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. 21

    Lance is right on – men want to be with a beautiful woman, and will do anything to be with her. To use EMK’s terminology, men want a trophy. So if the guys are leaving after one date, something’s wrong. She must be de-attracting them. Maybe it’s the sex they want and she won’t give. But who knows?

    Some beautiful women know they are trophies to men, and use that to their personal advantage. They play men for spas, getaways, jewelry, etc. A lot of men who figure this out will simply leave them for someone else. Maybe this reader expects too much material attention, and the guys see right through that?

    Wealthy men who are seeking a genuine connection face the same problem as a beautiful woman seeking that. It sucks when women see you only for the size of your wallet.

    1. 21.1

      These beautiful women you are referring to are probably in the prostitute category, this is a big misconception with men that beautiful women are high maintenance gold diggers. Instead of looking at the bigger picture and the fact that there are good/bad people everywhere.

  2. 22

    Selena May 22nd 2008 at 03:42 am 16
    Actually, not wanting to have sex on the first couple dates is a rather common position. Which makes me wonder if Ashley is either picking I’m only here for sex kind of guys, or if there is something in her demeanor on a date that is making them leery of dating her further. We need more info than just her statement she is a very pretty girl.

    Ditto & Amen.

    I am a nice guy, decent looking, not in a bad spot in my life, & I have Sicilian blood coursing through my veins. I don’t expect nor I do I even want sex on the first few dates. Its nice to take a little bit of time to get to know the person first. You know, last name, paper versus plastic, Kirk or Picard, etc. 🙂

  3. 23


    Post #19. Yes, nice girls recycle!

    Seriously, I’ve had your experience and I know where you are coming from. Looks will get me there, but they are not enough to keep me around.

  4. 24

    “. . . men want to be with a beautiful woman, and will do anything to be with her. To use EMK’s terminology, men want a trophy.”

    Wanting a trophy might be superficial, but the great feeling you have from being with one is absolutely genuine. I’ve only dated a 10 once in my life, but it boosted my self-esteem more than being hired by my jobs and more than getting into an excellent college. Dating a 10 inspired me to improve myself in various ways too, from exercising more to improving my mind to even trying to get along with my parents better.

    Just because I got a lot of joy just from being seen with this girl doesn’t mean I didn’t sincerely like and respect her though (she was as smart as she was good looking). And just because I worshipped her for her looks doesn’t mean that I would put up with anything from her either, in fact, the reason we broke up was that she didn’t do as much to try to make me happy as I did to make her happy.

    My point is that a trophy brings genuine, if superficially induced, happiness.

    We are who we are and looks matter.

  5. 25


    Based on your post, I get the impression that you may be a little reserved. If that’s the case, what you think be open and inviting may not be interpreted that way by the men you are dating. Although you may feel that laughing and smiling and having a good time is a clear signal to a guy that you are open to seeing him again, it may not be so obvious to him. Seems crazy, I know, but it’s true. So, if you really are having a good time with a man and you want to go out with him again, you may want to send louder, clearer signals. I am going to suggest a few simple things that you might try.

    First, make certain that you really pay attention and really listen to what he is saying and ask follow up questions that indicate you are genuinely interested in him. Get him to talk about the things he loves.. his passions…not just his job. Don’t make him feel like you are interviewing him — you aren’t. You are just trying to get to know him. Make certain that you are looking him in the eye when you talk — don’t let you eyes wander all around. Make him feel like the center of your attention.

    This next can be a hard habit to break if you do it — don’t cross your arms when you are with a guy that you like. It makes him feel that you are closed off and not interested. Lean in to listen when he talks to you. It might be the subtle things that put distance between you two that may make him feel you aren’t interested.

    Make up reasons to touch him — in a fun, playful and clean manner… ask him to thumb wrestle or tell him you want to read his palm. Voluntarily touching a man is definitely a signal that you are interested!

    Offer to pay your share. Be gracious if he wants to pay for you.

    Finally, at the end of the date, just be bold and tell him you had a good time and would enjoy seeing him again. Doing any or all of the those things will be no guarantee that the guy will want to see you again if he’s “not into you.” However, you can at least be certain that he knows that you were interested in him!

    Also, as another poster suggested, it can be really illuminating to ask a guy what he thought about you on a date. I’ve done this myself and a number of the guys told me they just didn’t think I was interested in them. Like you — I laughed and smiled and had a good time so I was actually shocked that they felt I wasn’t interested. That’s how I know from personal experience that laughing and smiling and having a good time are not enough of a signal for some men. Given that you are so attractive, a guy may need even more reassurance that you like him. So, just help him out a little more!

    Good luck!

