Thursday, January 6, 2011

The entrepreneur

Have I mentioned how awesome it is when guys read my blog first, then want to date me?

Oh, I have? Multiple times? Well, it bears repeating anyway:

It's awesome. It's fucking SUPER FANTASTIC AWESOME.

It's awesome because for starters, I don't have to tackle the awkward "Oh-dear-how-am-I-going-to-broach-the-topic-of-this-blog" question with them. They already know the score. 

And to meet a guy who knows that A) yes, I am going to write about you; B) yes, there are probably going to be other guys that I'll be writing about (at least until the topic of exclusivity is broached, which realistically would not be for a while); and C) acknowledges A and B and throws his hat into the ring to date me anyway??? 

Well, that just takes a set of brass cojones the size of the goddamn Capitol Dome. You, sir, are an American hero, and for that reason alone I am automatically insanely attracted to you and ready to practice how to make babies every hour on the hour. 

Also, how could I not be attracted to you, what with your clearly discriminating taste in literature? I love being appreciated for my writing. Furthermore, since they've read this thing and have done their homework, they can use it as "How to Impress Katie: A Handbook":

Finally, beyond any one man in particular, I'm finding that the dates I've gone on as a result of the blog have actually been significantly better than the dates I've secured from the various online dating sites. I'm realizing that the kind of guys I'm attracted to -- outgoing, adventurous, uproariously funny -- are NOT trolling the web looking for dates. They're out on the town, making it happen, because they're confident and cocky, and they come fully equipped with those aforementioned brass cojones.

And the entrepreneur, who I met for drinks in Old Town on Tuesday night, is just that.

So, technically, I didn't exactly meet the entrepreneur through my blog. Technically, I met him through Twitter, which is connected to my blog, but is a whole different animal. He followed my tweets; I followed his back, which I believe to be proper Twitter etiquette, or "Twetiquette" (holy shit, I feel SO dumb writing this paragraph). At some point, he sent me a "direct message," and our subsequent exchanges began to get flirtatious.

Finally, the entrepreneur sent me this: "So guess who came up in my suggestions?"

For those who've never been on Match, each day it sends you a round of different people in your area who it thinks you might be interested in. This would not be the first time somebody has been sent my profile and recognized me from my blog. I mean, that's me at the top in the banner, so it's not hard to figure out. It happens.

I hadn't seen the entrepreneur's profile -- I'm somewhat delinquent on checking my Match account -- but his Twitter messages to me all seemed to be sent with a cocky smirk, which definitely sparked my interest.

"Awesome. You should totally take me out then," I responded.

We continued messaging back and forth for a little while until we finally agreed to meet up Tuesday evening. The entrepreneur suggested Columbia Firehouse as a destination, which I'd never even heard of before. But, I love trying new places, so that was a win in my book.

I'd gotten exactly four hours of sleep the night before, and not for lack of trying -- I'd taken a sedative and hopped into bed at about 8:30, but my attempts at slumber were futile. I took to Twitter to bitch about how Sominex is a waste of money and how tired I was going to be.

The entrepreneur, of course, reads my tweets, and sent me this message: "Do you always have insomnia the night before a BIG DATE???"

When I read that, I actually snorted. Yay, he's funny. This was boding well.

I was about 10 minutes late to the bar, and when I walked in, the entrepreneur was already waiting for me. And ohhhh... blue eyes and a strong jaw line -- he's cuuuuute!!!! My inner 'tween squealed a little. At the same time, old insecurities threatened to wage war inside me... cute guys always make me lose my nerve a little.

He asked me if I wanted a drink, and we sidled up to the bar together to pick out cocktails.

"By the way," the entrepreneur said while we were waiting for the bartender, "for someone who only got four hours of sleep, you look impeccable."

And with that, a wave of confidence and relaxation washed over me. What a great compliment!

We took our seats again and started talking. The entrepreneur grew up in New York, but actually went to college in Ohio at my college's biggest rival school. He's a bit older than most of the guys I've gone out with -- 37 -- but he looks much younger so you'd never know it.

Right now he has a management consulting firm, but he's started several other business ventures throughout his adult life -- some successes, and some total failures. And as he was telling me all this stuff, I was so impressed. Not because he was clearly doing OK now, but because he'd had the balls to start something, to DO something, to take a risk and fail spectacularly. That brand of guts is an admirable quality, and something I wish I had a little more of in myself.

After a few drinks, he asked me if I'd ever been to any of the speakeasies around town.

"Isn't there one right around here somewhere? It's called PX, and it's actually on my list of places I want to try," I said.

"Let's go there," the entrepreneur said.

I always like dates that change location. It's like a choose-your-own-adventure novel. And more than that, it's how I gauge whether things are going well. Things were clearly going well.

Unfortunately, PX is closed on Tuesdays, so we were thwarted in our aims there. We continued walking down King Street until we got to The Majestic, and we settled into seats in the window to have another round of drinks.

By that point, we'd gotten all the major get-to-know-you points out of the way (jobs, family structure, basic life outline), so we just started talking about a bunch of random, crazy shit. I can't even remember what all topics we covered. Well, one of them was "tell an embarrassing sex story," the results of which I will not be sharing with you people (sorry).

