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. 81

    this is difficult pretty girls are always wanted by bad guy so you must have ability to differentiate between good boy and bad boy

  2. 83

    Good Evening Everyone,
    Thank you all for your lovely and even controversial posts.   The more we communicate, the more we learn, and the more compassion we can have.
    I am pretty.   I am.   Even I know it.   And at various points I have Hated going to the grocery because someone was going to stare or follow me down an aisle.   It is the pressure that I find so disconcerting – I have felt that I just wanted to hide rather than to be objectified.
    Finding myself single in the middle of nowhere was very lonely.   I relocated and joined a few of the online dating sites and I attract men from 27 to 60 something and find at least 3 – 4 emails a day from new suitors.   Yes, there are plenty of fish – and they all want to take a swim in my tank!   But who will be there to clean it and feed me when they’re done gawking at how exotic I am?   I tell my girlfriends, “Can’t talk now – gotta go feed the fish!”
    And yes, I joke.   But I want to be Seen for who I am – like other posters have said – not what I am.   And I am new at this and do not have a good sense yet of who wants me and who wants the pretty.   It feels bad to be standing right in front of someone and to feel invisible.   Really, really bad.   In this way, I am insecure.   I don’t know how to discern one from the next yet.   Does anyone have a good litmus test or a polite question worked out to get the information you need?
    Karl R – Thank you for being so considerate.   I will say that while some men don’t find me as attractive as others (just as a matter of preference) it is still very nice to receive a compliment to know that you think we’re pretty.   However, if you were to compliment me on the person that I am and my unique qualities you would be my hero!
    For Janice and OCDGirl – we should be friends!   We could wear awful, baggy clothes, no make-up, practice up on bad hair and go to dance clubs!   We could laugh, dance for fun and not give a flip!
    Best to all ~

  3. 84
    Karl R

    Flora said: (#84)
    “And I am new at this and do not have a good sense yet of who wants me and who wants the pretty.”
    “Does anyone have a good litmus test or a polite question worked out to get the information you need?”

    This will come across as a completely geeky suggestion, but have you considered meeting people through an online game where nobody knows what anybody looks like? (World of Warcraft, Second Life, Everquest, City of Heroes, Eve Online, etc.)

    I know that a few celebrities play these games in order to socialize with people in a setting where they won’t be treated as special. They’ll just be treated as another one one of the guys (or girls).

    You will get some people who will still treat you like you’re pretty if your electronic representation of yourself is female and attractive, but most of the mature individuals will treat you according to how you interact with them and the rest of the world. (Not just socially. You’ll earn respect for playing the game competently, for example.)

    While a few people have met their significant others through online games, I wouldn’t expect that. What you really want to learn from this is how you like to be treated by others  … when your looks aren’t part of the decision making process.

    That suggestion might not appeal to you. That’s fine. I did want to give one example of how you could get to know a group of people very well without having them know what you looked like.

  4. 85

    Unless you do something basically blind like Karl’s suggestion, there’s no way to know whether someone likes you for who you are, rather than what you are, without letting them actually  get to know who you are.

  5. 86

    Most men don’t really bother with the pretty girls because there is an assumption that they already belong to that small group of players/pick-up-artists who bag beauty after beauty every single weekend.
    Sadly, those same players also dip into the pool of ‘average’ women which leaves most men marrying a girl who has been sleeping with players her whole life while he sat by the sidelines.
    Women really should try to date their equals, rather than all of them reaching for the top of the crop.

  6. 87


    Thank you thank you thank you!!!! I have never had anyone verbalize exactly what I feel until just now!   Objectified is exactly the feeling and sifting through the sincere unthreatened men vs the slime balls is a full time job if you let it.   Just like anything else genetically, I did not choose how I look, it just is.   Also, the worst feeling is ending a relationship, as I just did, not knowing if the guy is really just threatened.   I am a loyal, good, funny and good person, who happens to be attractive as well.   Why do people think those traits have to be contradictory?   I agree with the comment that this is the best post yet!

  7. 88

    Another thing on that!   I cannot stand people who think that you should just ‘walk it off,’ when rejected or being the center of attention just for your looks, as if  that is the price you pay.   I used to say that celebraties should get used to the papparazzi because they are in the public eye but they still have rights to their lives and to privacy.  
    I have had women try to sabotage my means of earning a living because they felt intimidated by my presense.   When I confront them or try to defend myself, I get the “poor me” sarcasm and it beyond hurts.   Thanks so much Evan for putting to words exactly what I’ve experienced my whole life.

