Despite the slew of Friendster filly rendezvous, I realize it’s been a while since I’ve been genuinely excited for a date.

Yesterday evening, I staggered drunkenly through two dates, the first a not-really-a-date-but-a-girl-I-knew-and-lost-touch-with-and-met-again-randomly-and-invited-out-for-drinks date, the second a part of the aforementioned (though now mainly repurposed for print) Friendster booty experiment. In short, the results:

The Friendster date was so bad as to be excruciatingly painful; I have now consequently imposed a minimum IQ requirement (and a maximum Gucci limit) on all future booty. [Further details, sadly, must be saved for the actual article.]

The first date (or non-date), however, was absolutely excellent, leaving me wishing it was more of a date date. Though, actually, it may have been more of a date date than I initially realized; at least, that’s what I started to suspect over the course of the evening. Which may have been largely due to the increasing influence of each passing drink. Either way, I was too much of a pansy to push my luck and test that theory. But I’m hoping to drag her out again, at which point, nerves steeled, my luck will definitely be pushed. [Note to the girl, who is doubtless reading this very entry: you have been forewarned.] [Meta-note regarding the previous note: yes, I am aware that using a weblog in this manner is largely akin to the middle school classic “my friend thinks your friend is cute,” about which I am wholly unrepentant. I say: whatever works.]

To extend today’s theme of sappy girl-gift giving tips, another helpful hint for intrepid young daters:

Wrap the gift very well. I repeat, wrap the gift very well. If you cannot, find a store that can (and have them teach you, so you can do it on your own in the future).

Invariably, she would rather receive an empty box exquisitely wrapped than whatever you’ve bought for her in a brown paper bag. (This makes no sense to me either; but it is the way of the world.)

Nota Bene. My online friend Nara Vaughan adds:

Dead right on the gift-wrapping, though it is important to wrap it YOURSELF, not just have the girl at the store do it. (Too professional indicates lack of personal effort.) Tip: Plus points for a small flower/flowers tucked into the ribbon on the top of the present.

On the way to my office this morning, I passed a man buying two dozen roses for his girlfriend’s birthday. I wanted to stop him, to tell him she’d be just as happy to receive a single hand-picked rose as that giant tangled bunch. And what she’d really want, I would have told him, is to receive the other 23 roses, one by one, on days that weren’t birthdays or anniversaries or Hallmark holidays, but where he was just passing by a flower shop and thinking of her.

We guys don’t get it. In our minds, a bigger, more expensive toy is always a better gift than a smaller one. But in the perilous world of girl-gift giving, it really is the thought that counts. Any present that requires effort on our part, demonstrates we were listening that time she hinted at liking something two months back, or just implies that we spend large chunks of the time we’re alone thinking about her, is solid gold.

Is there a statute of limitations on dating friends’ exes? After how many years of post-breakup time does that become kosher? Or is it always tref?

It seems I may have to preemptively curtail my Friendster booty-blogging, as a very major publication (one that really should know better) has asked that I turn such pending exploits into a print feature. If I play my cards right, I just might be able to permanently destroy the entirety of my future love life,

Q. Haven’t you blogged about your love life in the past? Didn’t you stop because it made a horrible mess?
A. Yes. But I’m a glutton for punishment.

Q. What will your mother say when she discovers you’re back to your old hijinks?
A. She will not be pleased. She will not be pleased at all.

Q. Wait. Just a few days ago, you were writing about having a crush on Sarah Brown. Now you’re off chasing other women. What gives?
A. While the crush is still officially on, Que Sera Sera World Headquarters is located in Tulsa, Oklahoma, some fifteen hundred miles away. To paraphrase Ritchie Tenenbaum, “I guess I’ll just have to be secretly in love with her and leave it at that.”

Q. Also, weren’t you pulling together a blog-based dating site? Does this Friendster mission mark the end of that project?
A. No, the blog-based dating site is still very much alive and well. I’ve been making some good progress, though as I have a number of other, more pressing, projects going simultaneously, it may be a couple of months before blogbooty.com (or whatever it will be called; actually, I just made that name up and I kind of like it) hits the web.

Q. You say you’re doing this to prove that straight guys can keep interesting blogs, but ________ is straight and his blog is great.
A. Possible answers include:

1. ________ has simply yet to come to grips with his latent homosexuality.
2. You’re a moron; ________’s site sucks.
3. Good point.

Q. Wait, isn’t self-aggrandizement itself a straight guy’s blog that has existed for years and now draws a fair number of regular readers?
A. Well, actually, yes. On average, about five thousand different people (counted by unique IPs) visit the site each week. Still, over the past year, the amount of drunken mischief chronicled herein has fallen off dramatically, largely due to 1.) being wildly busy with getting Cyan off the ground, and 2.) following that, being in a relationship too good to screw up with stupid blog melodrama. Now that I’m back to bachelorhood, however, I’m hoping these escapades will serve as the kick in the ass I need to lift the site (and my love life) back to its former exploitative glory.

In a nutshell: use Friendster to set up dates with ten different women, court them all in earnest, and blog about the process in gory detail.

Inevitably, about once a month, the mother of any young single guy living in New York asks that her son, as a favor to someone the son doesn’t even really know, meet the unknown person’s daughter for drinks because the girl is moving to New York and doesn’t know anyone there and not that you would end up dating her necessarily but maybe somebody you knew might be interested…

Based upon such ongoing tradition, my friend and colleague Yoav has invented an immensely exciting new game which I will herewith christen “offensive stereotypes and libelous assumptions.”

The basics:

1. Each player puts ten bucks into the pot.

2. All players are seeded with the same basic information about the girl. In the case of the current game:

______ is a mid-twenties Jewish girl living in Chicago. She studied econ at UMIch and currently works in hospital administration. Her mother is heavily involved with Holocaust education.”

3. Based upon this short bio, the players come up collectively with a list of thirty or fourty relevant questions about the girl, then each separately (and based upon their keen instincts and deductive intellects) try to estimate an accurate as possible answer to each question. In this case, questions include (along with, for illustrative purposes, Yoav’s educated estimates):

• Height? 5’3″
• Eye Color? Brown
• Facial Features? Pale, big nose
• Body Type? Zaftig
• Favorite Music? Coldplay, John Mayer
• Sorority? Yes
• Style? Failed overly conservative attempt at NYC hipster
• Corrective Vision? Contacts
• Designer Labels? Yes, but doesn’t flaunt them
• Sports? Soccer until fifth grade
• Degree of Jappiness? 6.5
• On Jdate? Yes, but without a picture
• Tiffanys? Plenty
• Pointy shoes? Not since last year
• Bat Mitzva theme? Luau
• Cool? Edgy? Nope. Nope.
• Plans for future? Nonprofit work “or something artistic”
• etc., etc.

4. When the girl arrives in New York, take her out for drinks, get her absolutely plastered, and have her answer each of the questions herself.

5. Score one point for the player with closest answer on each question.

6. Winner takes all.

7. Losers face eternity of damnation and hellfire for having been wildly amused by this sort of thing, and for being heartless bastards in general. Actually, winner does too.