The entrepreneur is funny. Genuinely, laugh-until-you-cry FUNNY! And as I mentioned earlier, that's something I'm desperately searching for in D.C., which may as well be called The Land of the Serious Suits. Nobody, and I mean NOBODY, has a sense of humor here.

And, I should note: Everybody says they're looking for someone who can make them laugh, but what that actually translates to for most women is "I'm looking for someone who makes me feel at ease." For me, however, I actually mean "makes me laugh" -- I want someone who makes me laugh until my stomach hurts. No, not just that -- I want someone who makes me laugh until my stomach hurts and I can't breathe. No -- I want someone who makes me laugh until my stomach hurts, I can't breathe, and I'm peeing blood. Yeah, that's about right.

The entrepreneur TOTALLY fits the bill in that respect. I heartily enjoyed every freakin' second I was on this date. I was having such a good time!

Additionally, we got on the subject of online dating, and the entrepreneur mentioned that he'd taken his profile down because the people he was meeting online were not the kind of people he was ultimately interested in -- he echoed my sentiments on wanting to meet people who are out on the town, soaking in life. Sweet.

He asked me if I wanted to order food, which made me kick myself a little -- I have taken to eating a full dinner before dates where the food question is left ambiguous. By now, I've been in WAY too many situations where I have not eaten and discovered dinner was not, in fact, part of the plan, and then ended up a sloppy mess as a result of a night of drinking on an empty stomach. But he offered, and I would have loved to have taken him up on it.

The entrepreneur did order something for himself, and we got another round of drinks. And while I was having such a good time that I was mostly oblivious to this happening, one by one, other patrons began paying their tabs and disappearing out the door. I only noticed that the restaurant was down to three people -- me, the entrepreneur and the lone bartender -- when we took a break to use the bathroom.

We chatted so long we shut the place down.

We left, and the entrepreneur walked me to my car, several blocks away back near Columbia Firehouse (which I TOTALLY want to go back to -- it's built in an old-timey fire station, how cool!).

 I told him what a good time I'd had, and he leaned in and kissed me goodnight. My inner 'tween was doing a lot of squealing that night.

So, my FOUR-HOUR date with the entrepreneur made me thank my lucky stars I caved and joined Twitter. He was fantastic! I texted him immediately when I got home to say again what a great time I'd had.

"Now that we're over the first date hump, we'll RAGE next time!" he texted back.

I'm not entirely sure what all that means, but I'm looking forward to finding out.

Though, one caveat: He was fun and exciting and awesome, but the entrepreneur strikes me as one of those forever-bachelor types. Which is totally within his rights to be -- it just means I have to work on managing my expectations and not getting carried away.

But... a few more dates couldn't hurt... right? Right?


  1. He doesn't get one of your Mom's 37 and single (and cute), what's wrong with him?

  2. Well, I think I already outlined it in my second-to-last paragraph.

  3. Sounds like a pretty good date! I actually wanted to ask you out after reading your blog, if for nothing more than enjoying a nice date with an obviously funny woman and being written about, but alas I found a girlfriend before I had that chance.

  4. A guy who makes you laugh is definitely a plus, because guys who are too serious are often boring.

  5. I love it when women praise with a thanks after they get home and the morning after a date. Direct feedback is awesome!

  6. Man that sounds like an awesome date.

    Any date that lasts longer than an hour, and is enjoyable is a good one in my books.

    Looking forward to hearing more about the entrepreneur!

  7. I totally agree about the "make me laugh," that's definitely at the top of what I look for in a guy. You're right, I don't want to "feel at ease," that gets boring; however, having someone that can make you laugh until it hurts never gets boring. Sounds like a fun time!

  8. GO FOR IT. sounds all-around amazing!


  9. Love the great date and giddy gushing about it :) The Entrepreneur sounds like a great date- with hopefully more great dates to come!

  10. OMFG! How incredibly awesome is this?! I get your '...make me laugh so hard I pee blood comment,....' -I'm the same. Who knew- PA/OH - we must seek the same type then! I think it's fabulous and can't wait for the next date!

  11. It's like we challenged the universe saying the men we want don't exist, and then they fell into our laps! Well, sort of. Maybe. Next time I see you I'm asking you about your embarrassing sex story, btw.

  12. this is refreshing...funny AND handsome men in dc? woohoo!

  13. I’m taking credit for this date because I told you to join Twitter. I propose you buy me a cocktail at the Majestic, and we go Dutch on dinner because their food is scrumptious.

    Megan K.

  14. I think you'd help your chances if you learned to bat or throw left-handed. Southpaws are always in demand.

  15. Duly noted, Kyle. I'll work on that for the next company softball season.

  16. Of course these dates are better...they already know tons about you. They can tailor the conversation towards stuff they know excites you. In a regular dating situation it takes time to come up with that info. Not that I'm hating, because I'm not.

  17. Love dates that go on for hours! Sounds like a very good first date. I look forward to reading more.

  18. Very Nice stuff. I have a blog too:

    See you tonight, I guess!



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