In 1998 the Internet was an awful place. Well, in retrospect it was. I can’t recall what was on the Internet at the time but I kind of remember it like this:  Free e-mail, online forums where people gave their horrible opinion on everything, pornography, chat rooms, pornography, news, pornography, personal websites where people would put up links to places like “YAHOO.COM” among pictures of their car, some sort of horrible flash thing that played music, and a giant stat counter in comic sans (that usually read “044”). Somehow though, I managed to meet some women. I can’t remember the format of Yahoo Personals in 1998 or if that’s what I had, but I ended up meeting a girl from the South Shore named Ann.

Ann was from Florida; this should have been my first sign that this might not be the best idea; also she lived on the South Shore. I lived on the North Shore. I remember we exchanged pictures. I’m not sure how though. I didn’t have a digital camera at the time and who knows what picture I may have sent her. I do remember seeing a picture of her and thinking she was okay looking.

I was not really a bar person and the relationships I had been in up to this point were mostly via friends of friends and that kind of thing. The idea of dating women from the Internet sounded interesting to me. In my opinion you could at least spend some time getting to know each other. I don’t necessarily agree with this at this point. Tone in writing is hard to read in small grammatically challenged text messages and brief one and two line chat conversations at this point. I have experienced a number of let’s-call-them-disagreements because the tone of a message was read wrong. It truly is just better to talk to a human being face to face. I was kind of a pussy though. This seemed easy to me, less stressful.

Ann and I talked on the phone and she had an accent that was a dead ringer for Jodie Foster. Some of the things we had in common: we smoked marijuana, we smoked cigarettes, and we were single.

After a few conversations we decided to meet. I would drive down to her place on the South Shore, which frankly, is a pain in the fucking ass. At this point in my life, to drive to the South Shore for a date I would have to be put up in a hotel for the night, and the date would have to look like Marcia Brady, or Joyce DeWitt. Like most women I’ve ever dated, Ann lived in one of those ugly two story brick apartment buildings. This may have been my first visit to one of these “single woman with cat(s)” apartments that I would frequent for years after.  These apartments are all the same at this point. The same furniture in every one, no remnants of past men, a few cat toys strewn about on the floor, a number of CD’s that sit on a shelf writing a biography for your eyes.

Ann greeted me at the door and gave me a little hug. She was kind of dressed like a dude, or a lesbian. A flannel shirt with a tank top under it, jeans, you know. I met her cat and as it turns out the cat ended up being a little more interesting. I did not know the area so I had her direct us to places to eat and whatever other place of interest we needed to see. I went out with Ann four or five times. Each time we hung out a dinner was involved. Each time she ordered a chicken finger dinner. Four chicken finger dinners in what, a two-month period? A red flag went off after the first chicken finger dinner. I mean, really? Chicken fingers are great and all, but you should never eat a plate of chicken fingers in front of another person. If you are ever in a situation where you are eating a chicken finger plate in front of another human being you are probably on your way to a NASCAR race, or somewhere in New Hampshire.

On this first date we went to eat at some chain place where it was a long non-conversation about nothing at all. As it turned out we had all the conversations we would ever need to have over the phone. Ann was painfully shy and a pretty boring person. After dinner we drove around the South Shore, which was okay. It just looks and feels like the North Shore except you have no idea where you are going. The beaches seemed a little better. We made our way to a beach and walked and I had a one-sided conversation. She suggested we go back to her place to get high. We go back and end up playing with her cat for a little while. Her talking to her cat bums me out a little bit. She had recently moved to Massachusetts from Florida to deal with an ill grandmother and stayed. I don’t think she had many friends beyond that cat and “some of the folks at the call center” How many lonely chicken dinners on Friday nights with the cat, five hundred cigarettes and a sink full of an odd amount of dishes has Ann endured?

Ann suggested we play Yahtzee. For a minute I pinch myself and wonder if I just woke up at my aunts house in 1981, but no I’m here in the present on a date with this new girl, high as a kite on a couch…about to play Yahtzee. The Yahtzee ended up being a little more fun than I had remembered. I mean, not as fun as sexual intercourse, but it was a first date anyway.

We had a few more dates. She ended up being a little more talkative but us hanging out turned out to just be someone to get fucked up with and do some adult, non-Yahtzee type stuff…an hour away from where I lived. What tiny little spark we had kind of faded out before it even ignited really. At one point I went away for a week trip and when I came back I remember her telling me she really missed me and I made some sort of cold comment. Shortly after maybe the fifth time we hung out I broke it off with Ann…via e-mail.  The only way I guess I can justify this is it was early on in the life of the Internet so maybe I didn’t know this was a weak move? Yeah that’s it.

This would be my first of a number of “Internet dating” situations I’d get involved in. In retrospect most of them were good. The longest relationship I’ve ever been in (7 years) was with someone I met online and we are still good friends. The last real serious but brief relationship was also with someone I met online. The difference between these relationships and these random dates is that I met the long-term women without the dating stigma attached at first. It’s pretty impossible at this point, at least for me, to get thrown in the fire with a new person and adjust to their life and my life. It’s harder at this age as well since most folks are pretty much how they are going to be forever. Some of my close friends have suggested that I go on more “bad dates” like my first two I wrote about because they gave me material to write about. While this sounds enticing I don’t really have it in me to purposely seek out women I know I am not going to get along with just for something to write about. It’s obviously shallow and I’m not necessarily made of money to go on a bunch of bad dates. Well then, there are still more of these.