The Virgin Diaries: Dating Downers

photo by Orin_Zebest

Our contributor Katherine Chen, who is a junior English major at Princeton University (check out her personal site here), is penning a series of confessions for EMandLO.com collectively called “The Virgin Diaries.” Here’s her seventh installment:

A few months ago, I was interviewing a relationship doctor for an online women’s magazine I was then contributing to. The doctor, who was leading a series of private workshops in New York City for single women, claimed her advice applied universally to “all women, every woman.” The first tidbit she offered was that women should always dress femininely on dates, especially the first one. Men, she asserted over the telephone with a slight click of her tongue, do not want to see a woman wearing pants on any romantic occasion. “Wear a skirt or just a dress!” she said, and after a short pause in which I was busy jotting down notes, she added, “with some jewelry and makeup. You can’t forget the makeup.”

Though the interview ended on a positive note, I hung up the phone feeling pangs of dismay and dread. According to this doctor, women who wore high heels, powdered their faces, and sprayed on chock loads of floral perfume were more likely to get hitched than women who, well, did none of the above. Of course, I fall into the latter category, with my loose t-shirts (most of which are attained at free giveaway events and school occasions), comfortable jeans, and old sneakers. I haven’t worn makeup since the eighth grade prom, and incidentally, feel less confident with makeup on than without. I dislike standing in front of the mirror for too long, and while I consider my appearance well-kept and clean, I am no Carrie Bradshaw. No, not even a Miranda Hobbes.

In addition to the out-of-character fashion statements the good doctor would have me make, she recommended flirty behavior, which has never come naturally to me. And then there was the concept of “actively seeking.” She insisted on having an assertive attitude and going out to as many bars and clubs as humanly possible to find a mate. Her logic was: the more dates you go on, the likelier it will be for you to find the perfect match. This meant stepping outside of your comfort zone, striking up conversations with strangers, and putting yourself on the line for flat-out rejection.

It was this third and final “seeking” tip that really brought back the agonizing memories from my high school days. When I was a junior, I had this huge crush on a senior who had just broken up with his childhood sweetheart. My friends encouraged me to take the first step in the relationship, which I did. Since he lived only three or four streets away from me, I innocently asked him if he would like to take a walk. We were always able to hold semi-long conversations at school, so I just assumed this would transfer naturally outside of the classroom. In short, it did not. He said something along the lines of, “I’m not sure what we would talk about while walking,” which quickly and definitively ended any hope of a relationship. He also had a friend of a friend inform me that he was uninterested in pursuing any kind of romantic relationship with me, just in case I hadn’t gotten the message already.

I didn’t give up on seeking out connections, though — not immediately, at least. On not one, but two more occasions did a boy I liked instruct his best friend to deliver the bad news, so as “not to hurt my feelings.” One young man decided to elude me by ducking behind a crowd whenever I passed him in the hallway. Another actually laughed in my face. After about the sixth instance of outright rejection, I gave up on dating entirely.

And talking with this doctor only confirmed my belief that the dating scene is just not for me. Why would I want to pretend to be someone I’m not? Why would I want to experience those painful rejections all over again? Especially from guys I’m not even sure I’m that into (which turned out to be the case in high school, considering how fairly quickly I was able to get over those six rejections). I don’t even really like the person I become when I’m dating someone: in the (very) few instances this has happened, I’ve lost sight of myself and my own interests. For example, a few years ago, when I started dating a Star Wars geek, I spent hours online, scanning Wikipedia pages, memorizing names, rewatching the movies, and trying to figure out the difference between Jango Fett and Boba Fett. I even wrote a few Fan Fiction-esque romance stories with Star Wars themes to impress the object of my affection. Unsurprisingly, all these efforts crashed and burned in the end when he discovered his Princess Leia somewhere else.

