I’ve never had what you would call a ‘real girlfriend’

Hi Meredith,

I have never been great when it comes to talking to women, so I decided to join a dating website about six months ago. Things were slow at first but as I got more comfortable with the process, I actually began to meet some great matches. I have gotten the chance to meet a handful of them in person, and overall, the dates have gone well. But I keep running into a roadblock that I don't know how to get past.

When my dating history comes up, it seems that theses girls lose interest and I never hear from them again. I am a 30-something virgin. I've never had what you would call a "real girlfriend." I was always good with making female friends, and have lived much of my life in the "friend zone." I treat each woman I meet with respect, and understand that each may be looking for different things. But when it seems like things are going well, my dating history, or lack thereof, comes up and then they are gone. I'm wondering why my lack of experience is an issue for these women, and how can I talk my way around the issue when it comes up without lying. I'm not against premarital sex, but I also don't want a one-night stand. Am I out of touch with the modern dating world?

– Sexless In The Suburbs


I can make some guesses about why these women are put off by your sexual history (or lack thereof). Maybe they fear being your first – because they assume you'll require a second and third. Maybe they're concerned that sex with you would have to be a monumental emotional experience. That's a lot of pressure.

All of this is why your second question - the one about disclosure – is so important. You need to know that telling the truth doesn't have to mean disclosing all of your secrets. You wouldn't ask these women to share details about their sexual histories, right? You wouldn't expect to be told who they've slept with and why. You can tell these women that you've never been a big dater and that you spent your early years navigating the friend zone. Leave it at that.

As you date, focus on getting to know these women, and think about why you're having a good time. Don't let sex take over your brain. It's part of the dating process, but it's not everything.

– Meredith

Readers? Would you expect to be told, and if so, when?