The Virgin Diaries: My Complicated Relationship with Sex

photo by woodleywonderworks

Our contributor Katherine Chen, who is a sophomore 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 sixth installment:

When I first got my period, my mother wanted to avoid the dreaded “Talk” but still convey the fact that I was now capable of being impregnated, so she purchased a number of instructional books that explained how menstruation was actually a natural process and not the product of some disability or mutation. Surprisingly, the topics covered in these books were not confined to anatomy and the scientific mechanics of fertility. A few of them contained quite a healthy bit of sex, too. Well, maybe “healthy” is the wrong choice of words.

I distinctly remember reading about the story of one teenage girl who decides, perhaps against her better judgment, to sneak out of her bedroom in the dead of night and meet up with every parent’s nightmare: the bad boy. A few pages later, this boyfriend attempts to date rape the girl in the back of his car by shoving his hand between her legs, but she manages to escape. My feelings at the time were a combination of dread, fear, excitement, and interest.

Looking back, this one story fueled what would become my complicated fascination with and relationship to all things sex. While it turned me on (probably because it was the first “sex scene” I’d ever been exposed to), it also taught me certain gender roles, however misguided: guys want it, girls don’t; guys are aggressive, girls are submissive. It’s probably one of the reasons why I’ve been sitting on the sidelines when it comes to actively pursuing sexual partners today. But it’s also one of the reasons I admire certain female porn stars: they always look like they’re having fun and are on top of things (literally) instead of being controlled.

And while that story drove home the lesson that sex was dangerous, it also made me hyper-aware of the widespread occurrence of sex in everyday life. I started seeing it everywhere. Imagine my amusement when a high school English teacher suggested that the cross was a phallic symbol and that the scene in the movie-version of “Hamlet” where Mel Gibson points his sword at his mother’s breast contained strong sexual overtones. Everything, even the absence of sex (for example, when sexual desire is sublimated for a “higher” purpose), could still be explained through sex. This notion transformed libido, at least in my mind, into a truly powerful force with no boundaries, something that is both awe-inspiring and scary.

For better or for worse, my over-analysis of sex has raised my views to such black-and-white extremes that I can no longer reconcile my true feelings about sex in relation to myself. While I have not yet been in a relationship where I seriously considered the prospect of having sex, even if I had been, I doubt I would have known what I wanted to do. On the one hand, having seen all the good that can come from sex, I have placed it on such a high pedestal that if and when I  do engage in sexual intercourse with a partner, I fear it will inevitably be disappointing.  On the other hand, having also seen all  the bad that can come from sex, I am absolutely terrified by its potential consequences, such as the transmission of diseases,  unwanted pregnancy and heartbreak. And once I’ve had it, I’m most afraid of losing my outsider’s perspective — I’ll be forever comparing and contrasting my own personal experience with others, which seems like it would be more limiting than liberating.

In the end, I am grateful for my outsider view of sex, and thankful for the fact that I am not yet one of the initiated, if only to prevent myself from getting hurt or disillusioned about something I have built up to “heavenly” proportions. This may come across as contradictory for someone who has just admitted to being fascinated by sex, but I do not believe that I am such an outsider that I cannot understand the important role sex plays in all forms artistic, musical, spiritual, religious and even scientific. Plus, spending all this time thinking about sex enables me to understand better my own opinions about this confusing topic. So until the time comes when I feel confident enough to step outside of my box, writing and reading about sex will do just fine.


  1. I don’t think this dichotomy of attitudes towards sex is limited to virgins, or to people with limited sexual experience. There’s so much conflicting information from the media, from porn, from religious institutions about what constitutes ‘good’ sex that it’s hard for anyone to form a healthy opinion towards sex and relationships, whether or not they are in a relationship and/or sexually active.

  2. I was a virgin when I got married at 22. I’m now 28 and just now hitting my sexual stride and I can tell you this, the first time will be uncomfortable at first, but you can learn pretty fast how to make things go better if you can actually get out of your head.

    My biggest problem for the longest time was worrying too much about what my husband wanted/needed and not focusing on what felt good for me. The truth is that the more I focus on what feels good for me, the hotter and more intense it is for my husband. He gets turned on by how “into it” I am and he himself stops worrying about getting me off. The best thing for us both has been to completely let go of our inhibitions- which is something entirely foreign to both of us. We both were raised as extremely conservative Christians (his parents bordering on fundamentalist) and our backgrounds seemed to cause a lot of expectations that were damaging to our level of intimacy because we were too afraid of ‘letting go’ and doing things that might be skewed as inappropriate or morally wrong.

    What we’ve truly learned is that our marriage in our minds has to entitle us to be intimate how we see fit, which includes trying a variety of positions, a lot of naughty lingerie, sexy photos, talking about our dirty fantasies and acting on some of them together.

    My biggest piece of advice to you is be open with your partner and tell them what feels good, or what you want them to do to you…whether they are a long or short-term partner- it really doesn’t matter. Letting a partner into your thought life is just about as sexy as any physical act you do together and can play a huge part in how successful your attempt at intimacy is.

