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Auntie SparkNotes: Should I Tell Him I Wasn’t a Virgin?

Hi Auntie,

I’m 18 and have been dating my boyfriend for four months now. I love him so much and I trust him too. However I lied to him about my virginity when we met. I had sex at only 14, a lot of times, until I decided to quit and wait for marriage after a very painful heartbreak. I decided to keep secondary virginity.

However, when I met him, I felt I should have sex with him coz I really trusted him. I wanted to share intimacy with him. It was a hard decision to make and we’ve had a lot of sex since then.

Our relationship wasn’t based in love until a month ago when we felt we really loved each other. And now that I love him, I feel very guilty and ashamed for lying to him. I also slept with someone else twice back when we were first dating. (I did it because at that time my boyfriend didn’t want to commit to me and I was bitter.)

I don’t feel insecure that he might dump me after knowing the truth because he’s mature and I trust his love. But I’m confused whether he should know all this. I love him too much to watch him hurt. I really don’t want to wound him and his ego (he feels really good thinking he broke my virginity.) Please help, I’m so confused and I want to clear my guilty conscience.

And we’ll definitely talk about that, Sparkler. Absolutely. For sure.

That is, right after Auntie SparkNotes gets over the brain-melting dissonance of a guy who prides himself on deflowering virgins being described as “mature.” That is… not the word I would have chosen.

But then again, that’s not the word I’d choose to describe any of this, from your impulsive sexual behavior to the various lies you’ve told about it. I’m telling you this not to hurt your feelings, sweet pea, but because it’s important: This tangled web of delusion and dishonesty didn’t just happen. You made it, all by yourself, one sticky thread at a time—beginning with the lie you told yourself about keeping “secondary virginity.”

Which, as you’ve discovered, is not actually a thing. It’s not that you can’t revisit the choice to become sexually active, and choose differently moving forward; it’s just that the second choice doesn’t write the first one out of existence. You can’t undo your past. And trying to pretend otherwise is probably the least healthy, useful, or productive way on earth of dealing with regret, because it doesn’t change what happened. It just hides your experience behind a wall of denial, where you can’t learn anything from it… and where it makes you ironically that much more likely to do the same thing all over again.

As you’ve, um, also discovered.

What that means in terms of your current conundrum is just this: Deciding whether or not to come clean with your boyfriend needs to wait until after you’ve figured out how to come clean with yourself. Specifically, you need to look back at your letter, and ask yourself why, when you list all the various reasons why you’ve chosen to have sex at one time or another, “because I wanted to” is conspicuously absent—when that should be the first, best, biggest reason of all. When did you decide that what you wanted was so unimportant? And is there perhaps a connection between the devaluing of your own desires and, say, your impulsive choice to sleep with someone else because you were angry at your boyfriend—or, for that matter, your choice to date the kind of guy who was willing to sleep with you but not commit to you, who sees your virginity as a prize? What might your life look like if you had made your happiness, your feelings, a priority, instead of allowing yourself to be batted around by a million external influences? What if you made it a priority now? What if you had the courage to be your own guide again?

To be clear, I don’t know the answers to these questions. All I know is what’s in your letter. But there’s more than enough there, in those three paragraphs, to read between the lines and see someone who doesn’t believe she matters much. Nobody is this careless with their own heart, or their own body, unless they’ve already convinced themselves that they’re damaged goods. And for you, the way forward isn’t to seek absolution for that carelessness from one of the various people you’ve been pushing aside your own agency for. It’s to retake control with both hands—all the power, all the responsibility, all the paths available for the pursuit of your own happiness. It’s to allow yourself to be a person with a past, and to be open, honest, and proud of what it’s taught you, even if you stumbled along the way.

It’s to make yourself the one who can not only forgive your regretted choices, but own them, learn from them, and move on to make better ones with the benefit of hard-won experience.

As to what “moving on” means in this case, I will venture a guess that only one of your secrets needs to see the light, although not the one you might expect, and not for the reasons you might think. Your boyfriend isn’t entitled to know that you weren’t a virgin when you guys got together, no matter how big of an ego boost he got out of the idea that he’d deflowered you. But you, darling, are entitled to a relationship in which you’re able to share formative truths about who you are and where you’ve been, and that includes the part where you once got your heart broken so badly that you felt like you had to rewrite your own history to try to escape the pain. That’s the kind of thing you should be able to tell somebody who you love, who loves you.

It’s also the kind of thing a person worth your time will understand and not blame you for.

But that part is step two. Step one is empowering yourself to consider all of this in an emotionally healthy way. The framework of agency and responsibility comes first, before you start making any decisions about which truths to confess, and to whom. Because with that framework in place, you can be confident that your choices are in service of your values and your happiness. And whatever you end up choosing, you’ll know that you did it for the right reasons.

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