Dear Em & Lo: How Do I Tell a Guy How Inexperienced I Am?

photo by Balakov

Hey Em & Lo,

I’m currently 26 and, yep, a virgin. I haven’t been “saving myself” and have no reason for this phenomenon other than I’ve never had the opportunity! (I had low self-esteem in high school, I was involved with theatre in college and all my crushes were gay in college, blah blah blah.)

I’ve never been in a relationship, and since I don’t want to lose the v-card to a random guy or someone I don’t trust, I haven’t done the deed yet. Here’s the tough part: I also haven’t done anything with a man past making out and a little first base. Again, this has not been by choice, the opportunity just never presented itself! Luckily, I may start dating a guy really soon, and I’m excited to see where it goes….

Here’s my problem: while I’m perfectly comfortable telling him that I’m a virgin and that I’ll gladly and willingly have sex with him sooner than later, how/do I tell him that I’m way more inexperienced than most women my age? I have no history with giving a blowjob, receiving oral, or even giving a handy!! (Ugh, sad, I know). I’m so afraid that 1. It’ll turn him away and I’ll never gain that experience or 2. That he’ll be okay with it but I’ll be TERRIBLE at all of it. It’ll be like being with an inexperienced teenager!

Do I come clean when the situation arises? Do I practice at home? Or am I doomed to live forever as a sad, sexless spinster? Help!

— The 26-Year-Old Virgin

Dear 26-Y.O.V.,

First of all, can we just say how happy we are to hear that your low self-esteem in high school translated to zero sex? For many girls, low self-esteem at that age translates to lots of unsatisfying, even dangerous sex or years of unreciprocated oral sex with assholes. Consider yourself incredibly lucky that instead, all of your low self-esteem lead to the theatre and some unreciprocated crushes on gay men. You clearly weren’t ready to have sex back then, and because you managed to avoid it (or because sex managed to avoid you!), it’ll be all the more fun now that you are ready.

And the reason we say you’re ready is not because you’re twenty-six, but because you get that, while the guy doesn’t need to be “The One,” he does need to be someone you trust — more than just some random guy looking to collect V-cards. And if he’s someone you trust, then you can tell him everything: That you’re a virgin, not just in the technical sense, but in the truest sense of all.

If he likes you, we’re pretty sure he’ll find this confession endearing, possibly even a turn-on. You can make it clear to him — to avoid freaking him out — that you haven’t been saving yourself for “The One,” you just never got around to getting lucky. You could even joke about it, and ask him if he’s willing to be your guinea pig and let you practice on him — who could say no to that?

In terms of being prepared, you could do worse than read (ahem) one of our books, like Sex: How to Do Everything. (The links below may also help.) Some advance reading will help familiarize yourself with all of your own and his anatomy, as well as the sort of activity you might encounter in the bedroom. But don’t feel like you have to memorize the whole thing: Browse the book on your own first, and then return to it throughout the relationship — the more you do with your boyfriend, the more the book will make sense. Hey, you could even suggest reading it with your boyfriend. When we wrote Sex: How to Do Everything, our goal was for it to be the kind of book that a couple could read together in bed, i.e. it reads more like foreplay than an instruction manual. Ask your boyfriend — when you make him your boyfriend! — with your best cheeky grin, to help you with your “homework” (Britney Catholic schoolgirl outfit optional).

And here’s the thing: If you like the guy and you want to please him and you want him to please you, then you’re not going to be terrible in bed. We promise you! Good sex is simply a matter of communication: Ask him what he likes, tell him what you like — you don’t need to know in advance, just tell him what feels good when he does it — and learn as you go. Every body is different, every penis is different, every clitoris is different, so we’re all learning on the job anyway, whether we’ve had sex a hundred times or just once. In fact, you might even be better in bed due to your inexperience, because you won’t be hampered by any false assumptions about what works for guys.

Remember, above all, to be honest, be safe, and have fun! And if you’re ever not having fun or not feeling safe, then it’s okay to slow down or even stop, no matter how much you promised your boyfriend you were up for.


Em & Lo



  1. I am 22 yrs old I just turned in my v-card and I told my guy that this was my frist time and he goes really? then I’ll be gentile. Frist time was not the most mind blowing it was a little painful but I like it and most deffently will give it another go with him

  2. I second that E&L’s advice is spot on! I was a 25 year old virgin who wasn’t waiting for “The One”, rather I was waiting until I felt 100% ready. Fortunately, my first time was with a good friend who made me feel comfortable and he was more than happy to take things slow. I did what E&L suggested, which was to straight up tell him I’d never seen a naked man before, let alone give a handy, but was curious what sexy times would be like. He, of course, found it endearing and seemed happy to be my first. We had sex for a few weeks until I moved away for a new job in a new city and we parted on very amicable terms.

    Shortly after moving, I met my now-boyfriend. Even after FINALLY having sex, I still felt wildly inexperienced. I told my boyfriend that I wasn’t nearly as experienced as he was and I wanted to take things slow. Once again, he was more than happy to let me set the pace. We’ve been boning left and right ever since.

    So, I’m 2 for 2 with playing the “I don’t know what I’m doing but am excited to learn!” card.

  3. From a guy’s perspective, I think that you will be just fine. Since I learn best by reading about something and then doing, reading a good intro book sounds like a fine idea.

    Any potential partner who respects you should be fine with your inexperience. Good communication as mentioned above is critical, as is a sense of humor and being “yourself” as much as possible. Enjoy the experience – be safe (condoms and a trustworthy/kind partner) and have fun!

  4. I can totally get where you’re coming from. I was in a similar situation. I didn’t turn in my V-Card until I was nearly 32 for much of the same reasons as you. I was always up front with any guy I dated and it was never an issue… it’s one of those “say it and don’t dwell” types of things. It wasn’t that I was waiting for marriage by any means but I sure as hell wasn’t going to give that to someone I didn’t trust. I found this worked out greatly in my favor. All the time I was searching and waiting gave me plenty of time to figure out what I liked and what worked for me. I found it very easy to communicate this to my partner when the time came, much to my surprise. Never pipe down, let it be known what works for you… if he’s worth his salt he’ll greatly enjoy this. Just relax and have a good time. 🙂

  5. Em and Lo’s advice is spot on. Communication is essential to good sex – regardless of your experience level. No many previous partners/experiences a person has had, the only way they are going to know what works for THIS partner is to talk about it. Don’t be embarrassed about being a virgin still. As long as you don’t treat the issue like it’s something to be embarrassed about, it’s doubtful this guy will react negatively to it (unless he’s a douche, in which case, good riddance). Good luck to you!

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