Yes, I took the plunge. After almost two months of being single I decided to try out this whole online dating thing. Don’t get me wrong, at this point I had met a few people at bars, the climbing gym, and on the bus (oh boy, is that a story) so the issue wasn’t really an inability to meet men. I never really felt I was able to fully put myself out there because of my job, my investment in friendships, and a pretty active lifestyle. Seriously, putting yourself out there is a bit exhausting and you have to deal with a lot of creepers, so at the end of two months I was emotionally drained from all the late nights at bars, interrupted reading time at coffee houses, and being propositioned by a ganga grower I sat next to for 30 minutes on the bus. It’s not like I am turning to online dating because I feel this desperate need for male attention or a relationship, I was more driven by curiosity since my only dating experience before now has been within a high school or college campus environment.

College: where you find boyfriends just by following the sound of a guitar.

I set up a profile last week at OkCupid; it is pretty quick depending on how much information you want to share. You slap up a few photos, list your favorites movies, music, hobbies, and even get down to the nitty gritty details like your height, body type, and how much money you make. I felt like I was placing an ad for myself on Craigslist (no, not like THAT you sicko) while trying to make myself sound like the coolest person ever. A few of the questions were hard to take seriously, so I didn’t. (“The most private thing I’m willing to admit,” really? You think I’ll type that up right now on the FOREVER INTERNET?)

Two minutes after I posted my profile I had six messages from willing suitors. Don’t call me a braggart, it’s just how the internet works. I’m willing to bet there are hundreds of people just in the Portland area logged into OkCupid trolling the market on an hourly basis, maybe even more frequent than that. You can message back and forth with a person on an instant message feature and I downloaded the app on my iPhone so I was already in the middle of ten different conversations on my bus ride home from work. Luckily there’s a handy “Block” feature where you can ignore the creepers that like to say “Hi” by offering you oral sex and their hairy bodies. <shudder>

My profile brings all the boys to the yard…

You can even view who has visited your profile (much like LinkedIn) and see with whom OkCupid matched you using their highly sophisticated algorithm. This is dependent on you answering dozens of questions about your personality, personal philosophy, political/religious beliefs, and sexual needs (these get awkward and very personal, like “Fifty Shades of Grey personal”). You are encouraged by the peeps of OkCupid to fill out as many questions as possible with the insistence that the more you answer, the more accurate the matches.

I set up a date with Man #1 for the next night. Yes, it’s that quick. I was so excited about this date because it would be the first somewhat “blind date/meet-up” I’ve ever done and I was determined to WIN (because everything is a game to me). You could say that I was…pumped…?

Rule #1: Meet at a common place. Don’t let a strange man pick you up where you live. That’s stupid.

We met at a restaurant for what I thought would just be “drinks.” I remember liking the way he looked in his pictures, he was a huge fan of the same kind of music and Arrested Development, and we had a lot of fun chatting over IM. When I walked up to him in the bar I immediately felt like an asshole because the first thing I noticed was that he was probably three or four inches shorter than he said on his OkCupid profile. I was wearing minimal heel-age and at 5′ 5″ I towered over him. I have a type, and they are at least the same height as me. He also liked to talk about himself. A lot. Too much. My mind was making this noise.

Rule #2: Don’t let yourself have high expectations. He’ll just let you down..

After a chat over a neat Buffalo Trace and three Blue Moons (yes, the latter were all his and served in conspicuous foot-long glasses with a giant orange slice) he said that he was going to check on our table. My heart dropped. I thought this was only “drinks” so I was actually on my way out as soon as my whiskey finished making its heated way into my belly. I was exhausted from listening to this guy obsessively discuss his job, his truck, and quoting lines from each and every Arrested Development episode ever made and I definitely didn’t want to sit through another two hours while we try to order food in a very busy restaurant. I sighed and downed my whiskey before a host guided us to a table.

Buffalo Trace: Is it in you? (It better be if you want to get through this date.)

Rule #3: Don’t be afraid to leave. It’s okay, really.

At this point I should have clarified with my suitor that I could only stay for one drink and then excuse myself for some other dinner plans. But I didn’t. I don’t know why. Yes, I do: I avoid confrontation as a rule, am a pushover for free food, and since he was buying everything I ordered another whiskey (he had another two Blue Moons) and stuffed my face with bread while he went on and on about his family origins from Western Europe. The dinner lasted two hours. Oh god, it was a loooooong two hours and I think I only said about a dozen sentences the whole time and that was difficult enough. I had to stay to fake my intention of splitting the check, but when it came he let the waiter talk him into signing up for the restaurant chain’s rewards program. If you are a man and reading this, do not ever decide that the right time to fill out an application for a credit card is while you are on a date. It’s tacky and it’s weird.

Rule #4: Don’t give your phone number to men if you’re not interested. It’s mean.

The date ended only with a hug (thank god, I didn’t want to have to starfish his face with an open palm) but he asked for my phone number. I am a people pleaser by nature and usually say “Yes” to things without thinking, so I gave it to him. This was not so smart, nor kind. I knew I didn’t want to date this guy. I knew I didn’t want to have to suffer through another moment of him listening to his own voice go on and on and on about the size of the rims on his truck. And yet, when he asked anxiously for my number after saying that I “was such a great listener” (you made it easy, buddy) I still gave it to him. This made me feel like a horrible person when I then ignored his texts for five days. If you are a man and a woman doesn’t text you back after receiving 20 text messages over the course of five days, she’s not interested, leave her alone.

So that was my first experience, but it’s not the juiciest or the creepiest or the scariest, so tune in for next time so you can learn from my horrible, stupid mistakes (I may or may not have gone out with a crackhead, still debating).