When is the Right Time?

I hate to say it out loud, but I almost miss the simplicity of childhood dating.   Back then, it was a lot easier to know if a girl liked you. Granted, I almost never had a date during high school.  Or college.  But as I get older, it’s just so much harder.   It seems like it should be easier, but it isn’t.

There’s a line in The 40 Year Old Virgin where he says “Maybe it’s too late for me.  Sometimes I think that it is.”  If you’ve ever watched that movie during a dry period (or as I like to call it: life), that line probably struck a chord with you.  It rings true for so many people, particularly when your friends are all dating and getting married and having kids.  You think “Fuck, I’m old.  I am going to die alone.  I’ll probably end up one of those crazy cat people who get a hundred cats and when they die, the cats fucking eat them.”  Granted, that will never happed to me.   I hate cats.   Maybe I’ll build a hamster farm.   And to all my friends who are in love and married out there, I just want to tell you from the bottom of my heart— fuck you.  That’s right, you can kiss my unhappy ass.

Anyway, I’m not here just to tell my friends to eat my ass.  No, this is about talking to women.

I had this woman at my desk this morning. A customer.  Pretty. Not stunning, but cute and sexy.  With freckles.  And almost from the second she opened her mouth, I was a little smitten.  She initiated the conversation.   It started at “the roads in this city are so horrible”, moved on to cars, hybrids and ethanol, conservation… and then took a turn towards politics and immigration and economic depression.  Which is bad.  I don’t know what the rules are when talking to women, but I know you’re not supposed to talk about politics, poverty or your well-reasoned but nearly xenophobic beliefs about immigration and foreign policy… not on a first date, and damn sure not before you’ve gotten a first date.   And the whole time we’re talking, I’m thinking “stop talking!  Change the subject!  Don’t depress the shit out of the pretty girl who is talking to you!!”    Surprisingly, despite the heavy subject matter, it never seemed to affect her.   Which is good.  There was only one question left to me.   When is the right time to a woman out?

Granted, this is a very specific case.  I mean, how do you segue way from “we’re all gonna being living in tents in five years”  to “you wanna get dinner with me some time?” ?     It’s just not a comfortable situation.   But even when you aren’t attempting to give a girl nightmares with your paranoid theories about post apocalyptic futures, it’s awkward.   From the start, it is an impossible predicament.  There’s the initial entrance where you have to come up with something to say to a complete stranger.   People make fun of guys who use cheesy lines, but you know, pick up lines are kind of ingenious in that it gives you something to say, even if it’s moronic. It breaks the ice.   It moves past what you’re unfortunately really thinking.

Hi, I’m Adam.  I don’t know you, but you have got the greatest tits I’ve seen since that trashy barmaid last week.  I’ve got nothing to say to you because we’ve never met and therefore don’t know if we have anything in common or any sort of compatibility vis a vis dating, marriage and rug rats.   That being said, I’d like to get to know you.  Maybe sparks will fly and three weeks from now we’ll be holding hands in front of your friends.  But if not, I’ll settle for fucking your face tonight, drunk or sober; doesn’t matter much to me.

But we can’t really say things like that, because despite their protests to the contrary, women don’t really want anything to do with male honesty.    Yes, even though he may not be considering adultery, he would totally fuck your friends… and your sister… and possibly your Mom.   In fact, it DOES make your ass look big, but that’s okay because he likes your big ass and thoroughly enjoys spanking you while he’s fucking you from behind.    And no, we don’t leave the toilet seat up to annoy you, but we laugh our asses off when you fall in.   Women don’t want to know these things.  But I digress.

Once you manage to think of something to say to her and actually engage a woman in talking, you still have that dilemma.  So when do you ask?   Is it too soon?  Should you ask for her number instead?

I did none of the above.  I wanted too, but I wussed out.  maybe next time.


9 responses to this post.

  1. Posted by Ad Astra on May 12, 2008 at 10:15 pm

    This was hilarious. And unfortunately, the answer is… there is no right time. Not with this one any way. Unless you fit it into that “The conversation is ending, goodbye” phase, then that’s a good way to catch us off guard, and get us to give you our number or whatever you have in mind. We feel pressured, time is of the essence, you’re on the move! So we must react, and we do.

    Cheap trick, but it’s worked on me faster than a rabbit’s hair. Whatever that means…


  2. Huh. To tell you the truth, insecure guys try to avoid doing that last minute “blurt it out” question. It makes you feel like a spaz. And when I picture it in my head, it feel like I’m in the movie Speed and Dennis Hopper is narrating. “Pop Quiz, hot shot. A pretty girl is talking to you. She almost seems interested and your window of opportunity to ask her out is closing in approximately 30 seconds. What do you do? WHAT DO YOU DO?????”

    Try holding a conversation with that shit running through your head. That’ll give you a bowel movement.


  3. WOW. That really was THE FUNNY! -I think Astra’s right… I mean, I definitely see where you’re coming from, but think of it from a slightly different angle. “It’s been great talking with you, I’d like to talk to you more, soooo…” I mean, don’t use that line, just the direction of it. It’s tidy. And it would totally work on me- probably has, I just can’t remember:p


  4. You’re such a tart. Sweet Tart as a matter of fact.


  5. Posted by Loree on May 14, 2008 at 1:26 am

    You crack me up. Now see, with me – that little speech would make me laugh and probably get you laid within the hour, assuming competent delivery. That’s the problem with women – not only do our genitals all work different, but so do our heads.

    But dammit. I can’t believe you didn’t ask her out.


  6. ~I am SO living in the wrong state.

    Eh, she was a customer. If she would have said yes, it would be cool. But if she said no… it could be a problem.


  7. Posted by Becky on June 3, 2008 at 3:17 pm

    I say just suck it up and ask. I am tired of waiting around for guys to pop the question. Worst case scenario, the girl says no and you go home alone, which was the original course of your evening anyway. I consider myself a feminist but I also long for an honest to god old-fashioned gentleman to ask me out, open the car door and say something nice to me once in a while…Wow, that’s been building for a really long time. But honestly, there are very few girls out there that are going to point and laugh and make you feel like an idiot if they don’t want to go out with you. Just ask already!!!!


  8. Very few? Where do you live? I must move to this magical land where women aren’t born evil harpies waiting to emasculate you in front of your friends.

    P.S. You have anger issues. I have a club if you want to join. We have secret handshakes and decoder rings. Sometimes we wrestle.


  9. Posted by Becky on June 3, 2008 at 3:27 pm

    Nebraska, home of the not desperate but also not evil girls.

    As for that club, sign me up! I do love decoder rings!


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