Normally when I’m writing about my online dates, I try to come up with a dating lesson or moral to the story like “don’t spit” or “don’t still be married” or “don’t email a guy for five weeks before you meet him”. But with my next date, Simon, there isn’t one thing that I can point to as to why we didn’t work out. I wasn’t really overwhelmingly physically attracted to him, and he pulled a couple of jerk moves, but I can’t narrow it down beyond that. I can say for certain, though, that if you refer to a guy as ‘The Schlub” to your friends and family, well, he probably isn’t the man for you.

Simon had one of the best dating profiles I have ever seen. It was witty, funny, his pictures were good and wide-ranging. I just liked the whole vibe of it, so I sent him a short email referring to a drink he had mentioned liking. He emailed me back almost immediately, we exchanged a couple of emails back and forth and, before I knew it, we had agreed to meet for a drink at a bar in my neighborhood. I was pretty excited.

I got a text from Simon that said he was waiting for me at the bar and, when I walked in, I knew exactly who he was from his pictures. He had not misrepresented himself, and he was pretty cute; not crazy cute, but close enough. We had a drink and actually had a decent conversation. Simon was very smart and sharp, and I was on my toes keeping up with him. As we talked, though, I kept asking myself if I was attracted to him. Like I said, he was not unattractive, but there was something just…unkempt about him. His clothes were somewhat dirty and wrinkled, his fingernails were kind of long, and his hair didn’t look like it had been washed in awhile. He didn’t have a ball of dust over his head ala Pig Pen, so when he asked if I wanted to move on to another bar and get some food, I agreed. Maybe another drink would help me figure out if I was attracted to him.

One lesson that actually can be gleaned from Simon is to watch how much alcohol you consume on a first date. We ended up at one of my favorite bars, with my favorite bartender, and–before I knew it–I was feeling like I had imbibed perhaps a bit too much. Before it got out of hand, though, I said I had to be going and Simon offered to walk me home. We were still having fun. He was pretty hilarious, and he had totally chatted up my bartender. So I agreed. Damn you, drinks, damn you.

Ten minutes later, we arrived at my apartment, and I told Simon that I had really liked meeting him and gave him a kiss. He kissed me back, not in a timid fashion, and said, “You know you want to invite me upstairs. You know you do.” Oh, MAN. No, no, no, no–I really did not. I just wanted to end our evening, sober up, and meet up again later for another date. I suggested to Simon we should perhaps wait at least (at least!) another date before he came upstairs, and he did not like that. I know that we had both had a few drinks, but after Simon asked me three more times, I was a little peeved. I just turned around and left him there on the street. Great way to end a date. Really.

I didn’t hear from Simon that night, but the next day I got numerous texts from him apologizing profusely about what had happened. He really, really liked me and wanted to see me again and, he promised, he would be a gentleman and neither of us would have too much to drink. I was a little hesitant, but I had liked Simon and I was not blameless as to how things had ended, so I agreed to meet him again.

Simon and I went on a few more dates and met a couple of times for drinks and football. It was during this time that ‘The Schlub” moniker came into play. Simon always looked like he had rolled out of bed with messy clothes, crazy hair and bad breath. I was just not attracted to him. He also started to develop this irritating habit where he would text me endlessly about any number of random subjects, often really late at night. I was at the point that I just wanted to him to leave me the hell alone. It says a lot for his personality that I hung in as long as I did.

On the last date I had with Simon, I agreed to pick him up after he got two sleeve (covering his whole arm) tattoos because he couldn’t drive after having them done. When I arrived he had gauze covering both of his arms with a layer of plastic then wrapped around the gauze. Holy sh*t! What an ordeal. We went to dinner, and that was…fine, but I was definitely sure I was not into Simon. I dropped him off at home, kind of relieved that our date was finally over, when he asked if I would come in, help him unwrap his arms and he could show me his new ink. Damn. How could I say no and, really, part of me was dying to see what his house looked like inside. Would it be a dump?? Would it be like an episode of ‘Hoarders’?? I had to see for myself.

Surprisingly, I loved his house. It was immaculate, and he had amazingly cool artwork all over. I was still looking around, a little awed, when Simon started unwrapping his arms. It should be said that I LOVE tattoos on a guy, especially sleeve tattoos, so I was pretty excited to see how his looked. As they slowly became visible, I wanted to die. I hated, hated, hated them. They were some of the ugliest tattoos I had ever seen, but I could not let my feelings show. He was going to be looking at those things for the rest of his life so seeing a look of horror on my face would most likely harsh his buzz.

Luckily it was a work night. I was able to get the hell out of his house before he figured out that I found his arms to be cringe-inducing. We kissed goodbye and, as I walked to my car, I knew I was d-o-n-e with Simon, even if his house wasn’t as dirty as he was and he could make me laugh. It was just not there for me, not at all.

A couple months later, I was a guest on a local podcast that Simon and I both loved discussing, of all things, online dating. We still had contact every now and then so I texted him in excitement and he, very nicely, told me how thrilled he was for me. I showed up to record the podcast, though, and, as the producer walked me back to the recording booth she asked, “Do you know someone named Simon? He emailed me to tell me what a sweet, awesome girl you are and then he wrote three paragraphs about how he had blown it with you.” What, what, what? Of all of the people in the world, he had to unload on this poor podcast producer? My god.  Thank the lord I had dodged the Simon bullet in all of its dirty, unkempt glory.

Posted on by Kate in The Dates

One Response to Simon

  1. Pingback: Meet my next date Simon otherwise known as “The Schlub”! | Dates With Kate

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