Sometimes a Bad One Slips Through the Cracks

Today’s guest post is from my friend Jess Downey. Jess blogs regularly at All the Single Ladies for Chicago Now.

Sometimes a bad one slips through the cracks

When I first moved to Chicago people still searched the Yahoo member profiles to find people to chat with. For years, even though I had changed the location in my profile, I still continued to pop up in searches for Indianapolis where I used to live.

A little over a year ago, a guy randomly sent me a message about how I was gorgeous and he was interested in chatting with me. I told him that I was living in Chicago but it didn’t bother him at all. He seemed interesting and he was extremely attractive so who am I to argue? We continued to chat for a few months and talked about everything. As weird as it sounds, I felt like I knew him. That is, as much as you can know a guy on the internet.

We talked about tons of things. He told me that he was divorced and had twin daughters. And somehow we ended up having this whole conversation about how I am taller than many of the guys that I go out with (I was actually taller than him) and I told him about a friend that I had at the time who was even taller than I am (I think she’s around 6’2).

Of course, as we chatted we became more curious about each other and wanted to meet. I don’t have a car and Indianapolis is definitely not a day trip sort of thing so he volunteered to come to Chicago for the day to see me. Clearly I was interested in him so I agreed and we planned a meeting. The idea was to have dinner, maybe a few drinks and just hang out.

He came to my place to pick me up at my apartment and he was literally only there for a few minutes before we had sex. Honestly, I have no idea how it happened. Wait, technically I know how it happened it’s just normally I like to wait a little longer before getting that physical with a guy.

Anyway, we went to dinner and out for drinks and it was one of the best times I’ve ever had with a guy. His in person personality was pretty close to his internet personality so I felt incredibly comfortable around him. It ended up being really late so I offered to let him stay the night at my place. We really didn’t sleep all that much but ended up talking and having sex well into the morning. And I will be the first to admit that I kind of liked this guy.

As we were laying in bed in the morning he talked about how he liked me and thought I was pretty fantastic. He also threw in a few comments here and there about how awesome our little romps were. Apparently he was really into the fact that I was a tall woman. Then he casually mentioned something about wanting to have sex with my 6’2 friend. I wasn’t sure if he was serious or not and I think he sensed that I was annoyed so he dropped the subject and we went to have breakfast.

After breakfast he was getting his stuff around to leave and the subject of my 6’2 friend came up again. This time it was obvious he was dead serious. I mean he actually came out and asked me to hook the two of them up. He even went so far as to ask me to give him her number, to which I obviously declined.

Honestly, I wasn’t sure what to say at this point so he left to go back to Indianapolis. Then a few days later he sent me a message online and against my better judgment I responded. We made small talk for a few minutes and he apologized for not sending me a message sooner but he ended up going out of town to spend time with his wife’s family.

I think I read over that message 100 times to make sure I was actually reading it correctly, but there it was in black and white “my wife’s family.” Of course I confronted him and I am pretty sure he realized he outted himself because it took him forever to respond. And then he confessed that he was in fact married and not divorced as he had previously mentioned. Actually he wasn’t even close to being divorced, I mean not separated or anything.

At that point I didn’t know what to say so I told him, in a pretty harsh way, that we no longer needed to talk. He said that was fine and I didn’t hear anything else from him. That is, until a couple of weeks later when he decided to make one last plea to hook him up with my 6’2 friend. Apparently he felt that this was his one chance to “nail a woman that was that tall” so he was really hoping I could “help him out” (yes those are all direct quotes from him).

A million things went through my mind and I wanted to say each and every one of them to this guy but I knew that it wasn’t going to do anything and that he would probably continue to send me messages. I mean, the guy already lied about being married, cheated on his wife and asked to have sex with my friend while we were still naked without remorse. What was next? So I blocked him.

To this day, I have yet to hear anything from him and I often wonder how I was so wrong about this guy. I feel like I am a pretty good judge of character but I guess some people are really good at hiding things. I guess sometimes no matter how much you try to look for the signs, some people just slip through the cracks.