A Challenge

My friend Pen threw down the gauntlet today. I have been challenged to a battle of wills (because somehow a battle of apathy seems impossible). This is her contention: I will not find a date in the calendar year 2009. She thinks I’ve allowed myself to become distracted by work, more work and fantasy men in order to avoid (or sublimate) my natural instinct to “couple”.

Now before any of you jump to my defense (no, really, you should have, but that’s fine… I’m not hurt), she means well. She just knows that my propensity for alone outweighs any desire to socialize with other human beings (outside of a laminated list I keep on hand for emergencies). And the bet wasn’t so much that I couldn’t possibly find a guy in Los Angeles to go out with me (although that’s a genuine concern), but that I would not be taking any remarkable steps to make that happen.

So, she has decided to speak in a language that I understand: the language of cash. She has bet me $100 that I will not go out on a date in 2009.

Naturally, my first instinct is to say, “Eh, whatever” and then grab another muffin from the cart. Also, I’m a little concerned that if she’s technically paying me to date that somehow prostitution fits into this scenario. The old moral compass can’t quite embrace that element. And the life of hermit doesn’t really lend itself to bar hopping.

But I’m very competitive, and I like money.

What to do ….

Being highly analytical, I weighed my options and figured I could find a loophole. Surely a male friend could by me a drink (that I would nurse for a couple of hours without drinking, of course), and I could come away with a new shoe fund.

Sadly, Pen was ahead of me on this one. She had a list of criteria:

  • Single, straight, male (although separated male is also acceptable);
  • I must have some romantic interest in him, and (this is the tricky part) he has to have some romantic interest in me (unless this is a set-up and then how the heck would I know this);
  • I have to find him attractive (although, again, if this is a set-up, it’s not my fault if the spark isn’t there);
  • He has to take me out to an event (ie can’t be fixing the plumbing in my apartment when I get home);
  • We can’t split the tab (I tried to argue this point, but we’re on wait and see with this one);
  • He must be over 18 (can’t take the nephews bowling, apparently); and
  • I must have an impure thought during the course of the date (thankfully, she didn’t specify if the impure thought had to be about the date, or cursing her for getting me into this).

So, here we are. The bet has been made. Now the questions is will I win the bet, win the bet by getting around the rules, or fail miserably, thus allowing Pen to keep the money?

Did I mention that I really like winning even if I don’t necessarily want the thing I’ve won?

This could get interesting.


My friend DM just jumped in with another of $100. That’s $200 to me if I go out on a date following that criteria by Dec. 31, 2009. She’s actually willing to extend it to Jan. 2. She’s willing to throw in an extra $50 to kiss him on New Year’s Eve.


And my friend Bonnie is in for another $10.


Mich just added $50. We’re up to $260.

You realize I’m going to go out on a date just to spite you people, right. 😉 Get those checkbooks out.

4 comments on “A Challenge”

  1. danielletbd

    I'm intrigued that you agreed to these terms. I'm also intrigued that they are not giving you a year deadline but rather having the deadline be WITHIN the calendar year, which really gives you less than six months.PS Do you even want to go on a date? Because if not, going on a random date with a random dude is only going to make things worse. Then again, it is free money if you follow through even if you don't want to. Right now, extra cash is a nice incentive. Want me to pretend to be you on the date and we split the profits? 🙂

  2. Marisa

    Very interesting. Love that your desire to win isn't so much to go on the date, or even to get the money, but it's the fact that you WANT TO WIN.Keep us updated on your quest!

  3. Kate, Dating in LA

    LOL!! I love how you guys are completely willing to help me get around the rules. But no, I will not resort to subterfuge… immediately. That wont come until December when I'm in danger of losing the bet.Also, I think they should pay me double if the guy on the date with me is Clooney.

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