How to Know You're Ready To Lose Your Virginity

We’re always hearing that we could be having better sex, a better orgasm, or a better relationship. But how often do we hear the nitty-gritty of how we can actually better understand our deepest desires and most embarrassing questions? Bustle has enlisted Vanessa Marin, a licensed sex psychotherapist based in San Francisco, to help us out with the details. No gender, sexual orientation, or question is off limits, and all questions remain anonymous. Now, onto this week’s topic: How do you know when you're ready to lose your virginity.

Q: I’m 27 and still a virgin. I’m not religious and I'm not waiting until marriage, but I haven’t found a guy that I like enough to sleep with. The longer I wait, the bigger of a problem it seems to become, and now it’s to the point where it’s causing me a lot of anxiety. I’m getting so frustrated that I feel like I should get it over with and sleep with someone random. I got close to having sex once, but I made the mistake of telling the guy that I was a virgin. He freaked out and said he didn’t want the pressure of being my first. Now I’m embarrassed to tell guys that I’m a virgin, so I feel like I should keep it a secret. What should I do?

A: I've received a number of emails from later-in-life virgins over the last few weeks, and they all sound roughly like your question. They have been from people like yourself, who didn’t intend to make a big fuss out of losing their virginity, but never ended up finding someone they actually wanted to sleep with. Each email has expressed your exact conundrum — should they get it over with or keep waiting?

It’s worth pointing out that most people who are virgins past the age of 18 tend to feel like they’re one of the last people in the world to have sex. Unfortunately, all of us struggle with not feeling “normal” in one way or another when it comes to sex. I can practically guarantee you that if you had lost your virginity earlier in life, you’d be worried about being sexually “abnormal” in a different way. Here's what you should keep in mind.

No Big Deal?

The frustrating thing about virginity is that even if we try to not make it a big deal, it still seems like one. You will think of your first time more than other times, simply because it’s the first. We tend to remember our firsts — first kiss, first fight with a boyfriend, first time moving away from home.

It sounds like your original requirements for losing your virginity weren’t that strict. You just wanted someone you liked, not someone who felt like your soulmate or someone you could see yourself eventually marrying. That’s a perfectly respectable goal to have — after all, why would you want to sleep with someone you didn’t particularly like?

The problem seems to be that as time goes on, you’re finding it tricky to stick to your original values. The judgment you feel around being a virgin at 27 is starting to outweigh the importance of liking the person with whom you have sex.

The Two Questions To Ask Yourself

(No, that's definitely not one of them.) My advice to you comes down to asking yourself two related questions: “How do I want to feel afterward?” and “What do I want my virginity to mean?”

Take some time to consider how you’d like to feel right after losing your virginity. Excited? Relieved? Loved? Satisfied? You can also think about the feelings you’d like to avoid, like regret or shame. The frustration you have been feeling is pushing you to "get it over with," but what would it feel like afterward to actually have done so?

This is also a good question by which to judge each potential partner or situation. Say you’re out on a date with a guy and considering losing your virginity to him. Do you think you’re more likely to feel content or distressed after sleeping with him?

Taking the time to consider how you’d like to feel in the afterglow of your first time will help you answer the question, “What do I want my virginity to mean?”

And Don't Forget...

The bottom line is this: Your virginity gets to mean whatever you want it to mean. You’ve probably gotten bombarded by all different kinds of messages about virginity, but it’s up to you to make a conscious choice about what you want for yourself. You get to choose if you want to wait until marriage or if you want to treat it like any other sexual experience.

You decided years ago that you wanted your virginity to mean enough to wait for someone you liked. Even with all the frustration and embarrassment, is that still your value? If yes, then I think you have your answer: Keep waiting until you find someone worthwhile. I know you feel like you’ve been waiting a long time already, but reaffirming your values should help make that decision feel a little more comfortable.

If you take some time to consider these questions, you might realize that what’s important to you may have changed now that you’re a little older. “Getting it over with” might feel like a decision you could conscientiously make. If that’s the case, having taken the time to be truly thoughtful about your values will make you feel a lot better.

but should you tell your partner?

These two questions can also help you decide whether or not to tell a partner that you’re a virgin. How would you imagine feeling afterward if you had lied about it? Is honesty an important value for you?

In general, I tend to favor telling the truth about your virginity. Any potential sexual partner is going to have his own set of values around virginity, and I think he or she deserves to be able to make an informed choice. The guy who turned you down did so in an unkind way, but I’m guessing that the meaning he places on virginity guided his decision. He just wasn’t the right guy to take yours.

If you decide to tell a partner, do it before you start ripping each other’s clothes off. This will help minimize potential embarrassment. Say something very simple and straightforward like, "I want you to know that I haven't had sex before, but I do want to have sex with you. I'm a little nervous sharing this with you, but I wanted to be honest. I hope you can respect that."

Finally, I want to offer one last piece of advice: Don’t be ashamed of your virginity. There's absolutely nothing wrong with not having had sex yet. Being a virgin does not define you. It is just one very small part of who you are as a person.

And most of all, if someone ever tries to insult you about it, just take a cue from Cher Horowitz herself and call them on it.