IJMM Strike One, and Some Dating Tips for Men

Posted on November 30, 2010


The million dollar date has been had, and lo, it hath failed.

As I said on Twitter: To recap, I didn’t like him but I’m kind of annoyed that he didn’t like me. I did wear a piece of arugula on my boob for part of the date, until he pointed it out, so maybe that did it.

In my defense, he wore a Hawaiian shirt and sneakers and liked NASCAR.  Which, I know!  So do lots of perfectly nice people. Who I do not want to see naked. Ever.

We had plenty to talk about and some common interests, and he’s a nice guy.  But there was definitely no ‘there” there…we parted with a handshake, and even that felt a little too intimate.

Anyway, not much more to say than that.  On to the next one.  But before I go, I have two very important pieces of dating advice for men to bestow in honor of this failed date and failed dates everywhere.  If I can reach ONE man with these messages, I will have far exceeded my potential to make lasting change in this world.

Dating Tips for Men on a First Date

1.  If you are meeting a woman at an upscale bar/restaurant in the evening, don’t wear jeans unless they are damn sexy jeans and you are supermodel-confident that you can rock them with elan. There are men out there who can, but not many, and odds are that if you don’t KNOW beyond a shadow of a doubt that you are one of them, you’re not.

Am I a fashionista?  Oh no, my friends.  Far from it.  Did I wear a cute and well-chosen dress with appropriate accessories and hot boots?  You bet your sweet ass I did.  My cleavage was set off wonderfully by the sprightly green of the arugula that was lodged there for an hour, too.

2.  For the love of Jesus and Buddha and your childhood teddy bear and everything holy, ASK HER SOME FUCKING QUESTIONS already.

Oh my God, how long can you possibly go on talking about yourself without ever asking your date anything?  Why are you giving pedantic, multi-page answers to questions and not ever making a single inquiry?  How do you get by in life with such appalling social skills?


Girl: So, you like to travel?  Where’s the last fun place you went?

Boy: probably Italy…we went here and here and here and here, and it took this long to get there on the train, and I ate this and this and this.  And then I did this, and this, but none of it was funny–I’m just basically reciting the minutia of our itinerary.  And oh, you should see this someday, or go here, and if you do, be sure to say “grazie”–that means thank you.  Also, gelato is delicious. Nothing specific to say about it, just that I liked it.  Random comment about Americans being stupid travelers.  Random comment about not being that impressed by the sophistication level of Europeans. Also, they smell.  Now I’m going to list some more places I went.  Now I’m done.

Expectant pause.

Girl: (Surely this is where he’s going to ask me where I went on my last fun trip? Or if I’ve ever been to Italy?)

More pause. Pause grows uncomfortable.

Girl: Wow, it sounds like you had a great time.

Boy: I did.  And I also had a great time once in Spain. If you ever go…

Girl: Actually, I was there last year for a month.

Boy: Huh. Well if you ever get to Majorca….

See what went wrong there?

Just ask yourself:  Am I asking roughly as many questions as I’m answering?  She knows where I’m from–did I ask where she’s from?  I told her my entire job history–do I know what kind of work she does?  She now knows my mother’s primary care physician’s pager number–did I ask her how her day was?

If the answer to the above questions is “no”, YOU ARE DOING IT WRONG.

The exact same principles apply to pre-meeting emails–are you asking questions?  When she asks, So what brought you to DC?, the proper response is XYZ brought me to DC, and I am happy/sad/enraged about it xx years later.  Here is a brief humorous anecdote to illustrate my point. What about you?

See those three words at the end, and that adorable little squiggly punctuation mark after them?  Put some of those in your emails.  Evincing some curiosity what a woman has to say is not only in accordance with basic laws of civility and a validation of the social construct and just plain good manners, it’s also a total panty dropper.

Or maybe you’ll find out those panties need to stay on.  For all you know, her answer to the bolded question above might be A desire to wreak cyberterror on the US government or I thought Sarah Palin was going to be VP and I was hoping to seduce her because I think she’s the smartest and most beautiful person in the world.

But you will never know if you don’t ask some questions.  You’ll thank me later for this.  Spread the word.