The Trials And Tribulations Of Being A Wing Woman

February 22nd 2013

“Listen to me. I just broke up with my boyfriend and I just want to get fucked up and hook up with someone. Are we clear?”

I knew this phrase. And I knew it well. Spent many a weekend providing my most premium wing woman capabilities to every heartbroken/horny friend near and far.

Been a while since you’ve been slammed? I got you.

Need a confidence booster post batshit ex? I got you.

Hot human on the other side of the bar that just so happens to have janky looking friends but please talk to them because this human is so beer-goggle hot that I might drown my sorrows in a  bath of drunken pizza sauce later if you don’t do this for me? …I got you.

But this night.

…this night was different.

Sure it started with the same request. But the ending? Well. The ending resulted in a full-blown sprinting wasian down 3rd ave at approximately 6.a.m in New York City watching the sunrise in between sky scrapers as I ran for my life in an unbuttoned  American Eagle pea coat.  I was desperate. I was scared. I was delusional. I was a little hungry. It should have never happened. But it did.


“Listen to me. I just broke up with my boyfriend and I just want to get fucked up and hook up with someone. Are we clear?”

Okay. Yes. I can do that. Wing woman hat officially on.

She ordered a round of shots, raised her glass and said “Let’s consider this night as a giant fuck-you to Andrew.”

Oh no.

She tipped her shot back.  I finished mine in two sips (like a bitch) but once I lowered the miniature glass I realized

 She was nowhere to be found.

Excuse me, man in an inexplicable top hat by the bar, have you seen the girl I was just talking to?

Yeah. Over there by that gaggle of Mexicans.


I pushed my way through finance hotties and sequined schlores just in time to hear her say:

“I fucking love drugs and caramel ice cream. Tell me more!”

Wing woman hat – activate!

“Hey, Tori! I have to go to the bathroom. Come with me?”

 Mexican #1: “Porque girls always have to go to el bano together?”

(Men…let this go…just…let it go.)

I grabbed her hand with wing woman force telling her that she was better than drugs and ice cream banter at a bar. That our mission was to get her hanky panky. Not make illegal treats with strangers on our off time.

She looked at me with cross-vodka eyes and said “hehe haha hoheha hah okayyyy”

Hand in hand I bee-lined for another location of the bar and felt myself <<<< pulled back immediately.

“There he is.” She said.

That guy. I want him.

At first glance he kind of looked like a young, buff Brad Pitt lightly sprinkled with fresh H2O that was casually cascading down his abdominals like this:

Well done beer goggles, well fucking done.

Well done beer goggles, well fucking done.


…But in retrospect resembled that of a fatigued Draco Malfoy/Miley Cyrus hybrid with unkempt hair that looked like this:

You win again, beer goggles.

You win again, beer goggles.


But these details were apparently irrelevant in the inebriated vision of my dear friend Tori. She scampered across the premises and upon their immediate make out session (fueled by Gin and Tonics and a few Stella Artois) I realized it was in my wing woman contract to forcefully converse with his default friends.

“Hey so. I’m Olive.”

There were two of them. Both wearing suits. One was about 6’5 with oversized teeth and a haircut that said “I’m a terrible person.” While the other was a mid-sized banker with questionable hygiene that said “I’m 2nd choice and I know it.”

Big Teeth took the liberty of overtaking the conversation, stepping in front of 2nd choice and chatting about things I hated like tax increases and the floatation of cats.



Be a team player Olive. Tori needs this. Stop staring at his teeth. But why are there so many? No NO no stop STOP staring. Subject change. SUBJECT CHANGE.

“Hey what’s that? On your jacket?”

He peered down and smiled. “Oh this?” He turned it towards me. “It’s a button that says ‘Save the Children’. I just came from a charity event, must have forgotten to take it off!”

So this but like...on a button.

So this but like…on a button.


Oh no. I feel tequila brain coming on. Damn those two sips. Don’t be a rude bitch. You kind of get a bitch rudey when you drink. Oh no. Did you just say bitch rudey? Now my consciousness is fucked up too and it can’t talk right either! KEEP YOUR SHIT TOGETHER YOUR FRIEND NEEDS YOU. Say something, ANYTHING.

“Oh please. You’re full of shit. You totally stopped by your Crate and Barrel coffee table, opened up the damn drawers and pinned that baby on your jacket on your way out the fucking door. PUN INTENDED. You’re a sick bastard thinking you can pick girl up with that shit.”

Note to self: You’re the worst.

II He paused II

Looked at me and said “So…what are you drinking?”

Good god, Big teeth is giving me redemption! Be classy, SAVE YOURSELF.

“To be honest, I’ve had so much to drink tonight, I can honestly tell you that I’m just as mentally handicapped as you’d  like me to be. Congrats!”