    1. 25.1

      wow..sounds like as a woman you must cater to the man! what women want a guy like this?? guys need constant reassurance they are liked, need a woman to pay their way, and need to be doting and focus on his needs and wants–lol? no this ISNT good advice…this is teaching males that they are the center of the universe and women are to cater to THEM which is the reason most males have turned into the narcissistic jerks they are…

      1. 25.1.1

        jenn, as opposed to women thinking they are the center of the universe?
        It works both ways.

        1. deon89

          thank you. lol


  6. 26
    Evan Marc Katz

    Hey Eda,

    If you keep giving great advice like this, no one’s gonna need a dating coach! Glad to see you’re implementing these solutions in your life.

    Hope all’s well.


  7. 27

    Oh, Evan,

    We will always need you 🙂

    By the way, your video clip is awesome! I hope that was just the first of many more to come.

  8. 28

    I’m thrilled to hear about a hot young girl having a problem dating. Yeah, that might make me sound bad, but I’m happy to hear it because it makes me feel better. Honestly, 7-9 girls have the same problems as “10s” with wondering if he’s into us or just using us for sex…albeit with smaller numbers of guys chasing us. Guys are guys…so Ashley is going to have to keep relying on her judgements just as the rest of us women do.

    As to what Eda said, I agree. Ashley does need to flirt appropriately. Touching him (shoulder, arm, knee) a few times on the date is a great, easy and appropriate way to convey interest. And yes, tell the guy that you think he’s cute and smart and you’d like to see him again. Guys love having their ego stroked. Don’t let him do all the work on the date. Pull your weight, be interested in him!

    As to the issue of settling down….that is a big problem if you ask me unless you are dating guys in their 30s/40s. Guys in there 20s generally don’t want to settle down….even with a 10. So Ashley should modify her game plan if she is husband hunting in the late 20 something age group otherwise she will wind up routinely disappointed.

  9. 29

    Oh, please. Evan, I normally agree with what you say, but you were way off target on this one. I’m attractive, my sisters are attractive and I know a number of attractive women- ranging from cute to drop dead gorgeous. 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.

    1. 29.1


      I very much agree with your last sentence,   “If these women are single it’s for one of two reasons……”.



  10. 30

    I’m glad Ashley had the guts to write this, because it’s hard to wonder out loud if you’re being judged by your looks, because it sounds so … arrogant. Or pathetic — “yea, being gorgeous is such a drag.” But she’s telling the truth, and I sure don’t have any answers, but one thing that hasn’t been mentioned is that beautiful women were more than likely beautiful girls when they were young. And if you’re a “pretty girl,” you learn very early on that your looks are what gets the attention, makes you stand out from the rest, and unfortunately, what gives you value. No matter that you are also a genuinely good-hearted kid, who is kind and smart, a good athlete or teamplayer, or whatever other qualities you possess besides your physical beauty. You become an object for others to admire. How many times have you heard adults say, “Oh, she’s such a pretty girl. She’ll have to fight the men off when she gets older.” Then, when you’re older and actually are fighting off men and yet can’t find anyone to love you for you, you wonder what’s wrong with you. You were raised to believe that your looks were enough to carry the day. So you start wondering if maybe you ARE boring, or needy, or neurotic, have bad breath, etc. Sure, there are beautiful people who are shallow, boring or mean, just like there are less-than-beautiful people who are that way. And yes, looks are important & but only to a point, because if you haven’t also developed your own personality, character, sense of humor & convictions (because you weren’t encouraged to….. you learned your looks would be enough), it’s baffling as an adult to learn that looks are, in fact, not enough. People — particularly us women — assume that attractive women have it easy and are never lonely, just like we tend to assume that naturally thin women are happy, or they SHOULD be. Here’s what you hear: “Look at that waist. I hate her.” Or “Give me a break — could her teeth BE more perfect? God, I hate her.” I’m small and fairly attractive, so men have always assumed I’m cute, fun, harmless, and cuddly. And I am some of those things, some of the time, but when I’m just getting to know a guy and I open my mouth and say something like, “Hmm, I don’t agree with that,” men act like they’ve been betrayed, tricked, deceived. How dare I have a brain, an opinion? Well dang, I guess I’m just faux cute. My point is that people might be more aware of the comments and assumptions they make, especially around young girls, complimenting them on their prettiness as opposed to, for example, their great smile or radiant personality or kindness to their friends. Ashley, I doubt you’re boring or a bitch. Dating is just hard for everyone, and finding a connection takes work and patience, but it’s still worth examining the things that have been suggested above and see if they help. Best of luck.

    1. 30.1

      Sometimes we below average to average types would like to trade places with the beautiful/hot ones until we realize they don’t have it any better than we do. They just have a different set of issues.   