  8. 89
    Karl R

    Lisa said: (#89)
    “I cannot stand people who think that you should just ‘walk it off,’ when rejected”

    As an active dater, what other option do I have when I’m rejected?

    I could continue  to pursue the person who isn’t interested in me. (I’m sure you hate it when the men you’re not interested in do that.)

    I could swear off dating in order to avoid further rejection, which would be counterproductive to my long-term relationship goals.

    I could wallow in depression for days (or weeks), which probably wouldn’t be healthy for me.

    I could go to my friends for sympathy, but they’d probably get tired about hearing me complain about being rejected. As a guy who was an active dater, I was getting rejected a few times per month.

    The only sane and sensible response I can think of is for me to shrug off the rejection and find someone else that I’m interested in.

    I’m assuming you can’t stand that advice because you believe it’s bad advice. Can you  suggest a better course of action that people should pursue when they’re rejected?

    1. 89.1
      Evan Marc Katz

      @Karl – Dude, I should pay you to be my surrogate. Thanks for reinforcing the logical point of view when I’m not around.

  9. 90

    @ Karl #90 – I’ve got a question. While we’re on the subject, can you (or any of the other men on here, as a matter of fact) tell me how/in which way/how soon do you prefer to be rejected? I want to let people down with minimal pain, so we could be friends and/or business connections afterwards. So far, I’ve failed miserably. Over three months with one person, I gradually went from “eh, I didn’t really like it when he said that, but that’s a minor issue, the guy and I have a lot in common, I should give him another chance” – to “this man is so wrong for me and I so want this to end – but he’s got all those things planned and it would really hurt him if I ended it now – let’s give it another few weeks and then maybe it’ll end on its own”.
    So it got to the point where he asks me “So, are we exclusive?” and I look at him and realize there’s no way in hell I want to be this dude’s girlfriend.
    So I start hemming and hawing. Which in turn made him really mad, because apparently he hadn’t been expecting any answer other than “yes”. Chewed me out for fifteen minutes, went home and deleted me from his Facebook immediately 🙂 And I’d really hoped we could have some business connection going on. We share the same hobby and could be of value to each other in that regard.
    The only thing I can think of is that I blew this one. Apparently, somehow by being polite and nice, I led him to believe I was madly in love with him, when in fact I was frantically looking for an exit. What can I do differently next time?
    As for rejection, IMO it is a blessing in disguise. It means you wouldn’t have been happy with the person, and, rather than wasting your time, they let you go, thus allowing you to pursue better opportunities – be it your work, hobbies, friends, seeing other people, or all of the above. On the subject of rejection, I really liked the “Just Got Dumped” post on this blog. Of course you shouldn’t “walk off” after a rejection. You should skip happily off, thanking the other person that it happened now and not twenty years into your marriage 😉 I understand it’s hard to do when emotions get in the way, but logically, rejection is absolutely a good thing.

  10. 91

    *rather than waste your time*. I manage to sneak at least one grammar error in each one of my comments. Oops.

  11. 92
    Karl R

    Goldie asked: (#92)
    “can you (or any of the other men on here, as a matter of fact) tell me how/in which way/how soon do you prefer to be rejected?”

    How soon:
    As soon as you know that you don’t want the relationship, you should let  the other person  know. The earlier the relationship ends, the less painful it will be. The longer you wait, the more invested the other person becomes in the relationship.

    In which way:
    That depends upon where things are in the relationship. If you’ve only been out once (or not at all), a polite “No thank you,” when he asks you out is sufficient.

    If you’ve been dating longer, a face-to-face breakup may be the most appropriate way. It’s best to be someplace reasonably private while  you’re breaking up, and someplace  where you can leave after you’re done breaking up. (The other person’s home is one option if you’re sufficiently serious.)

    Be clear and decisive. For example, don’t say, “We should stop seeing each other for now,” unless you think you may start  dating him again later.  Instead say, “We should stop seeing each other.”

    Make it about you, not the other person. Some examples:
    “I want lots of kids, and you don’t want any.”
    “We’re at different stages in life, and I’m not comfortable with that difference.”
    “I just don’t feel that there’s the kind of chemistry between us that I’m looking for.”

    Be brief. The person doesn’t need to know every reason that you’re breaking up. One reason is sufficient.

    The other person may still get angry/upset. You’re not there for a fight. If they get angry, that’s your cue to leave.

