How Can a Shy Woman with A Sexy Job Find the Right Guy?

How Can a Shy Woman with A Sexy Job Find the Right Guy

I should start by saying I read your article about attractive women having a hard time dating – and while I relate to that, I feel the answer of “be vulnerable and trust people” is wonderful but not enough.

I have an unusual job – I work at a bikini bar and am a professional motorcycle rider. Men assume I am a party animal, or superficial but that’s not the case at all. I’m a softy and a nature person, and I am only interested in healthy monogamous relationships. Most people would not assume I was an ugly duckling the majority of my life– and finding love was a lot easier back when.

Mistreatment is making me into a shy person and my friends in this industry, and I, all deal with the same problem: it seems our looks and jobs don’t match our actual personalities.

So here is my problem/ question: I am not attracted to the nice men that like me because they tend to be so intimidated by me. The sleazy guys give up fast because they realize I am not what they are looking for. When I approach men, they tend to be rude to me and blatantly brush me off…like being bullied in Jr. High. This doesn’t help my shyness.

This wasn’t a problem when I was an out-of-shape waitress.

What’s the solution for nice women with sexy jobs?


Gotta give you credit, Charlie. I’ve never gotten a question like this, and I’m rarely tongue-tied when it comes to delivering a measured response. I’m reminded of a letter from an urban hipster who hung around with a bunch of skateboarding artists and wondered why it was so hard for her to find love. If I recall, I told her that skateboarding artists are, in general, not the most emotionally or financially stable people around, and that she should consider expanding her search beyond her chosen community.

I think I’d offer you much of the same advice.

I know my own biases. I’m a clean-cut guy who has no tattoos and is afraid of motorcycles (sorry, but the injury risk is REALLY high!) I do my best to be non-judgmental, but I fail sometimes.

One of the perils of this job is that you’re forced to rely on generalizations and stereotypes. There’s no way around it, unless you want to deny reality. It’s not that stereotypes are always true, it’s that they’re often true — which is why people rely on them so frequently. Statistics bear these stereotypes out.

In general, men are taller than women. Some women are taller. Most are not. That’s not an opinion.

In general, Asians get good grades. That doesn’t mean many white, black and Hispanic people don’t get good grades or that there aren’t some Asians who flunk out of school. But if you look at Asians on top college campuses, you can see they’re disproportionately represented compared to the general population.

It’s not that stereotypes are always true, it’s that they’re often true — which is why people rely on them so frequently.

I know this is a big tangent, but it’s an important one. Chances are, someone’s already gotten mad at the fact that I said that artists are not as emotionally or financially stable as other people. Again, that’s not my opinion. From Jonah Lehrer’s “Imagine”:

“Andreasen found that 80 of writers (in the Iowa Writers’ Workshop in the early 1980’s) met the formal diagnostic criteria for some type of depression. She also found that nearly 40 percent of the successful creative people she investigated had bipolar disorder, a rate that’s approximately twenty times higher than it is in the general population. More recently, the psychiatrist Hagop Akiskal found that nearly two-thirds of a sample of influential European artists were bipolar.”

Is it any surprise that (some) creative artists are more likely to suffer from depression — not just because of their artistic temperament, but because of the financial instability of their career choices? I don’t think so. Hell, I was never more depressed than I was in my 20’s when I was trying to make a living selling screenplays and had to support myself with odd jobs for 25K/year.

So when I say that artists aren’t always great bets as romantic partners, understand: it’s not an attack on artists; it’s an observation based on numerous studies.

Without having any studies handy, what observations would you have about bikini bar culture and motorcycle culture?

I don’t judge you, I empathize with you, and I hope you find a nice guy (with a little edge) who wants the same things you do out of life.

Rebellious. Going against the grain. Valuing personal freedom over conventional norms. Not giving a shit about what the mainstream thinks. Risk-taking. Lots of risk-taking.

No desk jobs. No shirts. No cars. Bikini/biker culture is not one for such conformity. In general.

That’s right. I’m not attacking every single bikini/biker on Planet Earth. I’m using shorthand heuristics to point out that perhaps bikini bars aren’t the optimal culture for a nice girl who wants to settle down.