  11. 31

    Evan, and bloggers – this one hit home. At 50, single and very attractive, I have dated those who indeed are only after the thrill of dating a “10” – they only get one date – years of experience have helped me to see thru them. But, met someone a couple of months ago – he tells me how beautiful and smart I am, and fills my ego. Yes, I am insecure – never felt appreciated for more than just beauty – but I hide that insecurity very well. I can’t read him – goes from hot to cold – if I don’t respond to his voicemails, etc in a timely manner, his insecurities shine bright – thinking I am dating around, etc – I’m not. I don’t want to be with anyone but him right now, and have told him that. If I do timely respond, he acts like he has me wrapped around his little finger, and I don’t hear from him for a week or more. What’s up with this? Men I’ve dated have either been smothering or so aloof they can’t be ‘found’ … does this type of behavior have anything to do with my being attractive, and maybe his thinking every man out there secretly wants me, or that I want every man out there to prove I can have any man I want (which, I truly do not believe)… can someone please help me understand?? Trust me, natural beauty is a curse, not a blessing.

  12. 32

    “Then I’m over her house for one of the first times and I ask where her recyclables are. I don’t recycle. Just throw it in the trash. Done.”

    Gosh darn, Markus.

    No suggestions? No education? No patience?

    You trashed the relationship because she wouldn’t recycle one time.

    If a woman wrote in, “I stopped dating him because I was over at his house and he wouldn’t recycle once,” you’d be ALL OVER HER about how inflexible and rigid and harsh and unbending and unworthy of a decent guy she was.

    And you men accuse us women of being rigid.

    More directly OT, I hope the guys Ashley is dating aren’t grilling her on the first date on her recycling habits. Just because a beautiful woman might have one flaw, you all (figuratively) beat on her, pull her letter apart, and take her to task because of your own terrors of rejection — and then you tell us we have to be flexible and put up with ALL your BS.

    Hardly a balanced way of relating, I’d say.

    (And E, man – the little dig about “pretty girls having different problems than fat girls”? Gee, I hope Kate Dillon and Megan Garcia – and Whitney from the latest ANTM season, for that matter – aren’t telling their friends not to read you anymore.)

    I’ll let one of the other ladies deal with the guy (Mark?) who said, “Yeah, Ashley, we run away from you because you’re aloof.”

    She didn’t say she was aloof. She said she appeared aloof because she was shy. Not only did you misread her and give her no credit for attempting to be nice, you attempted to blame your own fears of rejection on her.


  13. 33

    Well said, Zann.
    I’m now wishing for an “edit” or “delete” button because I’m uncomfortable with the personal anecdotes that I posted.

  14. 34

    Steve: Picard — definitely Picard. 🙂

  15. 35

    I found Marcus’ little rant about recycling amusing.
    “If I think you’re not a good person I won’t be able to stand being around you.” Feels that strong about not recycling? Wow. Gotta wonder what some of the other dealbreakers are.

  16. 36

    Kristina May 22nd 2008 at 12:55 pm 29
    I’m attractive, my sisters are attractive and I know a number of attractive women- ranging from cute to drop dead gorgeous

    Kristinia. Please get in touch, ROFL 🙂

  17. 37

    [i]Shawna May 23rd 2008 at 09:19 am 34
    Steve: Picard definitely Picard. :)[/i]

    I only date women who are Kirk fans. Oh well, maybe we can still be friends 🙂

  18. 38

    to evan,

    Single, small waist, large breasted, blond, 40 something in L.A?…they are very, particular about the public place they go to…..if they get out at all….I can see why…LOL!..

  19. 39

    When I first started dating, I found two types of pretty girls–the first added intense attention to their hair, makup and clothes to their considerable beauty. The others were great looking but didn’t obviously obsess over their presentation.

    Personally I found the ones who spent much time on their appearance less interesting since they had less time to spend developing themselves and using surface presentation as a major part of presenting themselves was ultimately not that interesting. Having to regularly fight my way through the men who were interested in the look was more work than it was worth.

    The genuinely good/great looking were a different story. I found many had a hard time finding quality dates like the rest of us. Often tired of being “hit on” by guys looking for a ‘score’, being thoughtful and sincere was well received, though it often took longer to get their confidence.

    Ultimately, substance and compatibility always play well. Good looks and sex only get you so far in a relationship. In the end, it is just the two of you together. Being able to genuinely connect and having something interesting to talk about can carry you a lifetime.

  20. 40


    I stayed in the relationship for a bit after that and more red flags popped up anyway. If it was something that could’ve been easily remedied…fine. But I’m 39 and she was 41. It’s not like no one knows how or why to recycle. I’m not a training camp.


    I’m very concerned about the environment and am looking for some level of concern about same. Recycling is EASY. 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?

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