    If you have any reason to believe that the other person might respond to the breakup with violence, take precautions to protect yourself. You can breakup in a semi-public place (with lots of bystanders who can’t overhear your conversation) or you can breakup by phone.

    Goldie said: (#92)
    “I understand it’s hard to do when emotions get in the way, but logically, rejection is absolutely a good thing.”

    It’s a lot easier if you don’t think of it as “rejection.” I think of it as, “She’s not interested in me,” or “I’m not the type of guy she’s looking for.”

    There are a lot of wonderful women that I’m not interested in for one reason or another. Therefore, it’s not a big deal if some wonderful woman isn’t interested in me for one reason or another.

  12. 93

    Thanks, Karl!
    As soon as you know that you don’t want the relationship, you should let  the other person  know.

    Ah, but my problem is that it takes me forever to find out. I’m always like, “This must be all in my head, I must be overreacting, it’s not that bad”… How do you think I stayed married for 18 years? 😉 Guess this takes practice. I’ve definitely been analyzing what went wrong in my particular case, and how I could’ve caught it earlier.

    It’s a lot easier if you don’t think of it as “rejection.” I think of it as, “She’s not interested in me,” or “I’m not the type of guy she’s looking for.”
    Absolutely agree. Or, as I think of it, “if we get together, none of us are going to have a good time”. If the guy thinks we’re not a good fit, then we’re not a good fit, so, moving on is in my own best interests 🙂

  13. 94

    There seems to be a lack of chemistry with the men she is attracting.   She says she attracts many men, but I don’t remember if she described them well. Is there a particular *type* of guy she’s attracting? If so, she can avoid that type in the future (the no-chemistry type), and date someone the opposite of that. It worked for me. I’m   pretty average looking. I always tried to date quiet, bookwormy guys, since I’m a quiet bookwormy girl, but no relationship ever sparked. So, I changed my tactic, and went out with a louder, physically more assertive guy, whose personality is almost the polar opposite of mine. When he told me his uncle manages a strip club and he has dated lots of strippers, my first impulse was to quit seeing him but I fought the impulse. Turns out, the chemistry of opposites is HOT HOT HOT. We did break up for a while and we both dated other people for a few months, but we’re back together now. He told me he just “couldn’t stop thinking about me”. 🙂 He   talks marriage and longterm stuff a LOT. Fingers crossed this is the one.   It’s as close as I’ve ever gotten to finding the “One”.

  14. 95

    evan, thank you so much for writing this… ive never seen anyone describe my experiences so very well.   not sure if this post is very old but i am going to comment anyway.
    im a 28 yr old attractive woman, which i would never normally say for myself except that i get hit on constantly and chased like crazy.   i am also incredibly shy/reserved, which comes off as coldhearted and aloof.   im not really insecure, just feel harassed and bothered by all the attention.
    if i was a happy smiley girl i would get talked to nonstop, so i have developed this serious face that i use when out in public so that im nearly unapproachable.
    i still get dates and boyfriends but have exactly ashleys problem.   in fact i have a phd in science, which makes it HORRIBLE in trying to determine if someone is actually ‘listening to you’ or ‘looking at you.’   i feel i am never taken seriously.   i am very difficult to talk to because i assume any strange man who is talking to me just wants to hit on me.
    i am actually pretty lonely sometimes.   it is hard to have female friends because females are naturally competitive and i have no interest in that.   i do better with guy friends (and ignore the subtext of them being attracted to me).
    at this point i subconsciously choose relationships with men who do NOT compliment me, hold out on praise, and tease.   after a while in these types of relationships i feel undervalued and unsupported, craving someone who compliments me.   its a bad cycle.
    i realize this sounds so bratty but for a shy person, being pretty is a bit of a curse!

  15. 96
    No Crap

    I know EXACTLY where Ashley is coming from.   And I agree with her.   I would absolutely NOT let my guard down unless/until a man showed that he was worthy of my trust.   If a man is so intent on having sex that he can’t wait until I’m ready, whether it’s date 1 or date 21, then I don’t want him.
    Basically, the way I read Evan’s advice is, if a man has looks and money, he gets what he wants.   If a woman has looks (and maybe money) she has to put herself on the line to be (potentially) used and abused because, well, men always get what they want, don’t they?

