The Filibuster: A Man’s Guide to a First Date

I recently sent Jenn a link to another beauty blog that had a list of looks men don’t like on a woman.  Her response was “Seeing as I’ve done most of those looks, it’s no wonder I’m single. I guess I require a man who has taste.”

It got me thinking about how to identify a man with taste and class – what would our first date look like?  Here’s some advice for the men out there.


  1. Bring me flowers on the first date. Are we going to prom?  No?  Okay then, save your money.

Wendy wearing a corsage at prom

I’m NOT saying don’t be thoughtful.  A rose (or God-forbid a dozen) means something when you’ve been dating for a long time and/or it’s a special occasion, but flowers on the first date can convey something entirely different:

First Date Flowers Decoded

  1. Curse.  Don’t get me wrong, anyone who knows me knows I can cuss a blue streak.  But that’s the point: YOU don’t know me, not yet.  If you don’t have enough class to watch your mouth on our first date how can I expect you to not drop the F-bomb if you’re ever lucky enough to meet my grandmother?
  1. Make sexual innuendo.  This is a fine line, because I sometimes find juvenile sex jokes funny and disarming.  If we just saw a Will Farrell movie it’s practically unavoidable.  I think the important factors in non-offensive use of sex jokes on a date are:
    • You don’t imply you and I will be having sex
    • If you do make reference to us having sex, it’s in a completely self-depreciating way [My ex managed to work in that he was hung like a mosquito, which cracked me up.  Mostly because I assumed it wasn’t true.]
    • It must not be mean-spirited towards someone else
    • It shouldn’t be too graphic.  As in pornographic.

This is best left to the professionals, so if you aren’t confident you can walk that line don’t try it.

  1. Be early.  I’m glad you’re so excited for your date that you left your house early anticipating traffic/getting lost/being kidnapped by a cult and spending years trying to escape.  But I’m still trying to look good for said date, and now I feel rushed.

Notice I don’t tell you not to be late.  Late can work in your favor but requires careful application.  Here is my super-scientific Lateness Scale for your dating convenience:

Super-scientific Lateness Scale

  1. Try to kiss me on the lips.  This is another tricky judgment call.  If we’ve been friends for a while and we suddenly find ourselves on a mutually-designated date then it’s probably okay.  Scratch that, it’s probably a good idea unless you want to go back to the friend zone.  But if we’ve never met face-to-face before or only a few times, kiss me on the cheek.  Make it clear you’re interested in seeing me again, but leave me curious.


  1. Tell me I look great.  “Stunning” is an under-utilized word. – use it.

A corollary to this: one compliment is sweet, two is flattering, but any more and I’ll start to feel like a piece of meat OR that you’re dating way above your caste.  Which means I’m dating way below….  Plus it indirectly insults every other woman you’ve dated, and hey, that could be me!

Corollary to the corollary: this “two max” rule does not apply to compliments unrelated to physical attributes.  In fact, the more often you tell me that I’m smart or funny the more likely I am to believe you mean it.

  1. Demonstrate good manners. Say please and thank you, open doors, and be unnecessarily gracious to everyone.
  1. Tip the wait-staff a little more than you need to.  This assumes the service was decent.  A person who is unkind to wait-staff is a small and miserable individual.
  1. Give me your full attention.  Make me feel like there’s no place else you’d rather be than with me.  Don’t text (period) and don’t take phone calls unless you’re actually on-call for your job.  Keep your eyes on me unless I point out some girl experiencing imminent wardrobe malfunction: then you can stare to demonstrate that you’re listening to me.  Everybody wins!
  1. Make me laugh.  You can never, ever go wrong here.

Of course the most important DO is to be yourself.  Maybe you aren’t the coolest guy, the richest guy, the smoothest guy – there’s someone out there for everyone, and if you’re being someone you’re not you’re wasting precious time for both of us!

What’s your dating advice for the men out there? 

Tell us about a really great first date or a really awful one!

Photos and images author’s own.

3 thoughts on “The Filibuster: A Man’s Guide to a First Date

  1. jenn

    DO leave your phone in the car. Nothing turns me off more than a guy checking his phone in front of me. In fact, no phone on date = VERY hot.

  2. Erika

    I disagree about the flowers! I love to get flowers, and I think someone who gets flowers for a first date has some serious balls. Agreed about the phone although I have actually been married long enough that the phone was not an issue when I was dating!! I mean, there were cell phones but I’m pretty sure texting wasn’t around yet and people weren’t as tethered to them as they are now.

    I totally agree about the compliments, especially being complimented for brains.

    I would list my bad dates here but it would be too appalling.

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