Advice and Insights for Modern Daters

Navigating Singledom as a Virgin


“I’ve seen The Bachelor a few times in passing with my ex. They’re all liars on there. I remember this one girl was claiming to be a virgin. That’s bullshit.”

That is an actual quote from my latest date. He also pretended to try to get the check after finding out I was 29-years-old, rather than the 24 years he thought. Yeah, he wasn’t a winner. And neither was this guy I went on a date with a couple of years ago. We had mutual friends, some of which wanted to set him up with a fellow twenty-something virgin. He told me, “Because I’m religious, people try to set me up with virgins. But that is not what I want.”

This was before the Bachelor days when the whole world didn’t know about my lack of bedroom experience. I went to the bathroom, disturbed enough during that date to call my mom and tell her how disgusted I was by his comment. I had never said anything about being a virgin to him, but he definitely found out!

Those are just a few demonstrations of how much more complicated dating is these days as a virgin. After coming off of my first season of The Bachelor, I wrote an article about how frustrating it was that people couldn’t grasp the fact that I could be a virgin and still not present myself like an Amish person. Now, I’m frustrated by something that affects my life much more than that. It seems as though my virginity is such a turn-off for guys.

I was 25 when it first became an issue. I was in life altering lust with one of the most studly men you’ll ever see. He liked me, and I knew he was attracted to me, but after a few PG-13 make outs, I sensed him getting distant. He ended up telling me that he wasn’t in the place for a relationship (which I knew was 100% the truth going into it, not just an easy way to get out of things) and I wasn’t a hookup girl. He didn’t want to be my first if he knew he couldn’t commit to me at the time. When I told people this, they respected him for it, and deep down I did, too. It was thoughtful and proved to me he cared about my feelings. But just typing this, my eyes are welling up because hearing him say that was the most disappointing, frustrating, and hardest thing I’ve ever heard. I felt like I was being punished for my inexperience. This was the first guy I’d ever desired to go past second base with. He was the first guy I knew I wouldn’t regret sex with.

This would be the time to tell you that my decision to remain chaste isn’t religious. It’s personal. I don’t crush easily. I can pretty much count my major crushes on one hand. I didn’t feel the right balance of comfort, safety, and all consuming attraction to someone until this guy. That was the feeling I was waiting for. I knew I would feel “grossed out” or regretful if I had sex with someone who I didn’t feel that way with. How could it be that I’d waited that long for that feeling and then the guy I felt that way toward wouldn’t see me anymore because I waited for it? I was heartbroken. If you thought I cried a lot on Bachelor in Paradise…ha! I hated my virginity. I looked at it as such a burden. It stood in the way of being with the guy I wanted to be with.

…my decision to remain chaste isn’t religious.

Fast-forward eight months and I started seeing him again. I don’t know how I schemed that, but I did. Things got a little “dirtier,” if you know what I mean, and even though we got close, we didn’t have sex because honestly, I was afraid we would and then I wouldn’t see him for weeks after, or he wouldn’t text me the next day. I realized that maybe commitment was something I wanted to have after waiting this long to give it up.

Three years later, I would love to say I feel the same, but I’m not sure I do. I’ve dated multiple guys in the past couple of years who probably would have invested more time or would have seen me in a more sexual light, had I not been a virgin. Most guys I sense feel like they can’t just date me casually. I’m not saying I don’t want to be taken seriously, but they really feel like they need to make a decision about dating me quickly. They don’t want to deal with the possible emotional repercussions.

You know how they say girls can get clingy with their first…especially if they wait out as long as I have? That’s a factor. Plus, what fun is dating a girl you “can’t” have sex with? Oh boys, I’d make it very fun. I feel like I never get enough time to prove how cool of a chick I am. Or even if I do, in the back of their head they’re thinking, “I’ve got to marry this girl or bounce,” even though I don’t plan on waiting for marriage. Luckily, most of the guys I go on dates with don’t watch The Bachelor, but there’s always Google, so the V-card thing isn’t something I can hide for long (nor should it be).

I know what you’re going to say: you don’t want to be with guys who think of your virginity as a turn-off. If a guy isn’t into you as you are now, you don’t want to be with him…he’s not the one for you. The one, “they” say, will love that he’s your first. Yes, yes, probably. Maybe my virginity is a nice way to weed out the guys who aren’t right for me. But as I encroach 30, part of me craves to just date like a “normal person.”

Ironically, the guy mentioned above is the only guy I’ve had strong feelings for who tells me I’m sexy and who messes around with me like I’m not a porcelain doll. My virginity doesn’t scare him. He honors it, I think. I haven’t seen him for a while, but I feel like I hold on to him in my mind for a couple reasons, and this is probably a major one.

Not to sound like Carrie Bradshaw, but I can’t help but wonder why so many of my gorgeous guy friends (#BachelorFamilyProblems) have a blast with me, but choose to date (or at least hookup with) girls who kind of have less personality than me, or aren’t conversational as me, but are perceived to be sexier. It makes me feel like shit. It makes me feel undesirable. Do you have to have sex to be desirable? Maybe I should have just lived back in the olden times when virgins were the ones that were put on a pedestal.

Of course, using a dating app does present its own set of challenges. When I meet people through friends, they’ve usually heard I’m a virgin. I’m not sure what the protocol is with guys from Hinge. Do I tell them right away? Let them figure it out as we get to know each other? I’m really not sure. Sometimes I worry things will turn out like they have with so many of guy friends. We’ll have a blast together, but they’ll choose to date girls who, in my opinion, have less personality and are willing to hop in the sack right off the bat. It’s almost as if being less conversational is seen as sexier.

What’s a girl to do? Seriously. Help. Give me advice. Should I have sex with a guy I love and trust, but I’m not in a committed relationship with, get it over with, and date “normally” for a millenial? Or should I be patient and become the next Steve Carell in The 40 Year-Old Virgin and wait for the right one? I guess the latter sounds oddly more romantic. I am a hopeless (too hopeless, I suppose) romantic.

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