#20: The Wingman Chronicles Part II: Playing the Ivy Leagues

The second rule for wingmen to remember as we hit Part II of the chronicles: Karma.


Alright, karma's not really a rule, but this is hardly the blog for discussing religious doctrine and I'm really bad at writing intros, so screw off. Point is: Be an attentive, unselfish wingman and the pendulum will swing back in your favor.


Having successfully wingmanned my lady Red a chain-smoking, blues-singing rocker, I was feeling...good. I was back on the scene after years missing in action, had helped a dear friend score and had only stepped marginally closer to lung cancer (note to self: corner next prospect in Whole Foods, not on a smoking patio) in the process. But how hard it is to help a model, one who swigs Guinness in dive bars, get laid by a rock star? Wingmanning Red is like winning the Special Olympics when you have both...nevermind. What I mean is, I had to test my success and make sure it wasn't just luck.


It was time to draft Ariel.


Ariel is my original wingman. I learned the definition of the term from my exploits with this girl, a kinetic ball of energy blessed with the gift of gab, a contagious staccato laugh and a pair of perky C-cups which have not moved so much as a centimeter south in the last decade. (And I know "Ariel" is an asinine fake name, even for a blog. But for eight years it's been her bar alias...and dudes buy it. Not one man has ever called shenanigans on that ricockulously fake name, stolen from either an animated mermaid, a Shakespearian nymph or a bottle of non-alcoholic wine, depending on how highbrow you like your pop-culture references.)


If Red and I are a perfectly balanced yin-yang of feminine mystique, Ariel and I are the Boondock Saints of wingmanning--a rogue team of petite, busty, hustling vigilantes set loose on an unsuspecting world. We've infiltrated the West Point Military Ball, commandeered an entire winery and its reserve stock for a private tasting, talked our way into a closed party for a cosmetic surgery mogul we did not know to drink $300 worth of his champagne, used the infamous "one phone call" to dial up the other from jail...in short, she's that friend.


We picked a nuetral, unassuming bar to meet at for a night of tactical planning. Our only mission: celebrate both being single (at the same time!) and discuss battle plans for the following weekend's Wingman Reunion 2009. I even wore a scrubby hat to keep booty at bay.


Ariel and I had been sitting with our pints, planning animatedly, for about half-an-hour when a pretty, square-jawed, tall and wholesome type with a full head of thick, chestnutty hair and bright blue eyes sat down at one of two empty stools at our table.


"Hi," he said.
"Hi," Ariel said.
"Hi," I said.


We all stared at each other for a moment. "Good talk," I finished.


His mouth spread into the sort of sweet, Mentadent white smile that can only be grown (organically) in midwestern fields. I had been ready to fire a dismissive snark-barb at him as soon as he sat down, but the genuineness of that smile disarmed the table. Ariel pulled a thick cascade of hair over to one side of her face, using the movement to flash me the "he gets five minutes not to say anything stupid" look. 


He did not say anything stupid. His name was Tommy (-2 points for not dropping the "y" after college); he was a Yale (+5 points) graduate (+10 points), in the city for a long weekend (+5 points) before returning to his job as a landscape architect desiging parks for a community improvement firm (+50 points). He loved Aimee Mann (WTF?? -5 points), black and tans (+1 point) and the journalistic stylings of Matt Lauer (no points either way). His wingman for the night was a pixie-girl named Tracy, who bonded with Ariel in three minutes flat before buying them both a beer. At the bar. Leaving Tommy and I. Alone.


Three brews, one shot and two hours of conversation later, Tracy and Ariel still hadn't returned. I could see them at the bar over Tommy's shoulder, heads pressed together like sleeping marsupials. Plotting. They're plotting.  Tommy cupped his hands over mine and I didn't pull them back. (What? They felt nice.) Ariel appeared a few minutes later, collecting her purse while whispering into my ear.


"Full report: great guy with history of monogamy and chivalry. Has been talking to Tracy about needing to meet you since you walked in. Monday he goes back to his house, which he owns, upstate, so you won't have to see him again if you don't want to. He will not try to rape, murder, kill, or fuck you if you go with him to Tracy's apartment, which is two blocks away. My spare keys are in your bag and the phone is on loud case you need to eject at the last second," she spat sotto voce while pulling on her coat.


"Where are you going?" I hissed back, watching as Tracy also whispered something into Tommy's ear while pressing a set of keys into his hands.


"Downtown with Tracy to meet her boyfriend, who she is staying with for the night so Mikey can ask you back to her beautiful Hell's Kitchen apartment with a balcony," she replied. "Just say yes." And just like that, Tracy and Ariel were gone.


Which is how I found myself on a balcony with a pretty Ivy League grad who designs parks for underprivileged families kissing all over my face, whispering how beautiful I was in spite of my truly epic hat-hair. True to Ariel's report, there was no sex pressuring when the night officially ended with an exhausted collapse into Tracy's bed. No "just the tip," no casual boob-grazes--just my weary head on a pillow. Next to a full-blown, domestically-raised adult male sharing the bed who didn't try and cajole himself into any of my orifices. (Gay, or just good? The Aimee Mann thing threw me.)


Tommy woke me in the morning (remembering on his own that I had to be up for a heinous Saturday morning meeting at work) with a text message from his side of the bed: "You are breathtaking in this moment." I still cannot decide whether this was a ripe slice of cheddar or the sweetest thing ever.


Then he made me breakfast.


I walk-of-shamed it to the office, survived the meeting, went home, tried not to think about how kissing Tommy didn't feel like kissing Alex, and crashed. Sunday night, my phone lit up with another text from Tommy:


"You are my New York. Thank you."


I texted something, but not to Tommy: "Well played, Ariel. Well played."