A couple of Saturday’s ago, as usual sitting around waiting for something to happen I get an alert on my phone that I have a new message on the dating website. I had slowed down all dating activity for the most part. The message turns out to be from “Donna”. The first woman I went out with on this site, which turned out to be a nightmare. I received a number of messages from her over the couple of months since that date. I ignored every single one of them. Most of them just said “hi”, while some read: “Why are you ignoring me?”, etc. She finally stopped for about a month and then I get a two word message from her that just says “YOU SUCK”. I’m not really a mean person, but sometimes I have to be I guess. This is how the rest of the exchange went:

“Wow, thanks”


“Look, it didn’t work out after that one date and I moved on. Sorry if that was wrong of me”

“OK then”

“So Donna, have you had any luck on here since our date? I haven’t”

“Well that’s UR Problem NOT MINE”

“Good luck being a drunk, lonely older woman forever Donna”

And then I blocked her.

For the most part this online dating thing is working. I have gone on dates. Most of them have been less than one time deals. It’s getting a bit exhausting at this point really. There’s only so much talking about yourself you can do, only so much listening to someone else talk or write about themselves you can take. Some of the messages out of the blue I get are painful. I feel like I have become shallower than ever. I like to think I am meeting people for practice, or because of some eventual time when I meet someone I really like I’ll suddenly be “ready”. What it all boils down to is I’m bored. I like hanging around with women more than men and, well I’m bored. I am not in any place to be in a relationship with someone. I most likely never will be. Even writing to women on there, after a few days you start writing each other more frequently and then start to know each other’s schedules and that kind of thing. I don’t want anything to do with that. It’s nice to share certain experiences in life with people, and obviously it’s nice to get laid, but really, I’d rather just be doing my own thing without having to “check in” or wonder where some girl I call my girlfriend/wife is. That sounds horrible to me at this point. Okay before I get too serious here…

I started talking to Jill on the dating website right when I started using it. It was really hard to talk to her as she would send these one-sentence responses to me and couldn’t keep a conversation going. I kind of forgot about her and then noticed her online one night and sent her a message asking how her search was going. Asking this seems like something everyone asks each other there. Usually when I ask someone I am trying to gauge how bitter she might be at that certain time. If they are really at the end of their rope it’s going to be harder to get a date. From what most women on there tell me, and from what most women I know in real life tell me, men are idiots. They have no idea how to talk to women, they say disgusting things right off the bat, assume women love photos of penises, etc. I never do this, and I’ve never sent a photograph of my penis to anyone via my phone…that didn’t ask me to. I have to say trying to photograph your penis with an iPhone in your mother’s bathroom at 5:35 AM is a skill every man should learn at some point. This is what I have heard anyway. I’m not some sort of gigolo with “THE PUSSY WHISPERER” airbrushed on the back of my Chevy or anything, but I like to think I can talk to women and generally am interested in things they have to say…well as long as they aren’t playing the “do I look fat?” game.

So Jill and I start talking and she is now more talkative, and admits that she is “shy at first” We exchange phone numbers and text for a few days straight. At one point, after a week I see on my phone I have a missed call from her. This is followed up by a text message. “Sorry, I accidentally called your phone! LOL” I guess we are at a text only situation. A few days later I suggest talking on the phone and through some miscommunication I assume she doesn’t want to talk on the phone. We continue texting for another week. In the meantime a new woman starts talking to me, also named Jill. At one point she gives me her phone number. I have no idea what either of their last names are but don’t want to put “JILL 1”, “JILL 2” as the contact names. I end up just putting “Jill” for the first “text only” Jill and leave the other one blank. In a year from now I will most likely have no idea who either of these two women are so what the fuck does it matter really? Finally the first Jill and I speak on the phone and arrange a date. Well, to hang out.

Jill lives in New Hampshire, about an hour from me. She lives with her son (11) and her brother (38), while he “gets back on his feet” The father of the son is homeless and has one leg. When I tell my friend about this a couple of weeks prior she tells me to “run away”.

“Are you fucking crazy?” I ask her

I am going to head up to her place on a Friday night and hang with her and her brother and the woman he met on the very same dating website. Oh yeah. So when Jill and I started talking she mentioned her brother seeing this woman he met from the same website. She showed this woman a picture of me from the dating site and she claimed I wrote her. When I arrive at their house, low and behold I recognize her as a woman I sent a message to.

I make plans to hang with the other Jill on Sunday afternoon. When I pull get off the exit to go to the first Jill’s place I note there are two towns listed on the sign that I am heading to. One is where Jill lives, and the other one is where the other Jill lives. I have to come back here Sunday.

The house they live in is a two family house with a huge yard. When I pull into the driveway I am immediately confused as to where Jill is. She ends up looking a little different than her pictures, but not much. Also, I have recently as of this summer realized I might need glasses so that might have had something to do with that as well. She greets me, and there is a younger skinny girl (upstairs neighbor) standing there, a guy (brother Billy) sitting on the porch with his date (Brenda). There is also a little Chihuahua running around and a little boy (the son) off in the distance. Everyone is smoking aside from the child and the Chihuahua. It seems as if for the remainder of the night there is always at least two cigarettes burning. Jill introduces me to them and then immediately mentions “See that’s Brenda who you wrote to”. I make eye contact with the brother and now I’m pretty uncomfortable. The brother is a normal looking New England type guy. He is wearing a New England Patriots shirt, has a goatee and is just New Hampshirey. He turns out to be a pretty nice guy. They are all really nice people.

We sit around a fire pit. Jill to my left, her brother to my right, Brenda to his right and the neighbor comes and goes throughout the night. Her boyfriend arrives at one point and he is an okay New Hampshirey guy as well. While sitting by the fire a radio plays a classic rock station that is playing some of my favorite music, and of course Billy has to call out the band every time a song comes on. I only correct him twice. He is wrong five times.

For whatever reason, I quiet myself into a personality that must have left little to be desired. I think we had talked about everything we could talk about those few weeks getting to know each other before meeting. This was the end result. Two people sitting there barely talking to each other with other people around to make it a little easier. Obviously everyone there must have noticed. I had three cans of Budweiser over the five or six hours I ended up hanging out. At one point while putting my beer can down in the tall grass to the left of my seat I secretly dumped out half of the beer on the ground. I don’t really like beer or alcohol that much so it’s usually a chore to get through a second beer, and a third one, forget it. I didn’t want to look like a pussy that doesn’t finish his beers.

Once they grew tired of some of the deeper cuts on the radio a laptop was brought out and we listened to some Pandora stations. I then learned that one of Jill’s favorite bands is Matchbox 20. I don’t think I’ve ever actually heard Matchbox 20. I mean I am sure I have but according to my friends on Facebook I am supposed to not like them or Nickelback, another band I’ve never actually heard. Thankfully the band names are so awful that I already just don’t like these bands on that alone. So we’re listening to some truly awful music I’ve only heard of. Shinedown. Disturbed. The Sick Puppies. There is apparently a band called the Sick Puppies and it’s not a punk rock band from 1981. “You like rock music and you’ve never heard of the Sick Puppies?” Jill asks me. I shrug. And then Kid Rock comes on.

An hour later as I am pulling into my driveway a little shy of 5:00 AM I get a text from her “You could have given me a longer kiss than that”. She is referring to the peck I gave her five minutes after the Kid Rock song ended.

“Oh we hit it off?” I thought to myself.

Later that afternoon I call the other Jill on the phone and cancel our Sunday date. I need some time to myself on a Sunday. That’s what Sundays have always been: for me and that’s how I want them to continue to be.