A few years ago, when I was still online dating, I came across the profile of a cute Latino. His profile indicated that he lived near me and that he, like myself, enjoyed running. Once we started talking the conversation flowed like water. We spoke, consistently, for a few weeks before we decided to meet up. All seemed to be going well, but he kept giving me random reasons why he couldn’t meet me when it was convenient for me. He kept trying to get me to meet him at his house or in front of his building late at night. I made it clear to him that, if he wanted to meet me, he would have to do so at my convenience. Even though he was resistant to meeting, we continued to communicate.
During one of our conversations, I asked him what he did for work. He told that he was a personal assistant for his cousin (whom he claimed was Jessica Caban, the longtime girlfriend of Bruno Mars). He also said that he was a part-time hairstylist. I made a comment, that I thought would end up being a light-hearted joke. In response to him saying that he was a hairstylist, I joked, and asked if he was also gay. I expected a variety of responses, equating to a no. Although he did say no, when he told me that he was a cross-dresser, I almost choked. Immediately my phone was flooded with messages from him dressed like a woman. Now, don’t get me wrong, he didn’t look half-bad; I simply wasn’t expecting that. I thought about deleting his number and blocking him, but I wondered if I was being too close-minded. There was a party of me that knew I couldn’t get with it. But there was another part of me that considered the courage that it took for him to be honest with me; and, that part didn’t want to just walk away.
We agreed to meet up one evening and go for a walk in Central Park. He was less handsome in person, but still good looking. I don’t remember what I wore; but I remember he wore a huge multi-colored puffer jacket and NYC Marathon ASICS. —Why do I remember those details, you ask. The only reason why I remember them is because he kept mentioning them. He kept mentioning how expensive his coat and sneakers were, and how much money he had. As he tried to win me over by saying how much money he had, I kept changing the conversation to other topics. We spoke about running, him doing hair, and eventually I asked him when he started cross-dressing. He explained that on one day he just decided to try it and he liked it. He had this cockiness about him that I hated; but his honesty kept me intrigued.
I felt like dessert, so we walked down to Pinkberry. On our walk, the conversation continued to evolve. I was semi-surprised to think that despite how things began; we were actually having a decent first date. Once inside of Pinkberry, and only because he made such a big deal on how much money he had, I was taken aback when he didn’t offer to pay for my $7 dollar dessert. —If you’ve been following my blog from the beginning, you know how I feel about men that don’t offer to pay on first dates. If a man doesn’t pay on a first date, there will not be a second. I thought to myself, for a guy donning $130+ sneakers, and a coat that he claimed was over $500, the least he could do was buy my frozen yogurt; when he did not, it was an automatic major deduction. I was ready do ditch his ass; but, unfortunately, he lived in my area, and we had to walk in the same direction. He said that he was thirsty; so, walking back uptown, we stopped into Whole Foods. He walked to the beverage station, grabbed a beverage, and asked me if I wanted anything. I said no, and I started walking towards the cash register. I was, once again, taken aback when he turned around and made his way back to the entrance. —Yes! While wearing over $600, this fool decided to steal a seltzer water from Whole Foods. I looked at him like he was bat-shit crazy. Once outside of the store I ripped into him about what he did, and he seemed to not care. I needed to change the conversation over the remaining 15 blocks, so we spoke about movies and TV shows. When he reached his building, he invited me to come up, but I eagerly declined and made my way home.
Most women would’ve blocked his number. However, there is always (and probably will forever) be a part of me that never knows when to call it quits. I can say it in my mind, but there is always the heart. When the mind and heart align, then along comes the conscience, that convinces me to give a person one more chance. So, after our first meet & greet, where he stole and didn’t even buy me a dessert, we were still talking. A part of me found it interesting having a person that was so different in my life. So, I wasn’t quite ready to sever all ties. A week later, I was with my friends at the bar having wings, and my date came up. I went over all the details of the date and they were appalled for me. When I mentioned that he was also a cross-dresser, they thought that I was out of my mind for going on the date, in the first place. I tried to justify the reasons for us staying in contact, but in the end, I knew it had run its course.
After a few nights, he went from being interesting and different to classic fuck-boy. One evening, he kept repeatedly asking me to come over and I told him no. He then proceeded to say that if I didn’t come over, he would call someone else to. I guess he thought my decision to talk to him was out of desperation, but I was simply trying to be open-minded. I told him he was well within his right to do what he wanted. This went on for about twenty more minutes. Growing annoyed, I told him that I would block him. When he didn’t stop, I did just that. To this day, I still wonder why I even went down that road in the first place. I knew, the moment he told me that he cross-dressed, red flags went up. After his behavior on the first date, I knew there would be no romantic future. I don’t really know what it was, but I wanted to give him a chance to see if we could at least be friends. In the end, nobody can say I didn’t try.