Dear Wendy: “Should I Reclaim My Virginity?”

Until recently, I was a 24 year-old virgin. In high school I thought I wanted to wait until marriage to have sex, but over time I decided to simply wait for the right guy to come along who I trusted. Several months ago I started dating Chris, whom I’d had a crush on for awhile. I fell hard for Chris and decided he was the guy I wanted to introduce me to sex. Unfortunately, by the time I did sleep with him (after three months), our relationship had already started to deteriorate, and as a result, our sex life started out in a bad context. We only had sex maybe a dozen times before we broke up and he really broke my heart by doing so. Now I feel conflicted about sex. I’ve always been a very sexual person (abstinence was difficult for me, and I’d been doing things like oral sex in my previous relationships), and I enjoyed having a sexual relationship with a man. But I feel like with Chris I never got to experience sex in a loving context with a guy who cared about me, and I’m starting to regret losing my virginity to him. Maybe I should reclaim my “second chance” virginity and wait until I’m engaged or married to have sex again so that I don’t go through the heartbreak of being intimate with a guy who’s just going to morph into a douchebag. Or, do you think the problem is just that I slept with the wrong guy too soon, and that I should keep trying to have a satisfying sex life with boyfriends in the future? — Leery

OK, first of all, let’s get on the same page with our lingo. There’s no such thing as “second chance” virginity. You experienced what you experienced and no made-up phrase is going to erase it for you. Furthermore, it’s our experiences that make us who we are, that help distinguish us from other people and from our own past, and that contribute to our personal growth. You may see this particular experience as a “mistake,” but that doesn’t mean you can’t learn and grow from it. In fact, it’s our mistakes that often teach us the most.

The real mistake here isn’t that you had sex with someone you now regret sleeping with; it’s thinking that there’s some magical way you can avoid heartbreak in the future. There’s not. Abstaining from sex will not save you from making mistakes in love or life. If you believe it will and that’s why you think you should remain celibate until marriage, you’re going to be disappointed. Life — and love — is full of hurt, and sex most certainly isn’t the only path to feeling it.

Sure, there are ways you can reduce your risk of being hurt, but you do so at the risk of missing out on life experiences — of not living as fully as you could — and even then there’s no guarantee you’ll avoid a broken heart. You can decide not to have sex until marriage; you can close your heart to potential suitors; you can stop having relationships altogether. But where does that leave you? Certainly not in a more joyful place — not if what you’re hungry for is the very thing you’re giving up and not if you’re giving it up for the sole purpose of avoiding pain.

Be smarter about your decisions in the future, but don’t eliminate them completely. Be more cautious about the people you open your heart to in the future, but don’t close it off altogether. You can’t avoid getting hurt, but you can reduce the value you put on your pain. You can accept that pain is a part of life, that it happens to all of us, and that it’s a momentary set-back that won’t keep you from finding happiness, love and fulfillment. Not if you don’t let it, that is.

*Do you have a relationship/dating question I can help with? Send me your letters at dearwendy@thefrisky.com.

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