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Dear Life., Guest Posts, Sex, Sexuality

Dear Life: I’ve Never Been Laid. Seeking Advice!

April 8, 2015

beauty-hunting-jen-logo-black1-300x88Welcome to Dear Life: An Unconventional Advice Column.

Your questions get sent to various authors from around the world to answer (and please keep sending because I have like 567 writers that want to answer your burning questions. Click here to  Email dearlife@jenniferpastiloff.com to submit a letter. Please make it as detailed as possible) Different writers offer their input when it comes to navigating through life’s messiness. We are “making messy okay.” Today’s letter is answered by author Emily Kramer, whom I had the pleasure of meeting when she attended the Writing & The Body Retreat I led with Lidia Yuknavitch. This is the second take on this letter by a different author than last time. The first one went viral (Read it here.) Hot topic, I guess!

Send us your questions because there loads of crazy authors waiting to answer ‘em. Just kidding, they aren’t crazy. 

Well okay, maybe a little. Aren’t we all? xo, Jen Pastiloff, Crazy Beauty Hunter

See you at a workshop/retreat soon!! xo 


Dear Life,

I am a 34 year old virgin.

I have no conservative religious beliefs and I’m not steadfastly “saving myself” for marriage. I just haven’t had sex….ever.

I have spent my life lying to the world, and myself, pretending to be something I’m not….or, more accurately, pretending to have done something I haven’t. People just assume that I’ve had sex and so I haven’t bothered to correct them. I feel like a fraud and a liar and so disconnected from one of life’s most basic human experiences. Stronger still are the feelings of shame and embarrassment and feeling like I’ve not only missed the boat, but am nowhere even near the water to have any hope of getting on board.

“BUT I’M NOT NAÏVE OR A PRUDE!!” I want to scream out in my defense, both to those who assume wrongly and to those who might suspect. But my scream has long been silenced by the fear of judgment, of criticism, of rejection. Why do I need to scream anyway?

I have “fooled around” with a couple of guys in my life. The first one, at age 19, was my university lecturer. He was probably triple my age but I let him touch me because I was in such desperate need of attention and care amongst the chaos of my life at the time. I hated his hands on my body and his lips on mine. Initially I said nothing and went along with whatever he wanted. When he tried to fuck me, I had to tell him that I’d never been this close before. He was going to figure it out pretty soon anyway, right? But, he just rolled over, his back to me and never touched me again. That was the end of that.

For the next 12 years I said nothing to no-one. No guy was even on my radar, let alone close enough for intimacy. I was confused, depressed and held myself hostage to my own walls, the ones I’d carefully built up to buffer myself against further rejection. I thought maybe I was a lesbian, cos I hated that man’s touch, yet I was not sexually attracted to women. So, I decided I must be asexual and concluded that love (and sex) just wasn’t for me. I didn’t need it. Instead, I threw myself into my nursing career and my travels and buried any questioning feelings with food.

Then, while travelling aimlessly around Africa searching for my soul, I unexpectedly fell head over heels for a bad-ass Kenyan guy with a good heart. He was not my type at all. But, how did I even know if I had a “type”? Regardless, our hearts connected and things went further. I loved how he touched me and how his lips felt on mine. Then, almost at the point of no return I dropped the V-bomb on him also. He had a similar reaction to the lecturer, though perhaps not so harsh. But, while it still hurt like hell, I became even more attracted to him, mostly because he had rejected me less. Then I had to return home to Australia, to reality.

In the three years since Kenyan-Guy and only a handful of awkward, ill-fitting dates, I haven’t had to think much about sex. But, now I think I’ve met a guy. I am attracted to his energetic spirit, his humour, his eyes. I don’t know if anything will even happen. But regardless, my virginity fears are oozing to the surface. I want a real, honest and loving relationship involving growth and connection on all levels, including intimacy and sex. But, in order for this to happen, I need to have a rather challenging conversation with the guy, whether it’s with this guy or someone else. Where do I even start? How do I explain myself? Will any guy even want me once they find out? I am so scared of being rejected again that I’m teetering on the edge of resigning myself to voluntary singledom forever. That scares me as well, because I can’t shake that deep desire for just a chance at real love. But, how do I begin to move forward and tolerate being a virgin in a non-virgin world?


Never Been Laid

Join Jen Pastiloff  and Emily Rapp at a writing and the body retreat in Stowe, Vermont Oct 2015. This will be their 3rd one together in Stowe. Click the photo to book.

Join Jen Pastiloff and Emily Rapp at a writing and the body retreat in Stowe, Vermont Oct 2015. This will be their 3rd one together in Stowe. Click the photo to book.

Dear Never Been Laid,

Let’s start with something from the old horse’s mouth shall we? “I want a real, honest and loving relationship involving growth and connection on all levels, including intimacy and sex.” Congratulations! I’m proud of you for writing this down and announcing it to me, to the readers and most importantly yourself. Now go download as many woo-woo, hippie-dippie, self-love meditations as you can (my favorite is Loving Kindness with Sharon Salzberg) and promise to go on a listening binge of at least one a day until you develop said relationship with, you guessed it, yourself.

