The perils and misadventures of online dating in No Fun City, with bonus date-stalking tips from a tech-savvy single lady.

I’ve just completed watching seven seasons of Gilmore Girls. The entire series. And it’s not even on Netflix. Watching this much senseless banter (mixed with alcohol) seems to be my only distraction from the fact that I’ve just ended an eight-year relationship.

Let’s just put this into perspective: the last time I was single Facebook didn’t exist. We found our apartment in the newspaper. The paper paper. And online dating was reserved for the dregs of society. Most of my friends say this isn’t true anymore, but obviously I’m hesitant. Actually, I’m hesitant about dating again in general. Telling my life story to a bunch of new guys sounds tedious. You know that person, who tells the same story over and over like you’ve never heard it, but you just have to grin and bear the awfulness? I fear I will become that person except the listener will be me, and I’ll be torturing myself. At least with online dating you get all the basic questions out of the way on your profile. And it does seem to be the most cowardly way to get back into dating, which is appealing. What do I have to lose?

A friend of mine told me never to message first. She says that guys are genetically predisposed to love the hunt and it’s our duty to allow them that privilege. She also employs this strategy by ignoring texts and emails from any guy for anywhere from 8 to 24 hours. Apparently common decency is old-hat. I have so much to learn. I scratch together my profile with the cutest (ahem, er, photoshopped) photo of myself I can find and wait. Almost immediately, I get an enticing offer:

“I want to clean for you, be your house bitch like, scrubbing your floors, toilet, doing dishes, dusting, doing laundry, ironing, etc… on my hands and knees under your control. I am not looking for sex, I want to be your slave.”

Ummmm, jackpot? Why shouldn’t I take this guy up on his offer? I really do hate cleaning. And I could still date other guys, right? He would probably love that because it would be even more humiliating. I’d be making out with some guy and he could be vacuuming. “Oh him? No, he’s just my slave, Ralph. Ignore him.”  Actually, that might be awkward. And I love being a bitch so this is surprising. I think I’m more afraid that I’ll like it and then I’ll be stuck craving this sort of arrangement. I feel bad for people who need such elaborate set ups to get off. Autoerotic asphyxiation, infantilism, plushophilia..etc; it all just sounds like a hassle (and possibly life threatening). Pass.

I get why you can see when someone has viewed your profile on these dating sites, but it also makes obsessing hard without looking crazy. It’s also really hard to keep everyone and their information straight: was this the guy who enjoys yoga, or yodelling? I need to click on that profile to find out – over and over again. So I’ve devised a simple and effective method that doesn’t involve paying the “stalk anonymously” fee. First, screen capture their profile (if you don’t know how to do this, Google it). Second, save all their photos to a folder with their name on it. And lastly put that folder in your dropbox so you can access and scrutinize their photos from the comfort of your own palm or wherever you like. I’m a genius. You’re welcome.

I get another message. A funny, rambling message, but rife with spelling errors. This is unfortunate. If you don’t spell check, how much do you really care what I think of you? The occasional error is fine, but peppered throughout the message and I think you’re a meathead. Don’t I deserve someone who can tell the difference between their and they’re? But I’m trying to be less judgemental. My shrink says I gotta go easy on these guys cause I’m too picky. So I give the guy a chance cause it seems like the decent thing to do and he has a really good head of hair. We’re messaging back and forth and it’s nice. Having something like that to look forward to is exciting. Then I get my first piece of evidence that enables me to find out his real identity and I’m on Google as fast as humanly possible.

I only have his first name and what he does but ding ding ding, I find a video! That’s like the Holy Grail for Google stalking. I press play nervously. He looks okay, albeit older and chubbier than his profile photos would suggest, but he has a nice coat on and it’s not horrible. I immediately forward this to all my friends, of course. With their blessing I keep talking to him and that’s when I got the message that should have been my cue to exit.

He tells me a story about his childhood and brings up his past flagrant use of the “n” word (though he spells it out). He says he admits it was horrible but I gotta ask myself, WHAT THE FUCK?! Even if you did use it and now regret it WHY ON EARTH would you bring it up now? In an email TO A STRANGER you may want to sleep with?

I ask my panel of friends and there’s a lot of air sucking, but he seems clueless about this being bad form, maybe it was just his weird attempt at humour? In the spirit of trying new things and being forgiving of people’s stupidity I send him back this message: “Well, my general rule of thumb has always been not to drop the N bomb until at LEAST the 3rd date.”

So I end up meeting him. I arrive at the coffee shop and he seems nervous; his hands shake a bit as he sips his coffee and I’m instantly turned off. Plus he was wearing a jaunty scarf that emasculated him further. I try to have a conversation with him but he mostly talks about himself. Then, somehow, he gets on the subject of people “not from this country” taking our jobs….fuck. This guy actually IS RACIST. I should have seen that one coming, I know. This is my first date in eight years, cut me some slack. My eyes dart around for the nearest exit.

During the weeks we were talking I felt so sure it would work out with him, and this alarms me. I don’t know how to date. Not that I thought it would be easy but I don’t seem to have any sense around this subject. How much should you put up with and when are you just being too picky? I’m just going to have to find something to learn from this first experience. Like, don’t pin all your hopes on one person. Or, if he uses the “n” word, he’s probably not marriage material.