    1. 96.1

      #99- No Crap – Nowhere does Evan say that “men always get what they want” (I’m sure there are plenty of men in the comments who would disagree with that!) or that ANY woman – regardless of looks or finances – has to put up with being “used and abused”… His new book, Why He Disappeared, is all about how NOT to feel used and to empower yourself to get the love life you deserve…

      It sounds like you’ve been hurt before, NC, but that doesn’t mean ALL men are sexual deviants who don’t care about women’s feelings and only want one thing… And it doesn’t mean that some women don’t enjoy sex outside of a committed relationship. If you never let your guard down and treat a guy like he’s untrustworthy and constantly has something to prove before he gets the prize (sex,) then why would he stay?

  16. 97
    Karl R

    Misha said: (#97)
    “at this point i subconsciously choose relationships with men who do NOT compliment me, hold out on praise, and tease.”

    You just validated the tactics used by Pick-Up Artists to score with attractive women.

    Misha said: (#97)
    “after a while in these types of relationships i feel undervalued and unsupported, craving someone who compliments me.”

    At least it sounds like you dump them quickly, even if you don’t consciously recognize them for what they are.

    Misha said: (#97)
    “i have a phd in science, which makes it HORRIBLE in trying to determine if someone is actually ‘listening to you’ or ‘looking at you.'”

    That’s not an either/or situation. Men aren’t that bad at multitasking. They are looking at you. They may also be listening to you.

  17. 98

    If you genuinely don’t want men to hit on you, such as in professional settings, don’t dress or act in a way that would be seen as a come-on. Dress conservatively, put your hair up, don’t cake on the makeup, don’t tilt your head and smile. (But ah, therein lies the rub, no? How many of us, deep inside, really don’t want to be attractive?)
    Misha #97, your situation is not all that uncommon. I’m marginally pretty at best (a 6) and married, yet get hit on constantly by virtue of being a woman in a male-dominated scientific field. What you’re doing is exactly right: don’t smile too much, be aloof. Don’t worry that aloofness turns people off. When it comes time for you to be promoted, they don’t base it on how much they like you or whether you let them come on to you; they base it on the quality of your work. Keep focused.
    Accept that if you’re beautiful or even marginally attractive, you will get hit on. Don’t take it personally and don’t get angry or resentful about it. That just hurts you, and does no one any good. Understand that it happens to many, many people, even plain Janes. You’re in good company.
    If you have lots of men after you, how can you tell whether it’s worth giving them a chance?   Look for evidence of kindness in the men who pursue you. One way is to observe how they treat other people, not just you (the beauty queen).   I’ve seen it over and over again: if a guy is nice to you but mean, dismissive, or rude to others, he is NOT worth getting into a relationship with, and will eventually treat you poorly too. So, look beyond yourself.   At the very worst, you will end up dating lots of nice guys who may or may not be compatible with you. Not such a bad fate!

  18. 99

    While I won’t rate myself with a number (I find that SO offensive frankly), I have often been described by others as “pretty.” For me, the problem isn’t the men at all. It’s the other women. Many don’t want me anywhere near their boyfriend/husband and make sure I’m not included in their social events. Note to all women: I DON’T want your husband/boyfriend. PROMISE. Even women I considered “good” friends have said they don’t want to go “out” with me because it makes them feel ignored/unattractive when I get attention and they don’t.

    I often feel very  shunned by  women in general . . . hated even. Maybe this girl should look closely at her “supposed” friends. They  are likely  bashing her to any man who will listen (particularly the men they are interested in). I find it much easier to be friends with men – but then yes – the next problem is that they have very little interest in being “friends” per se. And the men you do date tend to have a problem with the male friends . . . So you end up feeling isolated, alone and without any true friends.

    To the poster –  Take a  long, hard  look at the  men who are willing to be a “friend” versus a “date.” That’s when you’ll hit the mother lode. I’d also take a long hard look at your female “friends” or social group. That could be where  another major problem lies.

  19. 100

    #102 Vicki

    I often feel very  shunned by  women in general . . . hated even.

    I’m always suspect when women claim that other women hate them.   And  the woman who is  hated  typically says  all the other women think they are taking away their men.

    If it’s one or two other women, those could be those women’s issues.   If it’s ALL  women the person is coming into contact with, then one has to look to themselves to determine what is going on.   Whether they are attracting insecure women to their lives, or they have some sort of insecurity going on where they are seeing things in a certain way, oversensitivity,  behavior, etc.

    Women successfully survive by having a strong network of women friends, it’s in our DNA.   That’s if the woman has a man in her life or not, it’s very important.   We instinctively seek other women out and it defeminizes us when we are excluded.

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