As for this conversation you feel compelled to have with this “new guy or someone else,” let me be the first to say SOMEONE ELSE!, and by that I mean, yes you guess it again, yourself. Here’s a writing assignment. At the top of a page scratch out the following question: What exactly am I waiting for? And then be really really honest with yourself about answer. Because as one who has spread her legs for the cause, I can tell you that virginity never got me anywhere, least of all a quality relationship.

So now that we know that one’s status, as far as past proximity to a penis goes, has no bearing on whether or not one gets to fall in love, let’s explore the former, shall we? I hereby release you from the obligation to tell anyone else whether or not you’ve been intimately involved with a one or not, or by how much or when and with which one and so forth. These details belong in your private domain and do not necessarily need to be released to anyone at any specific time, least of all to a man who you might want to get it on with later. Which is not to say it can’t be shared, but rather to say it’s not a requirement.

Now this might be controversial, because doesn’t a loving relationship include baring witness to each other’s every thought, fear and potential future hurt? To this I answer with a resounding, NO. Instead, may I suggest that it is your business to decide when you want to make advances to the penis and how close and in what order. It is the owner of that penis’ business to treat your body and his with decency and care. As for this virginity thing, it is simply besides the point, not to put too fine a tip on it.

I hate to be such a feminist about this, but if we want to be historically accurate, the very idea of virginity requires us to look at a woman from the outside, to judge her as having or not having a certain objective value, as if that exists, and in that sense, has little to do with being the owner of the body of the woman herself. Now, you might say, that body cares about virginity if the first time is going to be painful. But if you ask me, losing your virginity is about as monumental as eating at a restaurant that you are not dying to return to but didn’t mind having eaten at to begin with. No more, or less. Sorry to disappoint.

No, NBL, what I’m more concerned with is your deprivation attitude about touch, whether it be from a man, a woman or a hard boiled egg. This black and whiteness about your external status has robbed you of all the glorious in betweens, of sweaty palms and panting kisses and hot rubbing between the legs. These little under-the-covers activities, my curious friend, are where you want to start.

In the meantime, remove the V word from your vocabulary all together. It’s doing you no good, and it’s separating you from the rest of your kind. Meaning, US! All the sexually active in some way shape or form woman who are no more close to an unattainable perfect virgin or an unforgivably fallen whore, than you, dear NBL. In fact, let’s just call you Newly Blossomed Love instead, for the relationship you’ve formed with yourself as a result of writing this deeply telling and emotionally cleansing letter. Again, we’re proud of you for knowing what you need. Now go out and get some!


Lots of Love,

Life (aka Emily)

Emily Scarlet Kramer is the co-author of The Hot Woman’s Handbook: The CAKE Guide to Female Sexual Pleasure.

Please note: Advice given in Dear Life is not meant to take the place of therapy or any other professional advice. The opinions or views offered by columnists are not intended to treat or diagnose; nor are they meant to replace the treatment and care that you may be receiving from a licensed physician or mental health professional. Columnists acting on behalf of Dear Life are not responsible for the outcome or results of following their advice in any given situation.

Jen Pastiloff is the founder of The Manifest-Station. Join her in Tuscany for her annual Manifestation Retreat. Click the Tuscan hills above. No yoga experience required. Only requirement: Just be a human being. Yoga + Writing + Connection. We go deep. Bring an open heart and a sense of humor- that's it! Summer or Fall 2015. It is LIFE CHANGING!

Jen Pastiloff is the founder of The Manifest-Station. Join her in Tuscany for her 2nd annual Manifestation Retreat Sep 26-Oct 3 (ONE SPOT LEFT.) Click the Tuscan hills above. No yoga experience required. Only requirement: Just be a human being. Yoga + Writing + Connection. We go deep. Bring an open heart and a sense of humor- that’s it! It is LIFE CHANGING!

Featured image courtesy of Robert Bejil Photography

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  • Reply Barbara Potter April 8, 2015 at 3:31 pm

    You rocked it Emily <3

  • Reply Late Bloomer April 8, 2015 at 4:09 pm

    I could have written this a year ago. I waited until I was 31 to become intimate with a man and that was last year. Yes, I waited so long but it wasn’t because I was waiting for marriage or anything either, it just hadn’t happened. I guess you could say nothing ever lined up for me, it never felt right, something always felt off. I am firm believer in trusting yourself and making no apologies for it.
    I didn’t date much and those I did just didn’t really do anything for me. Then there was unrequited love that leads you absolutely nowhere. So I delved into myself and just became self-sufficient & happy on my own. By most accounts people never suspected anything. Although, I always kind of felt awkward, like yeah sex, ha, when the topic came up in a group. But to be honest I wasn’t really a prude either, I mean I was curious, but I just hadn’t found the right partner.
    Then I met my now b/f. I was on a dating app when I came across his picture and that little voice was like “Yes!” I eventually messaged him first. The thing about him is that we have always just had so much fun together and everything flowed into taking the next steps in our relationship. When things did get hot & heavy one night I told him I wasn’t that experienced (he seemed surprised) and then I was just like nothing had ever really worked out before. He didn’t get all weird about it (Thank God) and he was fun, kind and silly about it. Eventually, it did happen and it was fun and great. Did it really change me all that much, not really I’m still me… I’ve just have had sex now. Be kind with yourself. You’re unique & special and someone will see that and love it. Just let yourself be guided to the right person and there is absolutely nothing wrong with taking your time.

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