On-Line Dating Advice for Strange People

All of these lessons were learned the hard way.

#1 Always hug your date at the end and get their phone number if you were interested.

This happened because during the date we both agreed to meet at a friend’s party the following weekend. When I said, “Let’s meet up at the party next Friday”, I should have said, “Let’s meet up at the party next Friday. As this is our first date and I don’t really know you that seems like a safe place for a second date after our delightful brunch.” I did lean in for a hug but it hit that awkward chasm where neither of us were quite close enough and I bailed at the last second. I zapped her a friendly facebook message wishing her a good week a few days later. She refused to speak to me.

#2 When meeting new dates at parties, make sure she isn’t best friends with the woman you didn’t call.

I realized my horrible mistake a few days after swapping phone numbers and friending her on facebook. A quick perusal of her photos and not only did I realize she was friends with the first date, they were into besties territory. I’m a quick learner so I made sure to hug and call often, but that seemed to make things worse. After the second date ended with the woman who taught me lesson #1 joining us for drinks, I decided to match their awkward social situation with an extensive explanation of spatial story telling in Bethesda Games. Never heard back from either after that.

#3 People don’t actually mean they like hiking when they say they like hiking.

I love the outdoors. Mountain biking, camping, or hiking are all things I love doing when the weather permits. The problem is that most dating websites will frame this question in terms of, “Do you leave the house occasionally? “ or “Does sunlight hurt you?” Nobody wants to click that they don’t like hiking and it seems like a fun thing to say. Right up until you’re pulling out a map and explaining a 15 mile vertical climb that is a 4 hour drive away.

#4 It’s usually a bad sign if they cancel a date four days in advance because they’re too tired.

One of the trickier problems that crops up is dating people who are too nice to be dating online. An overly nice person doesn’t really want to do the rejecting or hurt anyone’s feelings. So if you’re really into them and they want out, prepare yourself for a long and awkward period of never-returned calls and cancelled dates. If they stand you up once, shame on them. If they stand you up twice? Shame on you.

#5 Watch or read something the average person can relate to.

On one date we were chatting about media and I realized I had been on a bad obscurity bender again. Between my job, rewatching old sitcoms on Netflix, GOG.com, and reading bizarre academic papers I did not have a single thing to say that the date would have any interest in. After a bit of pestering I finally just started talking about my latest crackpot theory about rules and video games. She was quiet when I finished and asked me how I related to people if that was what I did for fun. I told her, “I don’t really, I go on internet dates.”

#6 Joking that you’re going to get a dog if Match.com doesn’t work out can be easily misinterpreted.

It doesn’t make it any better if you say you’re kidding and that you really like cats instead.

#7 When dating multiple women with the same first name, organize them by their last name.

G-chat, cell phones, facebook, all of it. Apologizing will not undo this one.

#8 Don’t do dinner on the first date. Just meet for drinks of some sort.

There isn’t actually any story behind this one, just pure statistics. Every girl I took out to dinner on the first date ended badly eventually. Drinks, be it beer or coffee, ended the best and we’re still friends. Well, I don’t wish something bad would happen to them. Lunch always ended up somewhere in the middle.

#9 If two dogs are fucking in a truck next to your outdoor table on the first date, just let it go.

After realizing the giant Labrador had enough in him to last all day, I just ordered a beer and asked her if she was familiar with The Wire. She said no and talked about herself for the rest of the date. The dogs stared at me the entire time.

#10 It’s okay to ask them out more than once.

I base this on the fact that most of the messages women receive on dating websites are incoherent, creepy, and often just asking for sex. If you’re writing a grammatically correct, polite message that comments on several things you have in common and invites them out for coffee somewhere, that’s okay. You don’t need to send it every single day, or even every week, but people are busy and things change fast with internet dating.