Dating in the Digital Age

I’ll totally admit that I’m pretty terrible at dating. I like to think I’m pretty good at being a boyfriend, but actually getting there has always been a hard journey for me.

And it’s only gotten harder with technology.

Back in the day (i.e. high school), if I was dating a girl, I usually had to call her. And since I was a geeky, awkward teenager, I hated doing that. I was always afraid that one of the girl’s parents might answer the phone instead, and I’d get grilled about who I was and why I was calling their daughter. This never actually happened, but to my 16 year old mind this was a very real and potentially fatal risk. Thankfully, cellphones started reaching critical mass around this time, so I had less to worry about.

The only exception to this “I had to call her” rule was instant messenging. Yahoo, AIM, and MSN were all pretty popular during my time in high school, so chances were good that I didn’t have to necessarily have to call a girl to talk to her. My crush could be a mere dial-up signal away!

It’s been less than a decade since then, and the entire landscape has changed. The rules are different, and in some cases haven’t even been written yet. For someone who has never been good at playing the dating game, I feel a bit lost at times. I’ve pretty much just resigned myself to making it up as we go along.

For instance, what’s the appropriate policy about “researching” a romantic interest on Facebook? (Don’t give me that look! You all do it!!) How many of their News Feed posts can you like and/or comment on before it’s too much? Or even asking a girl out in a private Facebook message? I did that once and it worked out in my favor, but I doubt it’s something one should make a habit of. Are there exceptions though, such as for someone you met once at a party but aren’t likely to casually run into again?

And then, of course, there’s text messenging. If a girl gives you her number and follows it by saying “text me,” does that mean I shouldn’t call her? And if so, how do I know when it’s okay to start calling the girl?

These are all things that I’ve had to think about since my return to the dating world (yes, my long-time girlfriend B and I have split). As I said earlier, I’m pretty much making things up as I go along, but it’s a brave new world out there. I’d love to hear how others are coping with dating in the digital age.