As alienated as I feel from the dating world, I still have fantasies of one day finding the perfect partner. This has, however, become such a remote concept over time that I wonder when, if ever, I will jump back into the dating world. In many ways, dating has become like sex to me: not only is it nonexistent in my life right now, but I have also built it up to such great heights that I’m terrified of being disappointed. I have no doubt in my mind that the longer I put it off, the harder it will be to jump back into the swing of things. But for now, it just seems easier, safer and a lot more comfortable to be an inactive seeker — in both departments.


  1. Better advice would be, be the best version of the real you.. I remember making a conscious decision on my very first date age 14 not to wear makeup, because i knew i wouldn’t want to always wear it every day, we were together 6 years so i guess it wasn’t a problem ;0) dresses and heels are me so to look like the best version of normal me i wear them, but make up is a once in a blue moon thing for parties and clubbing so there’s no point giving the impression that I will always look like that ;0)

  2. I really enjoyed this series, I started it with some trepidation (very judgmentally) assuming it would be filled with sanctimonious platitudes about modern morals. I couldn’t have been more wrong, such articulate and considered writing!

  3. Sometimes an accessory will change how people interact with you. A positive feedback loop happens: you get a compliment on the pretty XYZ (flower in your hair, colorful scarf, etc) and you feel more confident which then brings more positivity your way. I wear alot of black because I am comfortable in black, but I have alot of scarves so people don’t think I’m all doom.

    Another 2 things that turned it all around for me:
    1. Know what you want. It doesn’t sound like you want a relationship because of how it changes you. I get that, sister. Maybe you want more of a FWB NSA thing. If this is the case and you are upfront about it, guys will flock to you & even be respectful because they don’t have to worry about leading you on or running away.

    2. In conjunction with #1: okcupid.com. Great site if you are not wanting to go to bars where mini skirts, heels and low cut shirts are de riguer.

    Thanks for sharing.

  4. I think you’re right here Katherine – tarting yourself up like you’re Hannah Housewife is not cool if that’s not what you’re into. You’ll spend your whole date feeling ill at ease; even if it did go further, what next – do you keep wearing dresses to fit in with the image the guy felt attracted to, or be yourself and risk having wasted your time on someone who isn’t suited to the way you live your life?

    I like wearing dresses and make-up – that’s fine, and it’s up to me. If you like wearing jeans and sneakers, that’s fine and up to you. It’s always, ALWAYS better to be yourself and feel comfortable than try to be someone you’re not. If you try to start a relationship when you aren’t fairly sure of who you are, in my experience you end up losing too much of yourself meeting someone else’s expectations. Sure, be willing to compromise, but there’s a difference between trying something new for a change and completely overhauling yourself so Some Guy Might Like You.

    If you’re still not sure, then what might be a good idea for you is to experiment a bit – not Laura Ashley and caked-on make-up, but maybe keep a special pair of jeans and a nice top that suits you and makes you feel good, just for dates or nights out. Don’t go on the pull in bars and clubs – instead try chatting casually to guys in everyday situations and see what develops. My best relationships and one-night stands have all invariably begun with conversations first – often when I’m dressed in jeans and wearing faded, smudged or no make-up.

    Guys do tend to judge girls on their appearances, it’s true – but then we’re lucky that not all guys find the exact same things attractive. Figure out your own style, highlight your best points however you can, and then sit back comfortably laugh your ass off at the girls who are standing uncomfortably in too-high heels with their arms folded over too-low-cut tops, thinking they somehow look sexy. Confidence and ease of manner is sexy. Too much makeup is not.

  5. While I don’t subscribe to all of the advice the woman you talked to said, I do think that taking a little more pride in your appearance can really help in the dating realm. It sounds like you’re lacking self-confidence and sometimes that can be traced back to how you feel about your appearance. So step out on a limb, try something you normally wouldn’t, but don’t do it on a first date. Start applying it to your everyday life.

    I was a painfully shy and socially awkward geek in middle and high school and only in college when I learned that I had to step out of my comfort zone and make myself available did everything (including my confidence) fall into place. And the more confident I felt about myself, even though I was really doing it more for myself…the easier it was to attract guys. The easier it was to date. That’s not to say that I didn’t have some really terrible dates…or some guys that I wish I’d never known (i.e. stalked for 2 years by the first guy I ever dated), but I can tell you that I’m a better person for all of it.

