Guy's Guy™

The Guys’ Guy’s Guide to Online Dating (Part 1)


When I was in my twenties, I met women the old fashioned way. This was before the age of ubiquitous cell phones, female wingmen, and dating apps. In the old days, drumming up the nerve to approach a woman took courage.

Like a lot of young men I wasn’t always comfortable in my own skin.  If I saw a lady who appealed to me, I’d drum up the courage to greet her with a friendly hello. Then, hopefully, I’d come up with something to say, an interesting question, or anything to keep things going. It was a challenge, but over time, I developed a decent rap. Sometimes I’d lose my nerve and stand at the bar too long nursing my Amstel Light. So, I’d lose out to some other guy who’d beat me to the punch. I met a lot of women and sure, I got shot down plenty of times too, but it was all part of putting myself on the front lines.

In many ways, meeting women the old fashioned way was a lot like sales. To succeed you needed to know who you were and what you had to offer. You had to qualify your prospect quickly so you wouldn’t waste time with someone who was married or in a committed relationship. Most importantly, you needed to know how to strike up a conversation and close the deal. So, I learned how to ask the right kind of questions, and stay positive in the face of rejection, and how to overcome obstacles to make a connection. Over time, I became fearless and experienced a lot of success. I met women in bars, gyms, laundry mats, libraries, bookstores, buses, airplanes, or just about anywhere. And, beyond ‘winning’ at the mating game, meeting women was fun.

But the times have changed. Technology has now made men lazy. These days, a guy can score dates with smart, successful, attractive women while sitting at home in his tighty-whiteys by just plinking on his laptop. All of the apps and websites have made it very convenient for men to meet women. You could say that technology has made dating much, much easier. But, hold on. From what I can tell, technology can only take you so far. Whether you are a man or woman, to make a real connection with a member of the opposite sex you still need self-confidence, conversational skills, a sense of humor, and a dash of self-deprecation.

There’s still a lot to be said from those days when a man had to learn how to approach a woman, face-to-face, literally on the front lines. Men used to study ‘pick-up’ lines and share the best ones with their pals. It took a lot of nerve to step up to the plate and simply be you.

Here is a scenario of how things might have played out back in the day. A guy walks into a bar.He scans the room and takes the seat next to a pretty woman sitting alone nursing a glass of wine. He settles in and orders a beer. Out of the corner of his eye he casually checks out the woman seated next to him. Sensing his gaze, she takes out a cigarette. He strikes a match and holds it out for her. She exhales smoke, smiles and thanks him. “Hi, I’m Lou,” he says. “Cindy,” she responds. From here, anything could happen. That’s how lots of guys met women before technology took over our lives and smoking was banned in bars.

If that scene were replayed today, the woman at the bar would probably be on her phone texting or checking emails. She might not notice the guy sitting next to her and he might not even look up from his phone to notice her. The guy would probably order a beer, place his phone on the bar and stare up at the bar’s two-dozen giant television screens. Between sips of beer, he’d check his phone. Maybe he’d check his online dating app to see if anyone in the bar was on the same service. Then, when his friends would show up, all the guys would stand around drinking, watching the games and discussing their fantasy sports teams. Meanwhile, the attractive woman seated next to them, would greet her cute friend’s arrival and the ladies would probably chat over a drink before moving to a table to discuss their jobs and talk about why there are no good men around.

While technology has made things really convenient in a lot of ways, the problem is that people, today, are distracted by waves of ubiquitous media. Most people have trouble being present in the world directly around them and this makes it hard for them to connect. These days, when young people go out, an impenetrable wall of phones, apps, emails, texts, TV’s and a closed circle of friends usually surround them. In most cases, they don’t organically engage with new people. This brings along a new set of challenges to dating in today’s tech-driven culture. It seems that to succeed in today’s fast-paced scene, you need a blend of digital dexterity and that, all-important, old school charm. The digital portion of the equation is relatively easy to pick up. But knowing how to strike up a good conversation and converse with confidence and finesse takes time. But it’s worth it. In this area, daters over forty a big advantage over younger daters who rely too heavily on their cell phones, iPads, and laptops to communicate.

The trick is to learn your way around today’s digital dating landscape while deploying your old school charm. If you want to succeed, you need to stay up-to-date on the multitude of digital dating tools and apps. It’s critical that you learn how to communicate quickly and effectively through your digital device. His will get you half way to the finish line. I’ve learned that to win, you still need to be fluent in the art of conversation and flirtation. That can only take place in person. After all, no matter how much game and witty repartee you may demonstrate in your texts or emails, eventually you’ll find yourself face to face with the object of your desire. That’s the only place where real chemistry can happen.  

To be continued…