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. 61

    I feel that many attractive women act or believe that with their good looks comes a sense of entitlement. As in “Since I’m attractive, I only want to date hot, tall guys who drive nice cars” And that is fine; because they can get those kinds of men to date. But since really hot men are more scarce than really hot women, the men who these women attract tend to have lots of choices and are likely to be players. Attractive women, need to examine the types of guys they are dating — My feeling is that after a few mis-steps, if the same bad thing keeps happening, then you have to wonder if it’s the fault of the chooser (i.e. the hot girl), not the choosee (i.e. the men she dates).

  2. 62

    to Mike,

    I have heard therapist say, “a single womans downfall, when she selects men with her eyes.”

  3. 63

    Mike’s #61…

    “I feel that many attractive women act or believe that with their good looks comes a sense of entitlement. ”

    So do many non-attractive ones too.

    Ignore them. You do yourself a favor.

  4. 64

    And people assume the pretty girls have it easy… well in some ways they do 😉

  5. 65

    I had a debate the other day with my friends (a guy and his girlfriend). I stated that “in our looks-based society, there is no reason why an an attractive woman can’t find a boyfriend. If she can’t, then she is not trying hard enough.” By “not trying hard enough,” I meant that she’s either not putting herself out there, or that she is not spending enough effort in filtering out the wrong types of guys. My guy friend agreed with me, but his attractive girlfriend completely disagreed. Your thoughts?

  6. 66

    To Mike,

    Most women could marry this instant, if they dropped all their requirements……..Attractive women can’t go to the grocery store without being approached by a man, almost always the wrong one,(so they say)……. these women don’t need to put themselves out there…..they are constantly getting hit on.

    You bring up a good point, attractive women do get tired of dealing with all those personalities(get tired of filtering out guys)…but this usually doesn’t happen ’till they turn 40,(and lose their hormones) or if they get hurt/abused.

  7. 67

    to Adam,

    #64, Your post brought to mind an old USO show with Bob Hope and Raquel Welch. Bob said that when he invited Raquel to come on the show, she asked him, “what do I have to do?” Bob replied, “You don’t have to do anything, just stand there, most men know what to do.”

  8. 68

    So the beautiful have it just as tough as the not-so-beautiful. I’m sure that the not-so-beautiful would be willing to trade one set of problems in for the other, if only for a little while.

  9. 69

    to post #68

    LOL!…but only if life were that simple and easy going…a womans mind does not operate like a mans mind……

  10. 70

    Being strikingly attractive can be a problem on its own. People comment on your looks without having to bother with who you are at heart. A beautiful woman is something everyone wants to have even though they are sure that many have got it.

  11. 71

    “Most women could marry this instant, if they dropped all their requirements..’

    Hunter, really — what an attractive proposal for the woman.

    “I, Attractive Woman, take thee, Unattractive, Unproductive Blob with No Intelligence, Feeling for Family, or Charm …”


    I know that’s what a lot of you seem to want; it’s one of the reasons why Apatow’s and Braff’s movies are so popular, it’s all wish fulfillment.

    But really …


    Do any of you men see how inequitable that is? You want a woman to have everything to offer you, but you want to offer her nothing? Do you really think that’s the way things are supposed to be? Do you care at all??

  12. 72

    Post #71

    Ha!,…..how funny!….”unproductive blob”….I didn’t mean just grab a man from the “pile.”………… Single, very productive men, do exist, although, maybe, in a smaller pool, and mostly, clueless.

  13. 73
    Karl R

    “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 have a question for Heather and the other attractive women who have voiced opinions on this subject:

    What would you think if a man was clearly interested in you, but he did not compliment your appearance?

    When I begin dating a woman, I tend to compliment her on other traits (intelligence, humor, skill as a dancer, ability to live in the present, etc.), but I tend not to compliment her on her appearance until I’ve known her for a while. The more attractive she is, the longer it will be before I compliment her appearance. (This isn’t something I consciously plan, but it’s a habit of mine that I’ve observed.)

    So if you’re interested in a man, and he’s clearly interested in you, would it bother you if he offers fewer compliments on your looks than the average man? Or would you be happier knowing that he clearly appreciates qualities other than just your looks?

    1. 73.1

      Actually, I can speak for many women when I say that we enjoy getting any compliments, so long as they’re sincere. A man telling a woman, “Hey baby, great ass!” will not be as appreciated as one who says, “Wow, you look amazing” and gives you the onceover. I, for one, love it when a man I’m out with compliments my looks. It takes a lot of effort to look good and he damn well better take notice! Plus, funnily enough I am much more likely to be physically attracted to someone who makes me feel beautiful by complimenting me. I just went on four dates with a guy last month who told me repeatedly how much he loved my personality. But he never once said anything about my looks. Not even the aformentioned “how nice you look” kind of thing. Combined with the fact that it took three dates before the guy would kiss me on the lips, and another before he would get touchy-feely, and you have a recipe for disaster because, as you can guess, I was no longer interested at that point. He took too long and didn’t do enough to stoke the tiny flame I had in the beginning into a bonfire. Women love it when guys flirt and give us compliments – you neglect to do so at your peril.  

      1. 73.1.1

        Sorry, J, but if you dropped a guy just because of that, then that tells a lot about you.

        1. hunter

          Joe, I agree….


