Old School for the New School Timeless Dating Advice: How to Ask a Girl Out

Some dating advice is just terrible. Most of it, actually. In dating as in other areas of life, the classics never go out of style…here are some pointers to help you out.

Stamps. Frigging stamps — the lack thereof — is what has finality pissed me off enough to write about some of the most fundamental differences about being a guy in today’s digital world as compared to the pre-Internet analog world. I just walked several blocks in midtown Manhattan looking for stamps. Nobody’s selling stamps, not even where they usually do. And, as much as I need the exercise, the nearest Post Office is too far away on a day so cold.

In the pre-Internet world, I’d have stamps by now — as many as I wanted too! Because you used to send stuff by mail “back in the day”. 
Things in the analog world sure were different. And I don’t just mean the analog world in general. Everybody over a certain age surely has a lot to say about how digital technology changed things generally. No, I am talking about something far more specific that’s gone forever: the analog world of pre-AIDS, pre-social media New York City.

THAT New York City was a paradise for guys of a certain age. THAT NYC challenged a man. Not like today — swipe this photo, text that gal, join some dating site. A lot of the early-stage friction has been removed from how a guy goes about first meeting a girl. Friction was good — it toughened a guy. It is so so easy now to get that first meeting with a girl that it is contributing mightily to the pussification of America.

America was a world power back in analog, pre-AIDS NYC, when young men of drinking age had to figure out how to con their ways past hulking doormen guarding the entrances to clubs that would be “over” in a matter of months. America was a world power when those same men had to overpay for drinks (or be thrown out), and then had to assess just how much they could safely drink before the odds of getting off a smart introductory line to an unknown lady would approach zero percent. America was a world power when its men in cities like mine were meeting girls in bars about whom they knew absolutely nothing — but being brave lads, they fought the hard battles to take those girls home, and as soon as possible after that first encounter. (Hopefully, one of your more sober friends would remember her name when you showed up with her at brunch the next morning.)

America today is a waning power in this increasingly dangerous world. Coincidence? I think not.

Nowadays, if a guy screws up big-time in how he treats a woman, he risks his ill behavior being broadcast to the world. THE WORLD. In our day, you worried only that you’d never date any of that woman’s closest friends — except, of course, for the disloyal, catty ones who were only pretending to be her friends. There were always more of them around than you’d have predicted growing up. Because girls are just not as loyal to their friends as men are, where dating is concerned. But I digress …

Every mistake made today — every ill-advised photo, every stupid remark that gets quoted, Tweeted, re-Tweeted and worse — puts a guy at risk of public humiliation, or of losing a job offer or some other future opportunity. All because there is no longer any true privacy. As a result, far too many of today’s young men cower in fear. They are addicted to the very same digital technologies that guarantee their downfall, should they mess up.

Put away your damn phones, and have a drink or two, and go meet a girl the old-fashioned way for God’s sake! But after you meet her, remember — however much bolder you’ve become, you’re still just a guy. A guy who, if he has one drink too many, will almost certainly say something incredibly wrong or stupid or too aggressive — undermining all the great groundwork you did in the prior X minutes. Get her contact information, and quickly — and then, if she’s not screaming “Take me home, I love you!” — well, get the hell out of wherever you are while the going’s good, so that she’ll actually agree to see you in the cold, harsh light of day.

That’s actually how I met my wife … Best of luck

-Cold Beer & Broads

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