    1. 49.1

      I wish that one of my friends could read your postings (to ocdgirl2000).  

      I have a male friend in his late 30s that makes statements like “beautiful women graduate from high school everyday and there will always be someone finer than your wife”.   Nevertheless, he actually justifies men leaving their wives if she does not immediately lose weight after pregnancy.   He said that, if he is married, his wife “better lose weight quickly”.   He always goes after younger women and make them think that he wants a commitment when he doesn’t and he is very superficial and judges women on their weight, hairstyle, and will dump a woman or cheat on a woman as soon as he finds someone prettier or she doesn’t wear a hairstyle that he likes.   He is getting older and older but still seeking recent high school graduates for sex.

      I wish that he could hear it from the other side, of what that life really brings after years of marriage.  

  10. 50

    I’m so sad for Ashley. Who would have ever thought?

  11. 51

    Yay Evan! I like your stance. Being the pretty girl isn’t the easiest job in the world though some may like to think so! AND hearing a man oppenly acknowledge that fact is just amazing. You should forward a copy of this to the entire male population (and female too) so that perhaps finally we too can be understood.

  12. 52

    To Hunter,
    I am not sure what you mean by “in my prime” but I look for someone who has something to say and good skill in the art of conversation. People would spontaneously tell me what a beauty she was, even now when we are in our 50s. The othe ingredient is the mutual love and respect that binds us together.

    Conversation? There was a time we went off to europe and spent a month touring in a small car with no one but each other to talk to in countries where we didn’t speak the language. While we spent ample time experiencing the romantic possibilities of places like a tiny hotel in a 13th century french castle, ultimately, it was the conversation that carried us through the day.

    Of course, great conversation also implies shared core values. I don’t long enjoy talking to a person who is dishonest or not trustworthy. A willingness to openly talk about themselves. and ultimately a willings to be emotionally engaged. make long term good conversation possible.

    Attractiveness is just that. After you have gotten each other’s attention, what you do afterward determines whether you progress beyond dating.


  13. 53

    Post #25. Though I am not a pretty woman ( and couldn’t be one even with drugs, a chain saw, and a bucket of paint ) I found your advice fascinating.

    People in general, are not likely to give feedback, particularly in dating related situations. No surprise there, it is usually a thankless job, even when solicited. You can expect hurt feelings, arguments and/or an awkward situation.

    I think your advice may work because the dynamics change. You basically have a good looking woman doing something that most men welcome: paying more attention to them by asking them for their opinion.

    Not useful to most of us, but for those helping good looking women friends with dating problems your advice is valuable enough to file away.

  14. 54

    Hunter, Brian; About post #52. I concur.

    I am in my “prime”. I look decent, am fairly well rounded on the inside and I have a decent financial situation. I would still like to have sex with many more women, whether or not they are relationship material.

    It might be a sign of being a little bit on the lonely side these days, but I see a good conversation with someone I connect with as valuable as a wild night of mind blowing sex after a pick up.

    There is just something about finding a kindred spirit that is life affirming, complex and interesting.

    Then there is always mind blowing sex afterwards 🙂

  15. 55

    To Steve,

    Stay on the internet, I have been told there is pick up artist information, if you keep looking.

  16. 56

    I always wondered why the really pretty women don’t participate in beauty pagents, now I know.

  17. 57

    Evan – I think you advise is “right on.”

    To those of you that think being pretty is so easy. The majority of my life I was shy, quiet, not attractive and blended into the wall. I finally found my confidence and I am now comfortable with my looks. I don’t think I am a 10 but do get a lot of comments about being gorgeous, sexy and attractive. With that said, I can totally relate to Ashley’s problem. I think all women with self esteem problems think the pretty girl has it easy but after changing into that girl, I see quite the opposite. I used to envy a girlfriend for her good looks but never understood why she never wore makeup and never dressed to show off her figure. Now I totally understand why. When you get tired of the same patterns of men (even women) not taking you seriously and just seeing your appearance, you just want to find someone that likes your inside and the outside is a perk. I spent my late 20s and most of my 30s married. Coming back on to the dating scene with my new found confidence about four years ago, I find it really hard to find the good guys (guys that meet my standards and want the same things in life as I do). Here’s what I’ve learned.

    Ashely, you are going to have to weed out those that take you for only your looks. If you are on-line dating, try to get to know someone before you meet and make sure you just don’t accept a date because he asks you. If you are okay with not accepting every date (it’s not your social life) make sure there is something in it for you and what you want. If you don’t accept every date, you have to be willing to be alone. I find that I waste my time and his if I just go out because I get asked. Also, most guys under 40 don’t want a serious (get married) relationship. Actually I am finding that even those that have been married don’t want to marry again.

    And a few comments:
    Kristina post 29 wrote: “If these woman are single it’s for one of two reasons- either they want to be single or they are doing something that is causing them to be single.” – Get off your high horse! It really isn’t that simple, everyone is unique and has a unique situations.

    Nikita post 9 wrote: “So when you see that beautiful woman walking down the street, don’t just envy her, she may be more insecure than you expect and that aloof exterior only a front to ward off unwanted advances. Spare a thought, give her a smile and start a sincere conversation with her. You never know that she might say yes.” – I second these statements and it goes for women of any age or anyone in fact!! We are all human!

  18. 58

    To heather,

    How true!….Some women don’t dress to enhance their figure. I remember dating a woman, who, at first sight, seemed to be, in the “plain, average” looks category. Until, we took our clothes off did I see her sexy figure. hhhhmmmhh…EEGGAAADDS!..

  19. 59
    Dr. Tartt

    Well said Evan! I wonder if we have a case of self-fulfilling prophecy going on? I wonder how long she really expects to maintain a man’s attention. You attract what you expect.

    Dr. Tartt

  20. 60

    Hey Ashley, HAVE FUN and stop worrying so much about “settling down.” That’s enough to make any guy cut and run, and they do pick these things up. Whatever is meant to happen will happen. Making that leap from dating to commitment has a lot to do with “right place, right time,” and you can’t control that. So what if these particular guys didn’t work out? Go out and do something you enjoy, and get to know the guys who are taking you out — maybe they feel like you’re not giving them a chance. You don’t have to give up your morals or standards, or anything like that, but I think you owe it to yourself to have a good time. You don’t want to look back in 5-15 years and slap yourself.

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