  3. As a soon-to-be married, 27-year-old virgin, I can tell you that I think you are correct in most cases you presented, and I enjoyed reading your article. Choosing to be informed is the most important thing out there. Choosing not to compare your future partner to anyone else is a gift that can only be given once. Some people think that virgins are just scared of having intercourse. It’s not true–they just place sex aside until they feel they are ready to explore the topic with someone that they trust. For me, it means that I want to be married first–I only want to share this part of my life with my husband. For others, it may be different, but that is ok because everyone is different by nature.

    I have a friend that told me that I’m insane to wait–‘be sure you check that shit out’ she said to me–but I think her own track record speaks for itself as she’s unhappily single. I’ll take being married, virgin, and happy over being single, sexually active, and unhappy. That’s not to say that all single and sexually active people are unhappy… but I’ve yet to meet a happy one, most are whinging about how they didn’t like how their bf didn’t do this or that right, etc… Married people can only complain to each other and work it out–they signed up knowing what they were getting into.

    Wow, that turned into a rant about marriage, sorry, but I don’t have the heart to delete it.

  4. I am a 22 year old virgin who hasn’t even officially dated. I’ve only kind of gone out with guys who were already friends, then usually once it got to a certain point I would panic and backpedal quickly into friendship. It isn’t so much that I am afraid of sex, but afraid that I’ll be horribly awkward about it. I also feel that I am too awkward to date someone I don’t already know. And it definitely is getting more and more difficult to explain that I’ve never really had a relationship.

    The one thing is that I do masturbate and I feel comfortable with my own body, which helps a lot. Knowing that I don’t have to depend on a man to get off is very liberating, and I now get much better orgasms than when I first started masturbating.

    I recently met a guy in his 30s who I really like and we’ve been flirting a lot (non-awkwardly). He asked me out, but we are both too busy to go out for at least a couple of weeks, which partly made it easier for me to say yes than a more immediate date. But now I am dreading the awkwardness of a date. We really only have time to flirt for maybe 15 minutes at a time. I don’t know how to make the conversation last through an entire date, especially since we have very different backgrounds, even without the age difference. I also think I am falling into my personal pattern of leaving relationships before they can really begin.

  5. As a 30 year old virgin with essentially the same outlook as Katherine, I do appreciate the column. As a reader of science, columns like Em and Lo, and romance novels, my fear is that my view of sex has become too clinical, too objective. I wouldn’t say I idealize the experience or expect anything mind-blowing. And I certainly don’t depend on anyone else for sexual gratification.

    At the same time, the older you get, the complicated it becomes to explain your virginity to others. Yes, if that’s going to be a turn-off for a guy, you’re better off without him. However, there seems to be a supposition among many (one guy actually verbalized this to me) that if a girl has her first sexual experience, she will become instantly clingy and emotionally overwrought.

    What it comes down to is that, given the fact that first-time sex isn’t all roses and rainbows, wouldn’t I want to choose the best possible scenario and have a partner that is kind and considerate and at least as interested in my pleasure (if not more) than his own?

    This isn’t a “wait for marriage” spiel. I don’t plan to wait. Nor is it a diatribe against anyone who has been sexually active from any given age. More a reply that there are more reasons than the default one for putting off that decision.

  6. Yes, it’s going to be “disappointing” the first time, I can pretty much guarantee it. No, it will not be as consequential as you think, however, if you are thoughtful, sober and use protection and trust the person you are with, it will be worth the effort and the facing of your Fears and will cause much maturing and expanding of your outlook, not to mention your expectations for the future.

    All men are NOT predators, and a woman can and should have just as much control during sex (even her first time) as the man does. Your fears are understandable (I had the same ones, until I was about 14 or so) but of the type of which only experience will show you just how far fetched those fears were. Likewise your expectations.

    The longer you “wait” the more the fantasy will grow and the MORE the disappointment will be a given. Sex is a normal behavior, which requires a learning curve.

    I know of no woman (and few men) who had mind blowing sex the first time. Nice? Yeah, but if you blow it out of proportion, when you don’t know what is involved in the actual act, it will seem all the more disappointing when it does happen. Have expectations, but realistic ones.

    “Finding the right guy” is no guarantee of multiple orgasms, fireworks going off, and ultimate pleasure and Seeing the Face of (your favorite deity here) the minute your cherry is popped. In fact, expecting that will only cause you to maybe blame him, when it was all (well, mostly) your irrational expectation in the first place. This “waiting” and the irrational expectation is doing in your first sexual relationship before it even occurs.

    If you aren’t ready (really?) then, OK, but don’t stay away from the pleasure and ecstasy and maturity of sex, just so you can stay “an outsider” so you can write a column or a blog. That makes absolutely no sense.

  7. I completely agree. I’m just like that about sex (and I am soon to be a sophomore). Its fabulous to know I’m not alone in how I think. You’re literally the first person I have found who thinks like I do. Its very reassuring.

  8. Thank you Katherine.
    As a fellow virgin it was so nice to see that I am not alone in my contradictory feelings towards sex. I especially appreciated how eloquently you explained the dichotomy. Next time someone asks me why I haven’t had sex, I’m going to hand them your article.

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