    Another thing to remember. Changing your appearance doesn’t change the fabric of who you are as a person. But sometimes it can open doors for people to look past the shell and appreciate who you are when your appearance before had unknowingly been an emotional wall you’d put up to keep people out.

  6. ^ Again, image OR substance, as though they’re mutually exclusive. They’re not. Attractive packages can contain substance too. Be the total package.

  7. The doctor is full of it, and Johnny sounds like he’s more into image than substance.

    Not all of us are good at dating, as your own testimony confirms. Most of the guys I know can commiserate with your history as we all went through those experiences. It’s far more common than you think.

    I wouldn’t be surprised to see that your best prospects are right under your nose, maybe literally. You just haven’t seen them yet. Once you do (maybe with a friend’s assistance), you will know what to do.

  8. Yeah, I’ve never dated a girl who followed most of those pieces of advice… and none of the girls I’ve dated have ever had trouble finding guys, when they wanted to. It’s more an issue of what social group or ‘scene’ you’re looking in. If you’re hanging around in bars looking for people, maybe that applies, I can’t say for sure – perhaps the folks there prefer a more traditional approach – but we’ve all been gamers or eclectics of one sort or another, and the social expectations are different.

  9. I’m not saying NOT to take pride in your appearance, I’m saying you should do what comes natural. If you’re not a skirt wearing kind of girl, don’t wear one on a first date. You’ll feel uncomfortable and out of sorts, and that’s always unattractive.

    Just be you. If a particular guy dosen’t like that he can suck it up. There is no person worth compromising yourself for. And if you decide to try and fake it you’ll only find unsatisfying relationships.

  10. Yes listen to Johnny.

    If you can be that lax about your appearance AND still attract the opposite sex, Sarah, congratulations. You’re one in a hundred or less. For those of us who weren’t born hot, a little effort goes a long way.

    Helena Rubinstein once said, “there are no ugly women, only lazy ones.” Taking pride in your appearance and being laid-back and easy-going aren’t mutually exclusive. You can be both.

    I’m going to take a wild guess, Sarah: you’re in college or younger. That’s the last time that most people can hook up despite putting in a half-assed effort. Once graduate and you’re no longer constantly surrounded by horny young men with tons of free time, that usually won’t work anymore. But like I said, wild guess. Maybe you are once again the exception to the rule.

    OP, you could sit around hoping to become the exception. You could wait for Fortuna to spin a great guy your way. But waiting is slow and boring. It sounds like you’re getting fed up with it.

    Just try what Dr. Love recommends. If you REALLY hate it you can go right back to the Sarah camp.

  11. Don’t listen to Johnny.

    I don’t dress up, I don’t wear make-up, I don’t shave, I don’t visit bars, and yet I am able to find plenty of men who want to sleep with and date me.

    There are men out there who want a laid back, easy going woman. And they’re not going to have much patience for someone who looks high-maintenance and made-up on the first date. There are people who will love you for you, and they are worth waiting for.

    Of course, I do think it’s a bad idea to let your high school failure get in the way of future successes! Everyone gets rejected in humiliating and painful ways in high school. Don’t worry about, move on and still be open to more possibilities!

  12. The good doctor is absolutely right on all counts.

    Might I hypothesize that insecurity is behind your discomfort with this advice? She’s recommending stuff that you’re not used to, and that’s always tough to overcome. I don’t think of it as “being someone you’re not.” I hate to say it, but that’s so often a cop-out. People say that when they don’t want to step up.

    The doctor isn’t suggesting that you sleep around, or put on a sham act. She’s suggesting that you step it up in areas where you, ahem, might be a little bit lacking. I think if you followed her advice, and found that it works, you’d be entirely more comfortable with it.

    And that advice DOES work. I know because I followed it with spectacular results. Not the part about wearing heels and makeup – I mean the dude version of this advice.

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