Dear Dr. NerdLove,

I’m a 28-year-old straight white male. I am a virgin who’s had some minor success with online dating in the past though I still haven’t gotten a full-on relationship. I’m kind of socially isolated: I have plenty of acquaintances but no close friends that I hang out with.

Anyway, after having taken a three-year break from OLD after a few hard rejections online in order to take care of my mental health, I created an OKCupid account three months ago. Initially, I wasn’t taking it that seriously, I just wanted to see who was out there as well as whether or not I could get any likes with new pictures (I’ve had life long body image problems, I was worried that no one would like me since I’ve gained a little weight). To my surprise, I got several likes from girls on the platform. Most of these turned out to be duds: they were either too conservative (anti-trans, for example), not attractive to me, didn’t seem to have anything in common with me, or were bot accounts. However, there was one girl on there, let’s call her C, who seemed like a good match: she was liberal, chubby but cute, and shared my interest in video games and tabletop roleplaying. She mentioned that she wanted to get married and have a child within the next five years. This was alright with me, I wanted a relationship with a girl that could ultimately be my wife if things worked out, I eventually want children, and five years from now seems like a fine time-frame for all of this to possibly happen (I still live with my parents, but I recently finished my Masters and hope to get a job that allows me to live independently soon).

So, after a few weeks of hesitation, I liked and messaged C and we seemed to hit it off. After a few messages, she asked me what I was looking for on the site. I told her that I wanted to find love, eventually, get married, and have children. She seemed happy about that and we continued messaging for a couple of days. I was asking basic get to know you questions about her interests, her spirituality (pagan), and her life. When I ask her about her childhood, she gives a message detailing her life story: her father was a deadbeat who abandoned her and her mother when she was young, she dealt with bullying and depression all throughout middle and high school because of her weight, and she and her mother had to live with their meth-head uncle for several years after her mother lost her job. Now, this set off some alarm bells for me. I’ve had a relatively blessed, middle-class life and, besides some bullying in middle school and generalized anxiety disorder in college, it’s been pretty happy. I started to wonder if we could relate to each other, having had such different lives. I’ve also had bad experiences with girls with difficult pasts, which I’ll talk more about later on. Ultimately I decided to ignore these warning bells and keep messaging her, I couldn’t know how we’d work out in the long run, so there was no reason to give up yet.

We kept messaging, but eventually, her replies started to become shorter and less detailed. I thought maybe it was because she was growing tired of using OkCupid’s messenger and was unsure if I wanted to progress things beyond just talking on a dating site. I decide to message her my cellphone number in case she wants to text, but she says she’d feel more comfortable using snapchat, so we do. We continue messaging and out of nowhere, she asks me if I have any major health problems. I say no and ask why she asked. She replied that she just wanted to know for future children. When I joke about her thinking too far ahead, she says she was just wondering and that she wants to have a child “sooner rather than later”.

Then, she asks me the big question: exactly how sexually experienced was I? I know some girls don’t want to date virgins, and I was hoping to get into this topic later after we’d been on a few dates. However, I decided to be honest and told her I was a virgin. She said she was fine with it and that it was pretty obvious since I was reluctant to flirt, and told me that she feared my conservative parents were to blame for my lack of sexual experience. She was worried that I wasn’t interested or sex or would object to her more taboo sexual interests, so she asked me what the dirtiest sex act I’ve ever wanted to do was.

Now, here was where I made a mistake. On one hand, it was pretty obvious to me at this point that, based on this question and other things she had said while we were messaging, that she wanted to be sexual with me sooner than I’m comfortable. I want to get to know someone and be comfortable with them before I have sex, when I’ve gotten sexual in the past with girls I had just met I left the experience feeling deeply uncomfortable and guilty. I feel I need at least three dates before I’m ready to do sexual acts with a woman. On the other hand, as a virgin with a high sex drive, I’m getting pretty impatient about losing my virginity and sometimes when I feel like a girl might be willing to have sex with me I throw out my doubts, previous experiences, and rationality and immediately try to pursue sex. Unfortunately, my rising sense of discomfort that things were going way too fast, my lust won out and I decided to answer her question.

After telling her all my sexual fantasies, I asked her what hers was. She mentioned that one of her sexual fantasies was “breeding” (being full of cum, as she put it) and this again set off some alarm bells since she mentioned wanting a child so much. I told her I was fine with her fantasy so long as she used birth control when we were having sex until we married and were ready to have a child. She replied that she didn’t use birth control, and finally I realized what was happening: she didn’t want to get married and have a child in a few years, she wanted to do that now. This was not something I wanted: I wanted a date a girl, see if we were compatible, be boyfriend and girlfriend for a few years and THEN get married and have children. Ultimately I decided to end things there, saying that it was nice to talk to her and that, while she was a cool person, I didn’t feel we were compatible. I then proceeded to block her on Snapchat & OKCupid, feeling guilty that I had led her on and then rejected her so suddenly and feeling dirty since I had was stupid and shared my sexual fantasies way before I had even met a girl physically.

This was a deeply uncomfortable experience and unfortunately its emblematic of several similar experiences I’ve had since I started dating four years ago. Many of the women who’ve been attracted to me over the years have wanted to move way too fast, wanting me to have sex with them and become their boyfriend or husband before we’ve had more than one date (or, in some cases, before we’ve even met in-person). Most of them a similar to C, having had rough childhoods and trauma. I seem to attract these kinds of people and I don’t know why. Is it because I get too personal in messages? Is it because I have a babyface and am not experienced, so people see me as innocent? Are these just the kinds of people that use OkCupid and other OLD sites?

So that’s my first question: How do I stop attracting people like this? How do I identify these types of people so I can avoid this in the future? What do I need to change about my behavior so I don’t lead on people and make the desire a relationship too quickly?

My second question is about what C said about it being obvious that I was a virgin since I was reluctant to flirt. This is not the first time I’ve been told this from people I’ve messaged on OLD sites. Now, I try to be playful and fun in my messages, and I try to compliment the people I message so that they know I’m attracted to them. Is this not flirting? I try to avoid sexual compliments and discussion when messaging on OkCupid to avoid being creepy, is this wrong? How do I message women without sounding like a virgin?

Thank you,
Mr.Slow-and-Steady

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