Even though I thought that my friend’s suggestion that I try to have a “Skype™ Date” was a really good idea considering how much I have been traveling for my job recently, I wasn’t sure that I was going to have the chutzpah to actually ask a women to engage in this type of first date. It’s not that I thought she would laugh in my face at the suggestion and then move on to a similarly good looking nice Jewish guy with a more accommodating 9-5 job, but I just wasn’t sure how any woman would react to the idea of a first date over Skype.

Wednesday night, while we were in Maui preparing to play a game against the University of Hawaii, I suggested to the woman that I had been talking to recently that we try Skype. In spite of the 4-hour time difference, and the fact that neither of us had any idea how to use the program, we were both up for it and decided to give it a shot. We were texting that day and continued our back and forth messaging while we set up separate Skype accounts and I attempted to buy credits so that I could connect with her.

Finally, after a series of trials and errors, I was able to extend an invitation to her and thankfully she accepted (even though it was getting quite late in the central time zone). After Skype finished connecting we were able to see each other “live” for the first time. But even though I could see her lips moving there was no sound coming out on my end. I tried to say something to her and, by using amateur sign language, she was able to tell me that she had no sound on her end either.

After searching through the help section on the Skype website, and trying a few of their troubleshooting suggestions, we decided that our best option was to talk over the phone; at the same time also stay on Skype so that we could see each other. With this solution we essentially created the same experience as if we had actually gotten Skype to work. It did take a few minutes before I adjusted to the fact that I heard what she was saying over the phone before her lips finished moving on the screen.

All in all our first Skype experience wasn’t perfect, but we gave it a try and, more importantly, it did give us the opportunity to at least talk semi-face to face and have a more personal conversation. We ended up talking that night for several hours and really learned a lot about each other, which was really the goal of the whole experiment in the first place. In the end it may not have been the most conventional first date, or one that every woman would have been comfortable with, but it worked for us and I think that’s really cool.