This doesn’t mean you must quit your job to find love. Nor does it mean you have to disavow your bikini/biker friends. It does mean, however, that you may need to expand your dating circles a bit — and also do one very important thing:

The same way you wouldn’t want me to assume all bikini/bikers are the same, don’t assume that all “nice men” are equally intimidated by you.

    a) It’s not true. You haven’t met every nice man on the planet. Plus, it only takes one.

    b) A lot of nice guys may not be intimidated by you, but they may be turned off by your job and culture. Same way I’d guess a lot of biker chicks would turned off by vanilla guys like me.

I would probably suggest dating online — writing a great profile, forgoing the biker/bikini pics for a more mainstream look, leaving out your job title — and making a connection based on something other than what you have in common on paper.

You are entitled to say that you don’t want to deny this part of yourself. But your bikini/biker persona is likely to attract two main types: biker guys and guys who want to just get laid. Pick your poison.

Either way, I hope it’s clear: I don’t judge you, I empathize with you, and I hope you find a nice guy (with a little edge) who wants the same things you do out of life. I trust you will.

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  1. 1

    This article is a very good advice to single women with high profile jobs and high net worth

  2. 2
    Joseph Hogue

    Girls this is for you.   Specially for the ones who are looking for a great  soul mate. Being ambitious in life is good but you should also think of your partner’s choice.

  3. 3

    Hi Charlie,

    __In high school I knew 4 girls who after graduation ended up as bikini models for car shows. Two of them were the prettiest girls in school, and the other two were ugly ducklings during high school.

    __Except… they were NOT ugly; but they did like most of us did in high school (and now) they compared themselves to the prettiest, most popular girls.

    __Anyway, the attention got to all four of their heads and they unconsciously became very picky about the men they dated, even though outwardly they would always claim they wanted a good guy with balls.

    __Also, I think the other two girls were trying their hardest to keep up with the prettiest two, in some kind of twisted, I am just as desirable and sexy as them mentality. So they only went after the hottest guys who were use to getting a lot of female attention from an early age so, experience-wise, these men were out of their leagues.

    __The biggest difference was that the two prettier girls dealt with the men from a position of confidence, while the two who felt they were ducklings that transformed into swans dealt with the men from a position of anger and Over-compensation (check out Evan’s post on the woman who resented the men who started to give her attention after she lost a lot of weight).

    __Now the two prettiest are married, one of the self-proclaimed ugly ducklings is married and one is still single. The reason one self-proclaimed duckling is married and the other isn’t is because the one went to college, did a lot of things with her life that did not depend upon her beauty but her intelligence and character, which -in my opinion-made her a more emotionally secure and confident person. The other, to this day she still blames men for being intimidated by her job and looks, instead of realizing that she has serious personality issues.

    …    …    …

    __Now after that long story, my point is, your job is fine, just focus on better quality men. However, make sure that YOU are choosing these men from a position of confidence and not neediness or out of some unconscious desire to prove your self-worth because you got a super hot guy that other women want to date you.

  4. 4
    Joseph Hogue

    I think women are smart enough to find the right partner for them, and the ones with sexy jobs might be smarter!

  5. 5

    How does a self-described “shy” girl end up with a bikini-waitress job (if i understood the job description correctly). This is so incongruent, now wonder men are confused around her.

    1. 5.1

      I can’t answer to that specifically, but I can answer in another way. I’m an actor. I love the feeling of pretending to be someone else, I also love being on stage and having all eyes on me. But only as a character. In real life I’m pretty shy, and when I’m not pretending to be someone can be quite awkward and unsure how I’m supposed to be. Getting to hide behind a character, getting to be outgoing and get attention and all the things more popular extroverted people get is a wonderful feeling. And that’s one of the reasons I enjoy doing it.

      I think the same can be said of people who work at those kinds of jobs. I think if they feel good about how they look and are happy showing that off that they can put on a fun character and get to play act at being not shy. The role of “bikini waitress” as it were. It allows the person to feel excited and the centre of attention without actually having to worry about what others are thinking etc. When you are a waitress at such a place you know the guys will think you’re hot, you know the right kind of banter, you know what your job is. Real life though? There are no rules. And being yourself? That can be scary and vulnerable.

      So that’s what it likely is about. The chance to live a life that isn’t really you and hide behind a character. But it doesn’t mean you want to be that all the time, and it doesn’t mean you aren’t insecure also.

