by Douglas Nyback  

We live for romance.  We live for the moments that take our breath away. We live amidst thousands of people that flit in and out of our day to day lives, one at a time. But there is always that one person who catches our eye and, even if only for a moment, takes our breath away.  

Whether it’s at a bar, on the street, across a crowded room or on the subway, that moment is epic, that moment, is a miracle. The question is, how do you turn that one epic moment into a date?

This is where the ‘picking up’ happens. Or is at least considered.

But here’s the thing: This isn’t an apple harvest. A gentleman doesn’t ‘pick up’, he leaves an impression. We’re throwing out the term ‘picking up’. We’re putting it down.

“I want to ask her out, but I don’t know how” – I hear this all the time and that’s the big question: how do you?

The key is courage.  Seriously, man up. We all remember the feeling of asking someone out in Junior High or High School and getting turned down.  Remember  that moment in the movie theatre when you’re not sure if it’s really a date and you spend half of the show building up the courage to hold her hand?  Here’s the thing: that feeling of uncertainty, it never goes away.  It’s never easy to ask someone out, even if you know beyond a shadow of a doubt that they’re interested.  You’ll be scared.  Deal with it.  Men stormed the beaches of Normandy so try to get past how her perfume is making you forget your own name.

Some general guidelines to follow:

1. When you’re in the ‘star crossed moment’ have the courage to hold onto the gaze just a bit longer.  It’ll feel like an eternity, but I promise you, it’ll only be couple of seconds.  Measure these seconds by breath, not by counting.  Flirtation begins with thought process, there’s nothing more interesting than the distance between two people as they try to figure each other out.

2. Pickup Lines are dead.  The Douchebag might argue but consider this article a shotgun blast to the collective Pickup Line’s face.  Gone are the days of, “Did it hurt…when you fell from heaven?”  or “I’d love to make you breakfast in the morning.” I’ve seen some utterly ridiculous tactics of introducing oneself to a woman, but truthfully, the only one I can officially endorse is “Hi.”

3. It’s romantic.  Unless you’re looking to ask the girl across the bar from you to be your accountant, embrace the poetry of the moment.  You don’t have to be Shakespeare to sweep someone off their feet, but you do have to try.  You’re approaching her because you like something about her.  Do her eyes make you utterly incapable of conscious thought?  Tell her that.   Can’t get over how her laugh is the most genuine thing you’ve ever heard?  Let her know. Don’t embellish, speak the truth.  If you feel like a total idiot, commit.  Charm isn’t being James Bond, it’s being yourself.  Why start a potentially good thing with an embellishment?

4. If you’re at a bar, discreetly ask the bartender to put her next round on you.  PLEASE NOTE:  She doesn’t owe you anything for this.  If she chooses not to instantly fall head over heels for you, deal with it, a martini isn’t a proposal on top of the Eifel Tower; it’s a martini.  If she does acknowledge it, head over confidently, be courteous and get to know her.  

5. When the time is right, man up and ask for a number. Not any number, her number. There comes a point in every exchange where it stops being a conversation and either gets awkward or starts to become a date.  You don’t want your first impression to be your first date, so know when to head back to where your friends are, or back to whatever it was that you were doing.  If she doesn’t give you her number it’s not because she’s a terrible person, it’s because she’s not into you. Trust me, if she’s legitimately not interested there’s no point in continuing your pursuit. You can’t force romance.  

6. Once (if) you’ve gotten her number don’t wait six days to call her.  Anyone telling you that is an overgrown frat boy.  If you like her, call her.  She’s lovely and you’ll get to see her faster which will make you happy.  That’s science.  (NOTE:  A Gentleman doesn’t arrange a first date over text or Facebook.  Arranging a date over Facebook makes you look exactly as lame as you feel).  

The most important thing to remember is that even if you are well dressed, properly fit and confident it’s never easy, but fortune favors the brave.  

A Gentleman doesn’t need his buddy to talk him up, nor does he need to lie, embellish, boast or try to buy lady’s affection.  He may, however, require a quick hit of courage.  I recommend Macallan 12 with just a dash of water, won’t break the bank, cures what ails you and doesn’t make you smell like a distillery.

Previously: The Modern Gentleman: Style Guide

Next: The Modern Gentleman: Gentleman’s Guide to First Date

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