You’re a fuck up.

I knew he believed me. He even noticed me periodically glancing at my batshit friend who was currently smashed against a wall with a stressed out Draco. He knew I was trapped. Forced to linger due to my wing woman ways. Pleased with his newest hostage he began to say a series of things that I wish so badly that I made up…but I didn’t:

“I’ll get you a drink”

“I said I don’t want anything”

“Yes but my goal is to get you more drunk so this will be easier for me to take advantage of you”

he said as he snapped his fingers at the bartender and had 2 vodka sodas strategically placed in front of us.

We made vengeful eye contact. I grabbed the drink, and did a back pass to the gaggle of Mexicans we met earlier. Big teeth was not amused. Realizing his child button tactics and date rape ways were as useful as Kristin Stewart at the Oscar’s, he attempted a more forward approach. Literally.

“Listen, Holly? It’s Holly right?”


“Cool. Listen Holly. I have something very important to tell you.”

He moved in closer.

Oh no. Tequila goggles officially out of commission. His terrible hair is now too close for comfort and interlocking with my lustrous waves.

He leaned in and whispered something in my ear. Something I could barely hear above Beiber’s latest backbeats. But I managed. He said:

“I have a very big…you know…dick…it’s like…really really big. Like…dangerously big.”

“Oh gross.”


“Yeah I said gross.”

“I mean…I thought girls like that.”

And the I said in an elevated voice for the whole bar to hear:

“I mean girls like penii for sure but not when you make them sound like a Semi-automatic rifle. Like christ man. Girls wanna hang out with them not die. And by the way, “dangerously big” doesn’t mean one size fits all. This ain’t a plush robe. It’s a fucking weapon.  So keep that shit to yourself!”

Tori looked at me.

Draco looked at me.

2nd choice looked at me.

Mexican gaggle looked at me.

In response to my unwarranted statement that silenced the bar,  2nd choice broke the ice with a –

“Sooo would you ladies like to come back to my place with us?”

This was it. This was my way out. My wing woman duties were coming to a near end. Tori got her make out. I destroyed my charm and his dignity in a matter of milliseconds. The perfect time to exit! I gleefully started to say  “Absolutely no-” Until Tori cut me off and said  “OH WE’RE GOING” and I watched as the door swung behind her.

I glanced down at my phone


4:33 am


<<Tori ran after Draco << I ran after Tori<< Big teeth ran after me >> No one ran after 2nd choice.

Everyone ran anything but a straight line back to 2nd choice’s apartment and upon arrival Tori looked around and noticed that somewhere along the brief 5 block commute, Draco was nowhere to be found. Her response was as follows:

“THE FUCK IS THIS SHIT? THE WHOLE REASON I CAME TO THE PLACE (hand slam on counter) WAS TO HOOK UP WITH YOUR FRIEND (drop kicks the refrigerator) AND HE’S NOT EVEN HERE! (Tosses hands up in the air with utter disbelief) THE FUCK DID HE GO?!! TELL HIM TO COME BACK NOW OR I’LL DESTROY THIS POPSICLE STAND (fast pitches an orange off kitchen counter onto the nearest couch)”

Freshly threatened and slightly panicked 2nd choice immediately called Draco on the phone and I heard his muffled voice say this

“Dude where the fuck did you go you gotta get back here RIGHT NOW. This bitch is going crazy and I’m afraid she’s going to tear shit up…she’s got a loco look in her eyes man. Please PLEASE just come back. What? Oh shit…yeah I guess just bring them…alright cool man. See you soon.” Click.

Big teeth offered to escort me to the next room to drop off my coat, but as I divorced myself from my beloved American Eagle Pea coat (I judge myself) and reached out my hand to give it to him, he tightly clasped onto my wrist instead and said

“You’re going to put your hand in my pants now.”

 – Cue in drunk Olive. –


“I know you want this. We talked about it at the bar, remember?”

“…I’m not so sure that’s how that conversation went…”

“You were staring at me all night.”

(Note to self: Teeth staring = often mistaken for love.)

“I really couldn’t see anything in there. Real foggy. Coulda been looking at anything, really.”

“Put your hands in my pants right now.”

“Why are your teeth so big?”


“You know, Big Teeth.”


“You see, Big teeth, even now in the sheer epitome of ill-advised decision making, I have to say, I could not want you any less than I do in this very moment. And that’s bad isn’t it? Yeah that’s kind of bad. That’s bad.”

“Jesus Christ, how drunk are you?”

Olive officially on the floor. 

I didn’t pass out.  But I did pretend. Indeed, in attempts to be a good wing woman and kill time for Draco to make his dramatic return,

I faked my own unconsciousness on a strange man’s living room floor as a casual layover to the night that was still…not over.

