*This article is part of a series; I recommend reading Part One: A Modern Virgin and Part Two: What I Learned About Sex From An Older Man first. I’m welcoming feedback and contributions so please email me here.

Part Three: The Only One Night Stand That I Regret.
A friend of mine once said the only thing that prevents a man from getting laid is the woman before him. I laughed at the time, because I thought to myself it was true! I was sitting in front of him, laughing at his jokes and enjoying his intelligent banter. I was wearing phenomenally great underwear, beautiful perfume and everything that ought to have been waxed, tidied, buffed and moisturized had been. It was a collision amongst the stars – almost. I was the woman, sitting in front of him, very badly wanting him to ask me or kiss me or give me a chance to say ‘yes, let’s get naked’, – but I could not bring myself to tell him so. If only he’d asked, I would have said yes.

The truth was he had asked me, once before on the first night we met. He was slightly drunk at the time and I was too afraid to say yes then, in case he didn’t really mean it. Worse, I might find myself longing for that ongoing intimacy with a man who I barely knew. After all, the line between sex and love is pretty murky for me. I wanted something more than just getting the virginity thing done with. So, of course, it makes sense the only one night stand I regret, is the one I never had.

At this point, those of a spiritual nature will be starting to squirm. How can I, having been of such sound and strong spiritual belief be talking in this way? Good or bad, my spiritual experiences hadn’t (and still haven’t) answered where and how my sexuality plays into my life as an unmarried woman in my 30s. So by the time I was 31, I was largely questioning whether or not I should hold on to my virginity for the sake of it.

Since that first drunken invitation, I’ve learned he is an extraordinarily good man. He is intelligent, engaging, funny and generous with his friends. If I didn’t want to go home with him for lack of intimacy in the beginning, by the time I got to know him a little, it was enough to convince me that the next time he asked, I would say yes, without hesitation. He had become trustworthy.

When you are an older and independent virgin, you don’t worry about what your parents will think or whether or not you’ll get in trouble. Without a strict hierarchical church setting, there is no one to disappoint. It was simply my choice. I’d pretty much given up hope of meeting anyone within the faith communities that I was part of. Those who caught my attention didn’t seem interested in this larger-than-life, strong-minded individual or they lived too far away or worse (better) they were married already. So when you decide that maybe you’re up for losing your virginity after all, you have to start meeting people. Deciding to try to no longer be a virgin might seem a little extreme, but how else was I going to discover what I truly thought and felt about this without pushing out to an extreme?

Dating and Sex.
Dating outside the church walls becomes a pretty significant consideration, for obvious reasons. My view is that values matter as much, if not more than specific beliefs, so I have been open to dating outside the church anyway. But dating outside the church comes with different expectations and that’s where I became woefully insecure.

I was envious of women who could meet men online or in bars and fall effortlessly into bed. When online dating turned quickly into expectations of first date sleepovers or worse, when I told people too soon, my virginity became a flag for conquest. Other times it was the silent elephant in the room I was trying to ignore.

Sometimes when you tell people who don’t expect it of you, they look at you with pity. They can’t help it. It rushes over their face instantly. Sometimes they look at you with curiosity, a new puzzle to work out. Sometimes they just look at you with greed.

There are times and stages in our lives where sex outside of some sort of commitment or trusting relationship is undoubtedly harmful, particularly when we are young, or if one person is abusing another. Recognizing the difference between good sex and bad sex is important.

But could there be an in-between? Where two adults in a secure and trusting friendship can express themselves sexually? Famously, a dear friend of mine offered (slightly tipsy) to ‘de-flower’ me, but then retracted the offer saying, “I mean, it should be with someone you love, but…I’d do that for you.” I have had to consider that ‘friends with benefits’ might be a reasonable idea. Could it be a healthy form of sexual expression for two trusting adults?

