Archives by Year: 2008 // 2009 // 2010 // 2011 // 2012 // 2013 // 2014 // 2015 // 2016 // 2017 // 2018


The Headless Horseman

You may not have noticed, but I only blog about dates with guys I know I’ll NEVER see again.


Well, I think it has a little something to do with the notion that a guy I’m actually interested in may not be too keen on the idea of me broadcasting my opinions about him on the Internet. I mean, do you really want to read a review of yourself? On a first date??? I know I don’t.

That’s almost as much of a buzzkill as telling these guys the name of the website I work for (hint: it has to do with weddings). Based on the general reaction so far, it would be less disturbing to say I work in a leper colony.

Anyway, I held off for 2 months on writing about the guy I call The Headless Horseman. I thought we might meet up again. Mainly, because he said, “Let’s meet up again!” But that ship has sailed… so away we go!

He was from Chemistry. He was 37, lived in CT, never married, no kids, no pets. Had an MBA, worked in finance (Again? Really? Seriously? I need to diversify my portfolio. Then again, maybe I don't.). He claimed to be 6’2”, with brown eyes and brown hair. I say “claimed,” because he didn’t have any photos posted. Not a one.

Now, I KNOW what you’re thinking. No photo? Are you CRAZY? He must be married, or horribly disfigured, or 1 of the 10 Most Wanted. I should really know better.

It’s true. He might have been all those things, but I plowed ahead anyway. SO unlike me.

We emailed pretty regularly for a few weeks. ONLY email -- he never gave me a phone number, and never asked for mine. And while there was a definite formula to his responses -- roughly 4 paragraphs long, with exactly 2 questions every time -- the substance of his emails was both nice and normal. The only oddball thing was that he still would NOT give up the photo, even after I explicitly asked for it! It was too personal, he said. Okaaaay.

Eventually, he did ask me out. I secretly wondered if he'd be wearing a bag over his very private head. When I met him, I didn’t even know who I was looking for. Not smart, I know. But could I really get killed at a Starbucks in the Waldorf? I’m thinking no...

And, turns out he WAS normal looking. Totally, average-ly, middle of the road-ly, normal looking. Forgettable, even. Like a piece of dry toast. I was like, what, no tan line from where his wedding band usually is? No droopy eye so I can’t tell if it’s staring at me or my boob? No giant scorpion tattoo on his face from his stint in the Joint?

Nope. Nada. Normal.

We spent about an hour and a half talking -- conversation was easy breezy. I even laughed. On purpose! And for the first time during this whole miserable online dating process, I thought, here’s someone who’s NOT horrible! I just might like to see this not horrible person again!

When we parted ways, he shook my hand to say goodbye (karma for Costanza?), which I didn’t take as a good sign. But he emailed me a few days later saying he had a nice time and wanted to do it again. Which I DID take as a good sign. Over the next 6 weeks, though, The Headless Horseman drifted from potential to pen pal to poltergeist.

As you know, I’m not terribly forward, so I waited for him to make our next date. We emailed back and forth for about two weeks, but not a peep. And these weren’t dead-end emails where he was just too nice to come out and say he wasn’t interested. He always asked me MORE questions. So I answered them. Until I got fed up with being pen pals.

I decided to be bold.

I told him I’d be in CT visiting my brother and sister-in-law before their baby was born and it would be great to meet up for lunch on my way back to the city. Lunch on a Sunday. Sounds casual enough, right? Non-scary? He responded about an hour later saying he’d “very much look forward to meeting” but he was golfing with his old boss. Ok, that’s cool. He said he expected to be back in the city in the next 2 weeks for work and would let me know once he knew the exact date.

Well I certainly wasn’t putting another date out there. So I waited. He kept emailing, so I replied. And then waited some more. Tenth email’s the charm, right? Wrong.

After that, he disappeared. Poof, like a ghost. Until this past Friday.

Pumpkin Head popped up out of the blue. Right there in my inbox! He changed his email formula too. Two paragraphs, NO questions...

Work’s been crazy, he said. I’m sorry, he said. Hasn’t had time for dating, which was the “story of his life.” Blah blah blah. Whatevs. I didn’t want to be totally rude so I sent him a short note today (5 days later) to wish him the best, and say I hope he makes time to enjoy the summer (if the sun ever comes out again). The end.

And so, here we are. What do YOU think happened here?

Was his job REALLY such a drag? Or was he just not that into me? I’m thinking the latter… which is ok by me. Because at the end of the day, I want a guy with a head. And some balls.


Anonymous said...

"I secretly wondered if he'd be wearing a bag over his very private head."

I'm still laughing about that...

the executive's wife said...

You don't want a guy who's going to put his work ahead of getting to know you at this stage. Or else there's no help for you down the line when he brings his Blackberry on your honeymoon.

Or was that just my husband??

Anonymous said...

He's obviously not ready to even entertain the idea of being in a relationship. Plus CT/NY for guys is far...the wrong kind of guy likes close proximity to satisfy his whims. Go on and enjoy YOUR summer :-)

Headless Horseman said...

When I pull my head out of my ass, can we go back to being pen pals?

Jenny From The 'Brook said...

Anon #1: Glad that made you laugh -- made me laugh too when I wrote it.

Exec Wife & Anon #2: Thanks so much for the advice. Check out my post from today, you'll see the story had a happy ending, and all this bullshit was actually worth it!

Headless: No.

kara said...

oh my god! hilarious! this writing brings me back to the very clever days of dell publishing when emails like this would fly back and forth all the live long day!!

Jenny From The 'Brook said...

Kara: Great to hear from you! Love that you read the blog!!!