Big teeth stepped over my body like a gentleman and exited the room. I stood back up and joined immediately after. As I entered the room a suspicious 15 seconds later, 2nd choice approached me by the kitchen counter and said

“Listen. I’m not trying to be a dick. But. My boy, Collin? Who was hanging out with you in the other room?”


“Yeah…well…he has a fiance…and he’s getting married in 2 weeks.”



Before I even had a moment to react Big Teeth immediately popped up from the couch, grabbed his coat and screamed “Fuck this shit. I’m leaving. HOW COULD YOU MAN!”

So I totally helped the situation and said “Bye bye big teeth say hello to your fiancé for me!”

He looked at me with fire in his eyes. And then looked at 2nd choice with lava in his eyes and said

“Have  a good night man. And by the way, YOU ARE NO LONGER MY BEST MAN.”

Door Slam.

My wing woman duties were going terribly awry. I had faked my unconsciousness, compromised a wedding and destroyed a bridal party, all in a span of 7 minutes…this has to end. IT HAS TO END NOW.

Door open.

Draco was back. Tori almost had a metaphorical ulcer upon his arrival.

But wait.

There’s more.

Draco didn’t close the door behind him because, well. There was someone else that was here too. Someone that he brought. Someone that he introduced  to us as:

His girlfriend

Tori looked at me.

Then over to Draco

Then back to his girlfriend.

2nd choice once again broke the ice and said

“So you guys wanna go play beer pong in the other room?”

Surely. SURELY this would be our cue to leave. Draco showed up with his girlfriend, I grenaded a wedding, Tori’s eyes were practically rolled in the back of her head. I’m just going to do it. I’m just going to say it

“I think we’re actually going to head -” until Tori said “OH WE’RE PLAYING” And I watched as the door swung behind her.

Check the phone

5:02 A.M.


Team 1: 2nd choice and Tori

Team 2: Draco and Girlfriend.

There I was on the couch

Witnessing Draco playing beer pong with his latest infidelity, WITH the woman he just inflicted infidelities on.

This was all sorts of fuxed up and I just couldn’t do it. I really just think that –

I’m instantly passed out on the couch.

I start dreaming about this tsunami in Korea. Rihanna’s there. She’s wearing yellow socks and she says hi.  But then somehow I end up in this hotel and the bell boy turns into a dog and this doesn’t make any sense but it’s a dream so in this moment it makes a lot of sense that my bell boy is a dog. And the dog asks me if I want fresh towels and I say yeah sure thanks! And then he asks me if I want to go and I say what? I just got here. And you gave me towels. And he says yeah but do you want to go? We gotta go. It’s –


I popped up from the couch immediately. Tori is shaking me incessantly. Tells me it’s 5:46 am and that she’s realized that she doesn’t think this love with Draco is going to work out so well. That she doesn’t see his girlfriend leaving anytime soon so maybe next time.


Ask no questions. Ask none at all. I grab my pea coat and attempt to bee-line out the door only to see Tori making out with 2nd choice. FOR THE LOVE OF GOD.  I pull her away. She tells me “GEAR CHANGE! I’M GONNA STAY HERE WITH THIS GUY.”

I tell her that I want to do violent things to her and that we’re leaving immediately. She finally agrees. I spend the lengthy cab ride home listening to her send 16 voice mails to ex-boyfriend Andrew all resembling something like

“Heyy! It’s me! Just wanted to tell you to go fuck yourself and die. Olive says it too. Taxi driver says it twice. Kiss my ass! Bye!”

16 times.

We arrive at her intersection. Tori offers to pay but can’t seem to find the right credit card. I’m getting antsy. I’m…getting….an….tsy.

“Nope this one doesn’t work either! hahaha let me try another one!…Nope…not this one…Hmm…not this one either.”


I kicked open the cab door. Jumped into the nearest intersection on 3rd ave. And fucking ran. And ran. And ran. And ran some more. I was running at tequila speed whilst I watched the sun rise in between skyscrapers until I finally reached my upper east side abode. I crashed in my bed, my eyes heavy with cheeseburger cravings and sudden loss of dignity. Why. How did this. Where did I? Note to self: Light wing woman hat in flames tomorrow – and recommend Colin a dentist. Where did that dog go? Why is Rihanna wearing yellow socks? I’m falling asleep. Tsunami?

It’s instantly morning

I wake up from a text. It’s Tori. It says:

“Hey thanks for going out with me last night. I appreciate you being my wing woman. First time I had fun post break up. You’re awesome.”

And I realized that in that moment. That that episode? Those sacrifices? Those conversations? The destruction of that wedding? Passing the fuck out? I’d do it again. Maybe not tomorrow. Or even next week. But I would. But only because you’d do it for me too, are we clear?

Stay tuned for the wing man version.