        2. Emily, the original

          Joe and Hunter,

          Combined with the fact that it took three dates before the guy would kiss me on the lips, and another before he would get touchy-feely,  

          Sorry, J, but if you dropped a guy just because of that, then that tells a lot about you.

          I don’t agree. He never complimented her on her physical appearance and it took him 3 dates to kiss her. Either he’s not that into her or he’s not particularly adept at making a move. Some women find that endearing. Others don’t.



      2. 73.1.2

        Uhhh, she dropped him after just four dates, just because he did’t mention her appearance, and she didn’t get a kissey kissey.

        He dodged a bullet.

      3. 73.1.3

        You know how sometimes we women say we are damned if we do and damned if we don’t when it comes to dating.   I sometimes feel the same thing happens to guys.   How many women on this blog have lamented the fact that all men care about is looks — they don’t care about their intelligence or accomplishments.   So, this guy compliments you in the area that many women want to be complimented in and he gets dinged for it.   I am not saying you are wrong, I’m just saying….Also, not many  guys go out with a woman four times if they don’t find her attractive.   Also, I know when men find me attractive even if they don’t say it.   I see it in the way they look at me.   There is a hunger and a lust and I know when it’s there and I know when it isn’t.    Finally, this guy may have been holding off on getting touchy feely because what’s the other thing we women complain about?   All men want is sex.   So, he takes it slow and gets dumped for it.

        So, there you go.   In the world of dating both women AND men are damned if the do and damned if they don’t!

    2. 73.2

      As a superannuated hottie, I definitely preferred when men would let me know that they found me funny, kind and intelligent and then showed me – through great makeout sessions 🙂 – that they found me attractive.  

  14. 74

    Hunter, if you’ll look carefully at the top of my post you’ll note that I quoted you back to yourself EXACTLY.

    “I didn’t mean just grab a man from the pile.
    can easily be construed as a reasonable conclusion drawn from the assertion
    Most women could marry this instant, if they dropped all their requirements.”

    The thing about communication is that, if you want to be perceived as effective at it, you have to be willing to take some responsibility for
    – what you said (the literal words, the tone of voice, and the connotations) AS WELL AS
    – what the other person heard.

    And if you don’t give a hang about what the other person hears you say (because I can hear you now – “I can’t be responsible if some woman reads things into what I said!”) — then you’ll understand if she thinks you don’t give a hang about communicating with her effectively.

    If you didn’t mean “drop ALL her requirements”, then don’t say that.

    And if that IS what you meant, then I’ll ask you again — do you honestly think it’s an equitable relationship if you want a woman to have everything to offer you (and be willing to do so) but you want to offer her nothing??

    Moving on:
    Single, very productive men, do exist, although, maybe, in a smaller pool, and mostly, clueless.”

    How is this relevant to women “dropping all their requirements”? What does cluelessness have to do with anything?

  15. 75

    to M, on post #74

    on, “drop all her requirements.” hhhmmmhh, relationships, won’t operate on precision. I said, “all” but in a general sense. Say, are you a military/correctional officer?…….or maybe in the legal field?……..how funny!…..

  16. 76

    I think it’s true that everyone has their fair share of hardships. I just don’t think that men only go for looks, which is not true of all guys but if they want a real partner, looks are only part of it. Instead, look for people you connect with in other ways. Show men how smart, talented and funny you are. Those are the types of things that men who are looking for a relationship, will ultimately factor in. There’s more advice about this sort of dilema on vdateonline.com. I’m always looking on their forum for advice and tips. There’s great advice about showing the inner you on there as well.

  17. 77
    Dating Reviews

    A rather blunt post, but there is some truth to the advice. I agree that women should not become objects to men!

  18. 78

    I am engaged now, but before that, there was a long list of guys who did exactly what you said (assumed I was dumb or intimidating, etc.). I’ve never heard it so perfectly put.

    Sometimes I say to my fiance, “I don’t know why you love me.” I do know why he loves me, it’s just that I can’t believe he really does. I don’t by any means think I’m the most gorgeous woman on the planet, but my fiance for some reason does. The difference is that he acts upon it in a much different way than his predecessors. Pretty girls often need to be treated in a more gentle way. Telling us we’re hot and you want to sleep with us won’t cut it.

  19. 79

    Found this site interesting.  I will be entering the on-line dating world soon.:-)  Never thought I would have to, but here I go.  I only had three boyfriends in my life and those relationships were very long term and serious.  Each resulted with a job relocation by their company.
    I have friends and relatives asking me why I have to go on-line to try to find another boy friend (my fiance was transferred out of state) as men stare at me when we are out.  That is the problem.  Men just stare. 
    Women stare.  It can be lonely in a way because people just stare.
    I really enjoyed this site and this topic because I am learning about what I will have to post on the dating web site.  I mean, I am understanding about what others may think when they see my image up.  I know now that I will need to word a profile that highlights what I do for a living (work with children), how I contribute to society (work with volunteer organizations for children and the elderly), about my passions that are about helping others — basically, I will not let my photo have more weight than my substance.:-)  Just one plain head-shot image will be used. 
    Anyway, thank you all for your words concerning this issue. 

  20. 80
    Christie Hartman

    This is a great post that brings up an important issue, an issue I address in my books and with my clients. Beautiful women have it tougher than people think – they attract more men but they also attract a lot of douchebags and men looking for conquests and trophies. I encourage very attractive women to be on the lookout for this and not rely on their looks because, ultimately, men want to a woman they love and connect with, not a trophy.

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