Illustration by Maxine Crump.

I recently tried to have intercourse for the first time after very serious and lengthy deliberation and to put it lightly, it didn’t go well. In fact, it technically didn’t happen at all because, well, you could say the P didn’t exactly get in the V. After millennia of people and animals doing this thing, I was kind of stunned that I couldn’t even execute it, let alone execute it well. I’ve read stories about people who’ve had bad first times, where they might not have been into the person or there might have been some brief fumbling, but I’ve never come across someone who couldn’t actually figure out the mechanics of sex itself. It was bizarre—we’d researched the subject, prepped a ton, and then…it literally didn’t come together. What do I do?! I feel so confused and frustrated. It makes me wonder if I’ll ever be capable of having sex at all. —Tori, 20, Alberta, Canada

Hello Tori! First off, I promise you-if you want to have sex, you are capable of having sex. It sounds like you’ve thought everything through, really educated yourself, had some open and honest discussions with your partner- all of that is great stuff. And I know you’re right, this is a thing people have been doing for millennia, but for a millennia, people have also been having issues with putting the P in the V that they think are theirs alone.

My first suggestion would be to see a doctor, if you haven’t already. There are some biological issues that can result in penetration being quite difficult—endometriosis, hymen issues, overly strong pelvic muscles- and it’s just best to get yourself checked out to eliminate possibilities or start working on a medical issue. But assuming there’s no immediate physical cause, let’s focus on what else could be happening. My uneducated guess is that this issue might be more anxiety-related than a physical thing. Based on your question, I can see that you are very thorough person, and I’m right there with you. I will endlessly research hotel/beauty treatment/car options, always looking to fill in the picture in my head of how things are going to go, always looking to be prepared. It’s part of who I am, but I have found over the years that sometimes too much research turns the thing I’m researching, whether it’s a fun experience or a new laptop, into a monstrous psychological mountain rather than whatever size molehill it is in reality. I’m so crammed with facts and options and hot Internet takes that I am almost paralyzed into inaction because I’m trying so hard to approximate leaping with my looking. In a bid to be prepared, I paint myself into an anxiety corner, and what I do know is that it’s very hard to have good sex when you are anxious. So I would invite you to not research anything else about sex anymore and to instead, try some deep breathing, yoga, meditation, watching cartoons, whatever relaxes you, and remind yourself: people have been doing this for millennia, and people have definitely experienced what you’re experiencing. It’s okay if it happens and it’s okay if it doesn’t. It’s okay if it’s weird or awkward or sexy or strange, so long as you feel safe. Overthinking could be what’s happening between you and your partner no matter how you feel about each other or how much research you’ve done.

So in a bid to relax things a bit, it’s time to start experimenting, and for that I would recommend exploring yourself with a penetrative sex toy. Not as a replacement for your partner, but as a way of getting comfortable with the unique sensation of being penetrated in an environment that is entirely your own. Buy yourself a penetrative toy (they are on Amazon these days if you don’t want to shop in person), block off some private time, and start seeing where things feel possible, and where things feel impossible. What feels good? What feels strange but interesting? What feels bad? What is fantastic about doing this is that you are completely in charge of the experience, and no harm or embarrassment or weirdness can happen, so you can do try whatever you like and see how things feel. A wise older woman once told me that you should know how to give yourself an orgasm before you allow anyone else to attempt it, but I think the same can be said for getting to know your genitalia before you introduce anyone else to it.

Finally, realize that sex isn’t just P in V. Sex is so many things. Outercourse! Oral! Digital play! Mutual masturbation! Phone sex! If you and your partner haven’t yet, start exploring any of these other avenues that you feel comfortable with and have fun. Yes, FUN! This is supposed to be a fun, friction-filled exploration of your emotions and your bodies and what turns you on. You can use it as a ramp up into P in V (have you noticed that I like your description?), or you can use it as its own sexual experience, because any of the things I mentioned absolutely can be hella satisfactory on their own.

I am confident that someone as smart and thorough as you, Tori, will figure out what’s going on with you. Sex is one of the few times in life where we are encouraged to get out of our heads and just feel. Keep experimenting and you’ll figure it out. ♦

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