Confessions of a 27-year-old smart virgin.


The memory of telling G* I was still a virgin at 25 sits clearly in my mind. We’d gone on four dates and fooled around on our third date. I’d enjoyed it, but wasn’t ready to have sex. It was important for me to be clear on my comfort zone: I was happy to fool around, just not ready for full intercourse. I didn’t want to hide why.

So I sat on my couch, palms sweaty. The words came out stumbling, uncertain. Looking back, they seem both vague and accurate. I had a history of intimacy issues. Trusting people was hard for me. So I just…hadn’t had sex yet. I wasn’t waiting for marriage, I just wasn’t ready to do that. I needed something more committed to have sex. I could do other things, just…not that.

I distinctly remember looking at my tired rug, not at him.

What did he say? It sounded right at the time. He accepted it, acknowledging my reason as valid. It was such a relief. Here was the answer I’d needed.

"I distinctly remember looking at my tired rug, not at him." Image via The OC, Fox. 

A month later with multiple dates, I asked that we either get serious or split. G called my virginity a ‘sexual roadblock’. His sudden shift left me with emotional rug burns.

Previously, we had seemed fine. Our dates had been a mix of fun conversation and usually ended up in my bedroom. I was too shocked to ask him why he hadn’t said anything earlier. I was too ashamed to ask any questions about my bedroom performance.


I never got those answers: that was the last time I saw him.

Dating and vulnerability, for me, have always gone hand in hand. For a while, I avoided both. I was scared of rejection, terrified that I’d be mocked because I’d barely kissed anyone. My fear filled my imagination with rejection. I wasn’t thin enough. I wasn’t pretty enough. My intelligence was too intimidating. I was too bossy.
Who could date a girl like that?

So I didn’t date, not in high school, not in college. There were one-off make out sessions. They felt good, but left me emotionally unsatisfied. As time went on, age became an issue that loomed in my mind. Who could want to date a feminist virgin at this age? My own inexperience made me feel like a freak.

Women in the Mamamia office reveal how they lost their virginity. Post continues below. 

A few things made me begin to see things differently. First was Brene Brown’s book, ‘The Gifts of Imperfection’. It blew my mind: I wasn’t alone struggling with shame, we all do. I didn’t have to be perfect to be loved and accepted. In fact, sharing my vulnerabilities would help me connect.

My own inexperience made me feel like a freak.

Another critical aspect was therapy. I still remember bringing up dating at one point. My therapist pointed out that we couldn’t work through my issues if I didn’t date. I didn’t have to be successful, I just had to try.

So, at the ripe old age of 23, I began to try.

Vulnerability in dating, I learned, was a multi-layered beast (sadly, more like an onion than a parfait). I found ways to test the water, giving myself the opportunity to see if I wanted to go further with someone, both emotionally and physically. I’d ask questions about important but less sensitive issues. I tried to be upfront sharing my belief in intersectional feminism or faith in God.

"So, at the ripe old age of 23, I began to try." Image via 'That Awkward Moment', Focus Features. 

Sometimes, discussion of hypotheticals told me more than enough. If someone disparaged therapists, they weren’t going to have a second date with me. Why should I date, let alone sleep with, someone who’d mock the very kind of doctor that helped me deal with depression?

Both of these techniques helped me to realize that vulnerability wasn’t an all or nothing. I could find safe ways of choosing what to share, who to be open with, and how to share it.

Creating these tests reminded me that dating wasn’t just about me being chosen, but choosing men as well. Obvious, I know, but this helped me gain confidence. It also made me ask myself an important question: what did I want in a relationship?

Trial and error showed me: a man who was willing to be vulnerable and honest. Someone who wouldn’t just say he wanted a relationship and run when work got busy (like B did). I wanted someone to be as real with me as I was with him, whether about sex or his family. It wasn’t just about emotional connection but also feeling good physically. I wanted to know what turned him on. More importantly, I wanted him to ask that of me too.

And yet, so many were barely able to tell me about their sexual history, let alone ask for what I wanted. When I asked one man to get tested before we did unprotected oral, he objected. He didn’t need to get tested because ‘he wasn’t a Casanova’. Luckily I tested clean after our last encounter.

"What did I want in a relationship?" Image via iStock. 

Dating has had scary moments. D, a former chef, couldn’t understand why I objected to a high end restaurant on our second date. When I tried to stop seeing him, he even tried to persuade me that I owed him a second chance. His pressure, after just one date, terrified me. If he was this insistent now, how did anyone break up with him?

Thankfully, I could just block his number.

Whether rejection or pushiness, dating failures revealed my own resilience. I could get over being ghosted. I could tell a man no. Hurt feelings? Nothing a cigarette or tequila couldn’t fix.

Though I dated a variety of men, very few learned about my virginity. After G, it was hard to believe that I’d be safe saying it. How could I know that they weren’t just saying okay to sleep with me?

This fear wasn’t the only scar. Many were drawn in initially but left after we fooled around. It felt like I was pretty enough but hadn’t performed well enough, like my pale skin and big boobs had promised something that I couldn’t deliver. I had a sexual image, but couldn’t deliver on it.

Was my read on these events based on reality? Too many men have just ghosted, giving no answer, only coward avoidance. True, G threw my virginity in my face. Then again, He only disclosed he was coming off a bad breakup when I asked to get serious, two months into dating me.

Still, the silence and hurtful words made my own terrible myth that much easier to believe: They could fuck me, not love me.

Less than a month ago, I turned 27. I’m still single, still a virgin. Busy with work, travel, and my friends, I haven’t focused on dating for the past few months. As much as vulnerability gets easier, dating exhausts me. Sometimes, I just don’t have the energy to put myself out there.

"I'm still single, still a virgin." Image via iStock. 

Yet, just like every other birthday for the past few years, I think about my virginity. I’m another year older and I’m becoming more, not less, of an anomaly. Sometimes doubt creeps in and asks: Am I doing relationships and life wrong?

Yet, four years of navigating dating and vulnerability helped me clarify what I want. I’m not looking for something casual. There may be plenty of people who’ve had sex, but far fewer willing to share their authentic selves. Far fewer are willing to be vulnerable and open about who they really are, what they really want.

I guess I’m an outlier, holding out for someone who can give me that intimacy, physically and emotionally. I don’t mind: I deserve nothing less.

*All names have been changed.

Katie Simpson is a writer and photographer, you can see more of her work at here or follow her on Twitter and Facebook. This post originally appeared on Medium and was re-published here with the author's permission.


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