I’m going to a good friend’s wedding this weekend. And now I have men (boys) on my mind, which hasn’t happened in quite some time. In fact, I’ve pretty much steered clear of them for over a year now. After my first two years of dating in New York, I figured it would be wisest to take a timeout.

Since I only have about three months left in the country, I seriously doubt I’ll be dating anymore in NY. But I thought it would be fun (sad) to reminisce about a few of my more interesting (tragic) dating experiences. More than once I’ve been told, “I’m pretty sure this is the type of thing that only happens to you.” And for every other woman’s sake, I hope that’s true.

1) Mr. Demanding

I met this guy during an event at an art gallery. He was attractive, pleasant, and seemed smart. So I threw caution to the wind and took him up on an offer to join him and a group of his friends at an after party. I had a good time. He even paid for my taxi home. And since we worked in the same neighborhood, I agreed to have lunch with him the following week.

After a decent falafel lunch, I thought I might actually have an opportunity with this one. Walking me back to my office, he wanted to make plans for the next date. For some reason I couldn’t make concrete plans at the time – maybe I was going to be away for a few days, or something. But less than an hour later I received an email trying to firm up the plans. Now although I don’t remember why I couldn’t make plans at the time, I do remember that an hour didn’t change the circumstances.

I ignored his email and his follow-up phone call. Later that night I made plans with him for a later date (maybe a week). During the course of the week, I received texts, emails and phone calls – all with the presumptuous tone of a boyfriend. It became uninteresting and stressful. His emails were constant. He was upset with me for not immediately returning his phone calls. He barely knew me, yet he wanted me to make a commitment to him. I canceled the second date before the week ended.

2) Mr. Privacy

Not too much to say about this one. He was married. But the reason he didn’t tell me right away: he didn’t talk much about his personal life.

3) Mr. Insult Meany Pants

This one was a set-up. I haven’t been on too many blind dates. But I’m pretty sure this was the worst. Before we met, we spoke on the phone. During the course of the conversation he told he was shocked that I had never met anyone with his name, since I was “afrocentric” and all. He made fun of me for having a car. And he made countless assumptions about me because I was described as being “natural.” He said, “oh, I have you all figured out.” There’s not much that I hate more than being put into a box and prejudged. And if he had actually figured me out, he would have known that I already hated him.

Against my better judgment, I still met him in person. We met in Brooklyn and I drove, agreeing to pick him up from some corner. As I looked for a parking space, he commented, “it’s probably going to be hard to find a spot since people like you all bring their cars from California.” Was that supposed to be funny?

Against my better judgment, I got out of the car with him. But since I hated him even more now (and also was not attracted to him), we didn’t have the greatest conversation. It continued. But it was forced. At one point I mentioned having a sister and remarked that we have the same sense of humor (she’s hilarious). To which he responded, “oh, you have a sense of humor?” Finally giving into my better judgment, I ended the date and we never contacted each other again.

4) Mr. Flask

This guy I liked. We went out a few times before I invited him to my place. We were going to watch something. So I was prepared with snacks. I told him to bring something to drink.

The tone was immediately established when he was upset with me for not having dinner made for him. “I thought you were going to have a big spread ready for me.” Now since I barely cook for myself, I’m not sure what gave him that impression. But he ended up combing through my fridge and cabinets to come up with some crazy plan for a veggie burger. And though he briefly stepped aside expecting me to make it for him, I made it clear that he was on his own with the project (I was too busy counting down the minutes for him to leave). After creating his veggie burger, he pulled out a flask and fixed himself a drink. Only after he sat down with his drink and burger in his hand did he motion to his drink and say, “oh, did you want some of this?”

Through the course of the evening he told me I didn’t know how to correctly take care of my cat, mistook a beautiful abstract painting of a heartbroken woman for Prince (we all know I love Prince – but I still don’t get that), and indicated he expected me to give him a ride home. In retrospect, I wonder if these were all jokes. He couldn’t possibly have been serious.

Giving him the benefit of the doubt, he made a brief reappearance recently. After a couple more dates, it ended after he told me a story (laughing) about his mother abandoning a cat in a parking lot because she thought it was ugly. Now I hate him and his mother.

 

There are a few more to get off my chest that fall in the category of worse.  I’ll save those for round 2.