I’ve been propositioned for phone sex, sexting, one night stands and a few other proclivities from time to time. Sometimes I’ve made good choices, other times I haven’t. There’s a vast amount to be learned about my own sexual taste and expression. Pornography, erotica and sex toys form the basis of many single women’s sex lives and I live in a world where managing a vibrant, demanding sexuality requires some diligence and responsibility. But I’ll write more about that later. I’ve shared a bed with a 23-year-old boy (accidentally) and felt no desire whatsoever. Sometimes I panic that I want too much, or that by the time I’m having sex in a great relationship, I’m going to run out of time before my body no longer wants to cooperate with me. It’s a really basic, human kind of thought but I think it all the time.

Here are some things I learned about myself.

  1. This may be the only area of my life where I’m actually not brave. Sure, I can write about it, but actually following through with a Tinder date, or an online invitation? Meeting someone for the express purpose of losing my virginity? I’m not brave enough for that. After all these years, I don’t trust the robustness of my self-esteem to follow through with it. I’m just afraid now of everything I don’t know, as well as what I do. I’m afraid about how far I’d be willing to go just to meet my desires, as well as how I might be self-sabotaging because of my lofty ideals.
  2. I don’t want sex without emotional intimacy.
    Part of me wants to be that brave and that liberal, but I’m a deeply romantic and philosophical creature. It’s the biggest turn-off ever to be told you want to sleep with me, but you don’t want a relationship with me. Like, you don’t even want to be friends?
  1. Speaking of trust, trust becomes the most important thing. In meeting people, I would think – are you trustworthy? Can I be this vulnerable with you? It’s not just being vulnerable of body, but also vulnerable with my story. After all, it’s not easy to say “I’m a virgin, would you mind helping me deal with that?” Trust in relationships is the most important thing. For me, it’s trust in the morning after. I’ve been learning a lot about this recently, the triggers around my own insecurities.
  1. Regardless of whether I’m in a sexual relationship, I have more insecurity to deal with if I want an intimate relationship. This is maybe the hardest part. When you think that you’re ready and capable of something only to learn that there’s a bunch more stuff to think about and deal with. Is this symptomatic of being an over-thinker? Yes, but that’s why I write the way I do. I think about people and relationships all the time. So
  1. I want the whole deal, healthy sexuality and relational intimacy. My backyard philosopher friend knew it long before I did, but I had to try it for myself in order to learn that I actually don’t want a meaningless sexual encounter. Does that mean I’d have sex with a friend I trusted and loved? Possibly yes, but I want to have sex in the context of real love. But even the suggestion of that reflects an expectation of a certain amount of trust and intimacy.

Thank God, I had my old friend’s voice in my ear. As earnest and heartfelt as my decision to no longer stay a virgin was, it didn’t matter. I went out and tested what my values really were and learned that I didn’t really want to sacrifice some things for other things. I found myself choosing not to settle for getting it over and done with. Also, it’s harder to get laid than you think. Men are often, far more gentlemanly than we give them credit for or I just find all the best ones.

My ideal is still to build trust and emotional intimacy with someone who accepts me (rejection is a strong theme in my history), is trustworthy and committed. I think that is something like what love looks like. Now I know that to be a virgin is a choice I’ve made, to choose to grow into love and to express that love, intimacy and trust through sex, really good, knee-knocking, spiritual sex. Somewhere in between the emotional intimacy and trust building is where sex happens, I think. Hopefully sooner, rather than later. It’s a risk, I know but I hope that it’s worth it.

And it’s not because the Bible said so, or because I’m religious. Those things are part of who I am, but I’ve also explored my sexuality and the fringes of how far I can go before it turns dark and separates from my soul a little bit. And I’ve come back from that place.

I’m no longer an accidental virgin. I’ve had the chance to have men in my bed and I’ve said no, because it wasn’t enough. I’d be using them as much as they’d be using me. For me, it’s not the way. Now, I’m a virgin by choice, until the time is right and I hope it’s soon. That’s a harder choice, I think, to intentionally choose to not have sex until the relationship is right. There’s no visible hope on the horizon that the meaningful, intimate relationship I long for is around the corner, so it’s a bloody tough choice.