Anna David is the executive editor of The Fix, as well as being the author of Party Girl and Bought. Her newest book, Falling For Me, wherein she tries to follow the advice in Helen Gurley Brown’s Sex and the Single Girl, is due out October 11th. She’ll be telling us about some of her adventures in this new column, Sex and the Sixties Girl.

While bumping into a guy bringing another girl a drink, wearing a colorful pin and lying on a Checkers beach towel were all valid ways to meet men back in Helen Gurley Brown’s time, a lot has changed since the 60s when it comes to dating.

And when I say a lot, I mean we now have this invention called online dating—an invention which I was perfectly happy to let others enjoy. But I had agreed to change my life, embrace all that I had not been embracing and since that included online dating, I realized I had no choice but to try it out.

I get that it’s not that big a deal. I understand that everyone does it. I’m aware of the fact that we all know someone who knows someone who met the love of their life that way.

It still doesn’t mean it’s what I imagined myself doing. See, I have one characteristic that makes me an extremely un-ideal candidate for online dating: the fact that the most judgmental aspects of my personality are unearthed through the type of communication Internet dating demands. I mean, I’m someone who loses a little respect for friends when they can’t seem to determine if they’re supposed to be using “your” and “you’re” in emails and distance myself from those who can’t keep up the appropriate pace on an IChat. But I signed up anyway.

At first, it was just as I’d feared it would be: I was immediately assaulted by a slew of missives from men who all seemed to be a good decade or two older than me, lived in places like Newark, and loved car racing, drinking Pabst Blue Ribbon or other activities that horrified me. Many felt we’d make a perfect match—a sentiment they expressed with a sea of emoticons and even more spelling errors.

I tried to quell my judgmental side but I discovered that when it comes to online dating, I’m all judgmental side. The open-minded, accepting part of my personality just retreats into itself like a tortoise who realizes that this world isn’t all it’s cracked up to be and descends back into its shell.

But I ordered myself to cool it. What was wrong with a few spelling errors? I reminded myself that when I like a guy, he can say, do, or spell any way he likes and I’ll still like him. And this led me to a rather jarring conclusion: the person I was judging most harshly in this situation was me. Has it really come to this? I’d realize I was thinking as I scrolled through the site. How did we end up here?

Over time, the messages and profiles seemed to improve ever so slightly and I began to correspond with a few Match men. Some turned out to be okay, and two—later, down the line—were inarguably lovely (though not lovely for me to be with either anymore). The lovely ones don’t make the best stories, though. No, the best stories are about the ones that made me not only wish I hadn’t agreed to the date but also ruing the day I’d signed up for Match in the first place.

Greg was one of these. Greg, it should be noted, was wearing a hat in his Match photo. You’ll notice I didn’t say photos. I didn’t know then to be wary of those who post only one photo, let alone those whose one photo features them in a hat. Greg and I agreed to meet for coffee, a plan I considered a “pre-date” where we’d determine if we wanted to go out on an actual date.

Greg wore a hat on our pre-date. He also came across as funny and self-effacing. In retrospect I’m not sure how this happened but I guess we can all be anything for an hour. He was a banker—which, I’d decided ahead of time, was a good thing. My entire life, I’d really only fallen for one type—writers and actors—and I’d recently decided that this was the problem. I needed to force myself to like adults—men with fewer shrink bills, health insurance handed out by an actual company and financial jobs I didn’t quite understand.

When he asked if I wanted to go to dinner the next night, I agreed.

He needed to meet at six in the evening because, he explained, he worked banker’s hours, which involved getting up when it’s still dark out. I told myself that this was a good thing, that it’s healthier to eat earlier—that this is what adulthood is all about. He wanted to meet on the Upper East Side—as he pointed out, he’d come all the way downtown to meet me for coffee. The Upper East Side, I thought, was where the adults lived. So I made the trek.

When I first walked into the restaurant, I didn’t recognize Greg without his hat. He didn’t actually have the problem most hats are meant to conceal—a receding hairline or premature baldness. His hair was just plain weird. Parted in the middle, flippy. I felt shallow for being so bothered by the follicles decorating his scalp but his hair wasn’t really the problem. The problem, I realized a few seconds after sitting down, was him.

He opened the conversation by complaining about the taxes in New York. “The highest in the God damn country!” he crowed. I nodded; they seemed quite high to me, too. Then he tilted his head to the side. “Can I ask you something?” he asked.

I nodded. I was still trying to make sense of the hair, still wondering how on earth I’d managed to be charmed by him at coffee the day before, still contemplating how low my standards must be dipping for me to find myself in this situation, still trying to figure out if I could feign a sudden illness before we ordered our entrees.

“If it turned out it was too late for you to have kids, would you consider allowing another woman to carry your baby?” he asked.

Yes, reader, this is what he asked. This man whose hair I couldn’t stop staring at. But, as I said, it wasn’t the hair that was the problem. It wasn’t the question that was the problem. It was that I’d allowed myself to believe that what I was seeking was wrong—that I had to force myself to be attracted to men like him. I realized right then that I had to stop feeling ashamed of what I was inherently drawn to. If I only dated men who were incarcerated for beating their previous girlfriends or were chronically unfaithful, that would be one thing. But it was time for me to own the fact that I simply didn’t like bankers, or eating dinner at six in the evening or the Upper East Side or to be questioned about my willingness to have one of my eggs inserted into another woman’s reproductive system. Or even that I could be okay with all of those things if I liked the guy but this guy, with all of those things or without, was not for me.

And also, it was perfectly okay not to like his hair.