I may have made a slight mistake the other night when I did something that I would definitely negatively judge someone else, either male or female, for doing. Inadvertently, I may have accidentally opened a conversation, and then flirted with, a good friend of a woman I met, and briefly dated, on JDate. However, I hope that those of you reading this will at least bear with me for the full story before coming to the verdict that I was either in the wrong, or just making an honest mistake.

Recently, I have been trying to be more active on JDate; engaging women by trying to start more IM conversations, and sending out more emails, all in an attempt to try to build up some confidence. The other night I saw a woman online that I thought was cute and, in keeping with my new mentality, I quickly clicked on her name to check out her profile. After a brief skim, I decided to IM her. Since she was wearing an Indiana University shirt in one of her photos, and I attended IU for my undergraduate degree, I thought, “So, are you a fellow IU grad?” was a decent way to open up the conversation.

After a minute or two of no response, I realized that she probably never got my IM because, while I was in the process of looking at her profile, she had gone offline.  Thus, my next move was to send her a flirt and this, once again, led me back to her profile for another in-depth look. Yet, while looking over her profile again and considering what else we might have in common, I began to put the pieces together that I knew this girl better.

23-years-old, special education teacher, Indiana University: I do know this girl. The light bulb illuminated in my head when I suddenly realized that she was a good friend of a woman I had recently dated.

Subsequent to this conclusion were immediate feelings of guilt because I had been trying to flirt with/hit on the friend of someone I had dated. Unfortunately, for me, there was no going back, especially since the IM and flirt had already been sent, and the perceived “damage” had been done. But was this mistake really that big of a deal? Did I really do something so terrible? It’s not like I asked her out on a date, or even kept pursuing her after I realized who she was. Come on. When I break it down in my head it really doesn’t seem that bad: I saw a cute girl online, attempted to flirt with her, realized my connection to her, and now feel silly about it. Sure, judge me if you must. But I’m ready to move on.