Recently, I was having a very nice email conversation with a woman that I had met on JDate. We had sent emails back and forth expressing some of the things going on in our lives, some information about our jobs and interests as well as other random factoids which gave the other person a glimpse into our everyday lives and personalities. In fact, our interaction was going so well that after sending my third email I decided in the next I would ask her out on a date, assuming I got the vibe that she was still interested.

However, before I proceed with my story, I need to give a little bit of background on my third email. In the opening paragraph, in response to her telling me about a job she had just gotten working with special needs children, I commented, “One of my best friends is a teacher’s aide for special needs children at a school in the north suburbs and she loves it.” I then went on to ask some questions, including if she had anything exciting planned for the upcoming weekend.

With the sending of this email I had the utmost confidence that the conversation was going to continue, and that I hadn’t said anything controversial which might derail my chances of getting a date. Unfortunately, what I failed to consider was that I had casually brought up, without any context or previous mentioning, that one of my best friends was a woman. Therefore, when she responded to my third email with her opinion that men and women couldn’t be close friends, I was quite confused by what had prompted her to express such strong opinions on the subject.

While I understood her perspective that it is sometimes difficult for men and women to be close friends (due to a perceived, and sometimes real, underlying sexual tension between them), I felt like it was unfair for her to make that assumption with me. Furthermore, even though I did feel badly about the way she reacted, it was good that she expressed her opinion; had we started dating, this would definitely have been a point of contention later on since I have many close female friends.

In the end, my casual reference to a close female friend raised a red flag in her mind the same way that her reaction to it did for me. That’s why, ultimately, I realized that it’s better to go with the normal flow of conversation; don’t over think or script the perfect things to say to someone you are just getting to know.  I have many close female friends that I have no interest in dating, and have zero interest in dating me. This being said, however, I still think I’m better off putting the information out there, and letting the women I talk to decide for themselves. After all, everything comes out eventually.