by Douglas Nybacl  

 You got her number, you called her.

Now what do you do?

First dates are a beautiful thing.  They’re a clean slate. If handled correctly you get to be incredibly impressive because every statement is a discovery. 

“New” is a commodity more precious than gold.  Both people are ready and willing to fall because it’s the whole purpose of the exercise.

There’s only one problem.

Chivalry is dying.

Moreover, chivalry is fighting a battle and it’s losing.

The enemy, once again, is The Douchebag.  The Douchebag looks at a first date as a chance to get laid, a Gentleman knows that getting laid on a first date probably isn’t the best sign.  The Douchebag halves the bill or lets her pay, he makes crude jokes, hits on the waitress and thinks a Michael Bay film is smart cinema, but worst of all The Douchebag is unfortunately defining the norm.  

So, once again:  Gentlemen, rise up.

It’s time to take back the first date.  Here’s how  

1. Location:  Pick a place based on your level of interest and previous contact.  Longtime friend?  Someone you met at a party and talked to all night?  Take her to dinner.  Just met her?  Shared witty repartee at a coffee shop?  Eye flirted on the subway?  Take her out for a cocktail.  Drinks can lead to dinner if the date goes well, but if it turns out she owns seventeen cats and calls her mother twelve times during one Lychee Martini that’s going to be a long meal. 

2. Atmosphere: Pick a restaurant or bar that fits your price range but doesn’t look like a ride at Disney Land.  Go somewhere cool, somewhere unique and quiet.  The whole purpose is to get to know each other, which you can’t do if your server is wearing an eye patch and the televisions on the wall are playing re-runs of General Hospital.

3. Manners:  Hold the door for her, when the host/hostess shows you to your table she goes first, you follow to…protect her from bears or something, take her coat and pull her chair out for her.  She orders first always.  Why?  Because she’s prettier, nicer and smells better than you, that’s why.  It takes no effort to do these things, but it makes all the difference.  At the end of the meal, help her into her coat, this gets you close, it’s an intimate gesture that’s both appreciated and combines your personal space bubbles a bit.

4. Conversation:   Charm is confidence.  Don’t feel like you have to spend the entire date smiling.  Take her seriously.  If she’s being funny, laugh, if she’s not, don’t.  Pay close attention to what she has to say, but more importantly what she feels about it.  Believe me, her mind will be the sexiest asset she has and if you remember and reference what she believes in and then build on her ideas you’re in the land where good impressions are truly made.  Be intelligent; don’t try to show her you are.

5. The Bill:  A Gentleman pays.  Pure and simple.  I get fought on this a lot and it’s been a deal breaker for me.  This isn’t a power thing.  You’ve asked her on this date because you like her and you enjoy her company, but more than that, you’ve invited her here because you appreciate her and want to do something nice for her.  A good first date is a gift for both parties, it isn’t about money and it comes with absolutely no strings attached.

6. The Kiss: A first kiss is an amazing thing.  If the date has gone well and you’re both really into each other it’s inevitable.  Be a man.  When the opportunity arises, take it.  You’re not in eighth grade anymore.  Will you be nervous?  Yes.  Do you wait for her to make the first move?  No.  Start gently, if it grows from there, go with it. 

7. Sex:  Don’t.  Trust me.  If the opportunity shows itself, be the guy that politely declines, kisses her thoroughly and leaves.  Call her the next day—do not text her—and when she asks you when you’d like to see her again say, “How about now?”

The first date is an important ritual.  

It exposes the best of us.  You will never have another opportunity to spend time with her without your baggage, in some way, determining your interaction.  With that development comes depth, but for now, for one night, enjoy the shallow waters, they are both the safest and warmest.  They might not last long, but they are amazing while they do.  You have a duty to make it memorable, but more than that to make it romantic.  

Gentlemen, lets make this the new normal.


Previously: The Modern Gentleman: A Gentleman’s Guide to “Picking Up”

Next: The Modern Gentleman: A Gentleman’s Guide to The Next Steps

2 thoughts on “The Modern Gentleman: Gentleman’s Guide to The First Date

  1. Hello Mitchell!

    First of all, thank you for reading and taking the time to comment.

    It sounds like you’re in a bit of a pickle. But fear not, there may be a way around it. When you’re in the position where you’ve developed feelings for a good friend and you’re considering saying something about it, you’re placing yourself and your friendship in a bit of a risky situation. Here’s what I recommend:

    1) Do what you can to figure out if the feeling is mutual. That said, just because she’s being nice to you doesn’t mean she’s “in” to you. I’d try taking her on a hang out that is inherently more romantic, splurge on some tickets to a play, include dinner, make it something you both have to dress up for. The scenario will simply skew the reality of your relationship if only for an evening, into a reality where the idea of “Becoming More” is something that can clearly be entertained by both of you.

    2) If that goes well address it openly and honestly. At the end of the evening, perhaps over cocktails, tell her something to the effect of “This was nice. I think you’re amazing. I’d like to do this again. How about you?” As much as the romantic in me would love to tell you to grab her and kiss her, because she’s one of your best friends take it slow, put the ball in her court and move in baby steps.

    3) If it goes well and she’s into you, DON’T MESS IT UP. Only do this if you are as sure as you can be that you want to be in it for the long haul, otherwise you’re killing a friendship with fire.

    4) If she’s not into it, respect her decision. It won’t be a personal reflection on you, amazing friendships are hard to come by and I’m sure she knows that at well as you, if it doesn’t go the way you want it to you’re still keeping an amazing friend.

    Let me know if you have any more questions! Thank you for reading, keep on sharing and spreading the word.



  2. Douglas this is just what I needed to read – you said at the start of this article in point number one – Location – Life long friend?

    I have this friend and she is amazing – at first I didn’t have any initial feelings for her but she is extremely attractive. Over the course of a year our friendship has become very strong – just recently however I have developed feeling for this girl.

    You have another post about nice guy vs good guy – Reading that I am clearly the good guy because I invest in our conversations and that is why we get so much value out of our friendship.

    But how does one go about asking a long time friend out on a first day with the intention of her knowing that it is a date, not just another catch up?

    By the way point number 4 was one of my favourites.

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