      While I do understand why people, men and women alike, might not understand this I do find it a little strange at the same time they don’t. I think a lot of people put on personas to survive the world, I think a lot of people long to be loved for who they are and not how they appear to be. I think it’s a daily struggle for so many. Who am I really? Who do I want to be? Who do I wish I was? The idea that someone who dresses sexy is therefore always confident and outgoing to me is as odd as someone who would say that someone who is conservative and quiet never wants to have a good time or be sexy. We are multifaceted humans, and if we got to know each other more as individuals and less as “types” I think it would help us all immeasurably. I do wish we’d stop making assumptions before getting to know people. And just, you know, get to know them.

  6. 6

    Hi Charlie,

    Evan touched on the issue of the role stereotyping may play in your difficulties finding men.

    “Without having any studies handy, what observations would you have about bikini bar culture and motorcycle culture?”

    “Rebellious. Going against the grain. Valuing personal freedom over conventional norms. Not giving a shit about what the mainstream thinks. Risk-taking. Lots of risk-taking.”

    To expand upon that, because one of your jobs involves displaying your sexuality, you also my be having difficulty with some men because of persistent sexual double standards and the male madonna-whore split.   Unfortunately, some men might see or hear what you do for a living and they may automatically stereotype you as sexually easy, a fast girl, or a slut, and not take you seriously as relationship material.

    In college I knew a few girls who were very smart, sensible, and easygoing who worked as cocktail waitresses, lingerie/bikini models, or strippers.   They said that often times, guys they met, who knew what they did for work on initially meeting, would see them as just a body and not take them seriously. They would never go out with men they met on the job because of this.   To try and compensate for this effect, when they met a new guy they  were interested in, they usually initially told him that they were waitresses, did some modeling, or were bar servers.   If things started going somewhere, they would then clarify exactly what their jobs involved.   The guys almost always understood why the women were vague on the job specifics when they first met.   None of these girls were ashamed of their jobs, they were just dealing with some of the unpleasant realities of life and love.

  7. 7

    A friend of mine who is a diplomat downplays her job role because men are instantly intimidated by the job title. I avoid stating what i do for as long as possible (i am an executive assistant) as dates can think that i am subservient (hah!), slightly dim (no comment) or have no ambition (studying towards my Psychology bachelor and am just as ambitious as my non-secretarial colleagues).

    These are just a few examples. I have learnt through my own experiences that you are far more than just your job title, but that people feel the need to box you into a certain role, based on the job you happened to wander into. I see why. When we are dating we want to know as quickly as possible with what kind of person we are dealing with. We think that because a person has a certain kind of job, he or she fits a certain stereotype. We can breathe a sigh of relief as now we know who we are dealing with. The reality is that we can be a completely different person outside the workplace and would like to be appreciated in all our complexity. The only problem is that person at the other end of the table hasn’t had the chance to see all the different facets of you.

    In order to give them a chance to do that you can have a neutral job title on your profile that fits your current role. My diplomat friend is a project manager for example. It covers what she actually does but doesn’t have any connotations whatsoever.

    1. 7.1
      Lily in NYC

      Was it necessary to imply that executive assistants aren’t ambitious?   I’m an EA with an advanced degree who makes 6 figures in NYC.   Just like it probably bugs you to hear people say that  psych is a major chosen by mediocre students, it bugs me to hear stereotypes  about my chosen career.

  8. 8

    I had a bit of an epiphany about two years ago regarding this very subject. My whole life I was driven, strong, etc etc. I started my first company at 24 and am the stereotype of California girl by appearances. Behind the big hair and boobs, I am very shy, sometimes painfully so. I am very good at hiding it and people usually misconstrue me as stuck up and materialistic. In reality, I am the polar opposite.

    Having said this, I realized this “CEO” is actually a submissive. I am a giver and pleaser. Who Knew? I had spent my time with the wrong men. I needed and wanted a strong man because any other guy I cannot seem to respect enough to be in a relationship with. I believe a good relationship is about balance and I was with guys who were intimidated therefore became weak and submissive. They were stealing my role which created conflict and unhappiness for me.

    It happened by accident but I did meet someone and he was the first man who ever stood up to me. I never understood it, I am very quiet and I am all of 5’2″ so how could I be so intimidating to men? Now I get it and I am totally ok being who and what I am and I know exactly what I don’t want in my life…a weak man.

    Bottom line…the right guy will not be intimidated 🙂

  9. 9

    the most good man are the every day working man with a basic income thy are commited and dedicated loving like myself and most of all a one womans man dont look around and respect there wives and love them

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