Flirtation Technique #308: Do NOT Talk About Your Days as a Wild Child

Lovelies:

I had two dates this weekend--and three parties to attend--but maybe what's worth discussing today is Date #1.

All week, I'd been planning to take Friday afternoon off so I could make a solo trip to The Guggenheim, where I wanted to check out the retrospective of works by Vasily Kandinksy (opens in new tab), the great existentialist pioneer of abstract painting. (I love modern art. If you open yourself up to it, it makes you have lots of lovely emotions, which lead to some interesting thoughts. *Plus, there are always lots of sexy Italian tourists hanging around the museums.*)

But on Thursday afternoon, a museum-outing partner presented himself.

A certain someone--someone I met very recently, someone I maybe had a little crush on, someone I might even have drunkenly smooched a little--texted to ask if I'd like to do something artsy over the weekend. Delighted to hear from him, I invited him to come along with me.

(Guys, please don't yell at me for not mentioning this mystery man before, but I wanted to play this one closer to the chest.)

Unfortunately, I had insomnia on Thursday night, probably because I was so nervous about seeing you-know-who. So, by the time I met up with him at 430, I was pretty spaced-out.

He'd warned me he'd be dressed up for the holiday party he was going to later and true enough, he was looking ridiculously adorable--or maybe adorably ridiculous--in green cords and a maroon blazer, with a candy-cane boutineer.

Much as I could appreciate the outfit, I was too tired to really get into the exhibit, or to say anything interesting as we circled The Gugg. Chris Kringle held up his end of the bargain admirably, however, making me laugh by cracking joke after joke. Like: "That one there, I could see that one hanging up in a strip mall restaurant called 'Salsa Mexicana.' ... But that one would be perfect in my podiatrist's office."

After leaving the show, we walked over to the Central Park reservoir. Looking across the purple water at the buildings on the other side of the city, twinkling in the distance, it was as if we weren't actually in New York but instead at some distance away from the mystical city in our vision; it seemed to promise that we could get there it if only we kept walking ... but, of course, the place of our dreams would only disappear if we tried to reach it. So we went to a diner, hoping comfort food and coffee would give us the push we needed to keep going in The City That Doesn't Sleep.

I don't know if it was because I was so pooped, or because we just don't have as much chemistry as I thought we might, or what, but our conversation over grilled cheese sandwiches felt a little strained, less than smooth. ... As a result--perhaps because I was nervous--I did something rather regrettable.

Before I explain what it was, let me say that when I was younger--in my mid-twenties--whenever I felt a date was lagging, I would start telling crazy stories. Like the one about the time I snorted coke with some bar owner, or the time I snorted coke with some limo-driver who picked me up off the side of the road as I was trying to hail a taxi, or the time I snorted coke with some random dudes I met in a bar in Berlin. (Nota bene: I do not snort cocaine or do any drugs these days. And while I'm not going to moralize, I will say I feel better off without that stuff in my life.)

I'm still not entirely sure what my subconscious motive is, when I talk about my days as a wild child. Is it because I have a guilty conscience? Is it because I get so worried that I'm being boring I feel the need to prove that far from being boring, I'm a complete lunatic? 
Is it to shoot myself in the foot on purpose: to give myself an obvious explanation for why someone is not that into me--because I make myself sound like a crackheaded floozy?

Whatever the case may be, I found myself telling Señor Kringle about two things I'm sure I would've been better off NOT mentioning: the time I kissed a cab-driver (opens in new tab) and the time I snorted coke with those dudes in Berlin.

When the check came, Mr. Kringle did very nicely pay it. But he didn't suggest we go somewhere for a drink. (Maybe I could've have suggested it, but it honestly didn't occur to me.) And we said good-bye without any discussion of hanging out again. Which made me a little sad.

Admittedly, on our date, I didn't feel a huge connection. Regardless, I'd liked him so much the first time I met him that I was hoping we might have a little more of a future ... but given the fact I haven't heard from him since then, it's clearly dead in the water.

Point being, I think it's a REALLY bad idea to talk about your wild exploits from yesteryear (or from the previous weekend) on a date. 

I'm sure you sexy, charming, graceful lovelies don't have to be told this.

And yet, a few weeks ago, at a dinner party, a very good friend of mine told a wildly inappropriate story about a recent hook-up she'd had--despite the fact that a dude she had a huge crush on was sitting right next to her, listening to every word. I took her aside later and pointed out that maybe it wasn't such a good flirtation tactic. Too bad I failed to take my own advice, huh?

Anyway ... do any of you have this same problem--of offering up TMI to the person you're enamored of?