Trevor

When I was very young, I was best friends with a girl down the street from me. Her and I were inseparable. Unfortunately we often had to look after her bratty little brother Trevor, who was several years younger than us.

After losing touch with my friend years ago, you could imagine how shocked I was to see her little brother at an industry party last month. Turns out he has a job at an amazing company I would love to work at. I gave him my business card and asked him to let me know if any positions opened up. This was a mistake. For the rest of the night the kid followed me around trying to start awkward conversations with me while I tried to mingle with other industry professionals.

The other night I started receiving text messages him. Our exchange went like this:

Trevor: Hey it’s Trevor lol. What are you up to tonight?

Me: Just cooking dinner. You?

Trevor: I’m going out for a friends birthday. You should come!

Me: No, I don’t think that’s a good idea. Have fun!

Trevor: Why not? Just come.

Me: No, I think I’d like to keep you as an industry/business contact. Have a good night.

Trevor: Yeah, we can talk business over drinks…

Me: No, I don’t think so. Have a good night.

Trevor: I’d have a better night if you were here

Me: Please stop.

I figured that would be the end of the exchange but sadly I was wrong. In the morning I woke up to yet another text message from the kid.

Trevor: Brunch?

This time I chose not to respond. I guess that was a mistake because shortly after that I got a prank phone call. I guess if the kid continues to act like a child I might have to go an have a conversation with his parents.

Shane

About 2 years ago I fell in love. This was a first for me so as you can imagine, it literally ruined my life. Shane was a professional baseball player playing for my city. We both fell hard and for the time it lasted it was the happiest I have ever been.

Shane was not the smartest person though. When Shane went home for the off season we kept in touch through phone calls and text messages mostly. His crowning moment of stupidity came around the same time as our birthdays which happen to fall within 2 weeks of one another. In the weeks shortly after my birthday I was flying out to see him and thought I’d send him a preview of his birthday gift- a Victoria’s Secret lingerie bag. Immediately following my text to him I received a picture of a Tiffany bag. My birthday gift, right? Wrong. I showed up in his city and waited for him and my birthday gift, while wearing his gift in our hotel room. To my surprise he showed up wearing a Tiffany necklace that he has recently purchased for himself. It seems that in his mind, we were simply playing a game, sending each other pictures of bags. Like I said, not the brightest.

It was that same day Shane got a phone call from his agent letting him know he had been traded. Shane and I would no longer live in the same city. Our relationship ended shortly after that.

John the Holy

I am an atheist. You can imagine my confusion when a devout Christian asked me out for a date last week. On Monday I met John downtown at one of the newest tourist attractions in my city. The date was fine, simple conversation and the venue provided enough visual stimulation that awkward silences were kept to a minimum. The strange part came the day after. John the Holy asked me out on a second date. It was to my understanding that our date had left both of us feeling a friendship relationship would be more realistic than a romantic one. Apparently not. The shocking part of this all is that this guy is a virgin. He literally is waiting until marriage to “make love”. Now, without making myself look extremely promiscuous, I am not a virgin, in fact, I really enjoy sex. Now I can’t stop wondering why a Christian with such strong convictions would want to take out a non-virginal Jew?

Lately

Each year, the dates I’m taken on become less and less impressive. It used to be that a date consisted of being picked up at my door, taken out for dinner/drinks/movie and dropped off at my door with the chance of a goodnight kiss. So far this week I’ve gone on two dates. Monday night was with Luke, and Tuesday night with John.

Luke invited me to meet him for drinks downtown. Conversation was OK, heavily one sided but fine nonetheless. When we had both consumed enough alcohol to really make things interesting we agreed to call it a night. Our bill arrived and obviously I offered to pay half… it was to my surprise that he accepted. Now don’t get me wrong I am perfectly happy splitting a bill but I would never ask somebody out on a date without the intention of paying for the full bill. (And yes, I have asked people out before and paid.) He offered to walk me to my car and surprisingly went in for a kiss. If i wasn’t so liquored up I might have been quick enough to avoid his on-coming lip attack, but alas, I let it happen and headed home unimpressed.

 

Welcome to my life as a Serial Dater

Relationships? Few and far between. I’ve never been one to fantasize about my future with someone, dream of my wedding or make plans for a family. I am a serial dater.

It started when I was around the age of 14 and starting my high school years. Being incredibly social always attracted people to me but for whatever reason, only for a short period of time. Feel free to make your own conclusions as to why I still remain single and dating, but let it be known that my life’s goal has never included a significant other.

Enjoy