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.

Say Something

12 Comments on "The Virgin Diaries: Dating Downers"

Sort by:   newest | oldest | most voted
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… Read more »

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!

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… Read more »
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… Read more »
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… Read more »

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


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.