Have we met?

If you find me charming, funny and confident, then the answer is no. Although, we might have emailed. Why? Because in terms of personality, I'm Don Draper ... electronically. In the flesh? Not so much.

Welcome to my personal hell.

Here's the deal: When I email a gal, I'm imbued with all these crazy powers. Confidence! Wit! Charm! On my Powerbook or my iPhone, I'm George Clooney at a cocktail party. On a date, without my assorted Apple products, I become ... the Mac guy.

It's my own personal cross to bear.

Now, aside from the fairly obvious reasons I might seem better "on paper" than in person (I'm a writer, I'm a Taurus-Gemini cusp, I'm not distracted by the presence of your boobs, etc.) is that I'm too good at the big email build-up. It may be that my sense of comic timing from faceless G-chatting is so well honed that I never live up to the expectations I've created.

On dates, you're expected to maintain the same level of charm and confidence, with additional obstacles like using utensils to successfully deliver food to your mouth while maintaining frequent eye contact and engaging in small talk. I can do all the above with family and friends, but put me across from a woman I could potentially have sex with, and suddenly I'm stirring my wine with a salad fork.

What the crap?


If you just had the audio files of my dates, you'd swear you were listening to a live audience watching "Paranormal Activity" for the first time. Lots of suppressed gasps, audible wincing and, of course, the "Don't go in there!" when my date watches me waltz into the ladies' room.

On email, I'm so confident I can willfully act like a goober and it still somehow works. You write stuff like "Hey, Thursday night sounds great, looking forward to it. Where are we meeting again?" and I'm all "It's that bar on 1st street, at the corner of 1st street and 1st avenue -- don't try to remember the name, we'll just call it 'I'm Firsty' so you remember," and then I get a "that made me LOL" and I'm like "Lean On Lobsters? Why would you do that, they pinch!" (Yes, the above description is hypothetical/ridiculous and pretty dorky, but like I said, it's worked.)

Then we get to the actual date and my mind just goes into this hellish overdrive due to nerves. I can't focus on what she's saying, which inhibits my ability to ask informed questions, which then reduces the date to the boring, mindless small talk that bad dates are made of. She mentions something potentially interesting, like a year spent working in Cambodia, but I'm only half listening because I've just dribbled olive oil all over my lap and end up going, "Oh Cambodia, that's near Thailand," like some kind of teenage idiot stoned on whippets.

So, I go from slinging wit in my emails like Oscar effing Wilde to having all the erudition of Sloth with a mouth full of Baby Ruth. My inability to focus on the important things is coupled with my insane focus on stuff like the weight of my arms and hands (What the hell is this about? Get me on a date and I'm thinking, Whoa! Where did these arms come from? What do I do with them? Oh God, why am I resting my chin on my palm like this? Who am I, Mitch Albom?)

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Then as the drinks flow, the motor skills are like "Hey man, good luck, we're heading over to I'm Firsty's for pints."

It's not just me. I have girl friends who are spectacularly funny and continually make the dudes they email laugh so hard that little bits of pee shoot out. Then when they show up on the actual dates, they act like Charlize Theron from "Monster."

My hilarious good friend (and an editor at this very website) has this problem where her reliably guffaw-inducing Twitter feed leads strangers in the N.Y. area to ask her out for beers, which she occasionally accepts. At said meet-ups, all her considerable intellect and hilarity liquefies; she becomes a vodka-glazed Thor whose idea of conversation is to armpit-fart "Party in the USA."

Another friend's substantial text-message wit and email charm devolve so badly on dates that I will throw her an actual party if she ever manages to make it through one without nervously talking about thigh chafing, her latest pap smear, or the fact that she hasn't gotten laid in so long she's regenerated her hymen and grown a second one to keep the first hymen company. She'll call me and be like, "Hey, I didn't mention poop in the first 20 minutes!" and I'll be all "Yaaaaay, progress!"

I think what I'm realizing is, sadly, the best version of some of us really exists in Rich Text Format. Calm and cool with a keyboard, full-on loco with a menu. "I'm making too much eye contact oh God she smells like springtime did I leave my oven on? I'm going to die alone I'll have the candied pear salad thank you oh Jesus H. Christ what kind of man orders a candied pear salad does this place serve hemlock CHECK PLEASE."

People used to have epistolary romances all the time. Can we be sure, however, that those torrid lovers who stoked their romances with longhand letters didn't also suffer from the awkwardness of an actual, live date? Isn't it possible James Joyce met Norah at a bar after writing her some steamy pine-y missive and was all, "So ... you're a seamstress? Oh, whoops, right, I asked you that already" and then knocked over the saltshaker? Or what about some super-awkward encounter between two heated pen pals where the middle-aged and extremely "I think I'm in love" lady shows up at a hotel only to be like "Oh my God, you're a woman, George Eliot?"

I've had female friends suggest that I do this date-ruining on purpose, that I'm self-sabotaging because I'm not actually ready to be in a relationship. It's food for thought (which, were I on a date, would somehow end up in my sideburns), but I don't buy it. I just can't quiet my mind down when I'm mug-to-mug with a pretty lady like I can when it's my stupid laptop staring me in the face.

So, maybe next time you find yourself confused as to why the guy who's been making you shart with his clever OKCupid messages is now making you uncomfortable over pâté, give him a break and a little bit of time to get his act together.

As for those of us afflicted with this "IRL syndrome," I hope we can figure out a way to set up circumstances in which we can be the charmers we are online. Perhaps this is as simple as just reminding ourselves that it's not all that big of a deal -- on a date, just relax and remember how a fork is used.

Or maybe I should just say "f**k it" and get a prison pen pal.


[Redacted] Guy is the resident Single Guy writer for Lemondrop. His smooth jazz album, "Convicted Sax Offender" (featuring his number one hit "Finish Your Coffee and Get Out of My Apartment, I'm Meeting Friends for Brunch ... Baby" ) is now available through Time-Life Records. Sorry, no CODs.

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