The Horrible Wingwoman (Girl Fail #6)

Upon my vindictive return to the same bar as my last fail, Girl Fail #5, my friend Sherry offered to be my wing-woman.

“Just point to a girl and we’ll go over,” she decided reassuringly.

After clarifying with her that pointing at a complete stranger is not the ideal first impression, we made a plan – although contrived and arguably not so ideal as well.

The plan: After selecting a group of girls, she would infiltrate the enemy base, deploy a cunning compliment targeted at one of the girls and just when all hope is lost, I would parachute down, eliminate the threat (Sherry), and hoist everyone to safety with my irresistible charm.

What actually happened: Sherry suggested a group of people behind me, to which I asked, “Which group?”

Extending her arm, she answered “That gro-”

“Don’t point!”

“I’m going to compliment her blouse or something.”

“Whose blouse?” I exclaimed.

And with that she walked right past the group of people I assumed we were talking about and right up to a group of three girls by the back of the bar. ‘The hell with it,’ I commanded internally. I walked over to them, parachuted down, and overhearing Sherry deploy her compliment, assailed her with the following: “You causing trouble over here?” My timing was flawless but my delivery was horrendous.

As if acting on a poorly rehearsed cue, Sherry gestured to me with both hands and, like a circus ringmaster introducing the next act, announced “Well! Let me introduce you to Single Guy In NYC.” (Keep in mind that this was only her second sentence to these strangers.) Mayday, mayday! Abort!

Struggling to recover my balance, not to mention my abating confidence, I peered at the three girls that were addressed and made note of their justifiably displeased countenances.  Turning back to Sherry in an effort to smooth over this erratic transition, I was surprised to see she wasn’t there. Ten feet away from us, fleeing the scene, was Sherry displaying a smile of wholly satisfaction at what she conceived as a job well done.

Bracing for a diatribe from the three girls, I looked at the one that caught my eye and said the first thing that came to mind: “Did you come here for the game?” nodding to the TV overhead. Yes, it was rude of me to address only one of them but I was outnumbered and getting the notion that my efforts would be futile anyway. Instead, I was greeted with a cordial smile and a sincere response from her. Fortunately, her two friends just contemptuously glared at me and turned around. And just like that, we began a conversation that lasted, believe it or not, for two hours.

She was smart, funny, cute as all hell (is hell supposed to be adorable?), and charismatic. Not only that but we lived within 20 minutes of each other (distance is everything in NYC – a Bronx and Brooklyn couple is basically a long distance relationship), listened to the same music, enjoyed the same cafes and bakeries, and both loved Europe. I haven’t felt so much at ease conversing with a stranger for a long, long time. After my last relationship, I’ve grown extremely reluctant to fall in love again but it was already apparent that love would only come naturally if this conversation led to something more serious.

“And do you come here often?” she asked earnestly.

“Wow, worst pick up line ever! I expected more from you.”

Laughing out loud, she remarked “Oh sorry, I honestly didn’t mean it like that. Let me try again.” She took a step back with one foot, dropped her lush hair down to her shoulders, gazed at me salaciously and in a seductive tone asked, “So,” pausing briefly, “you come here often?”

Forget what I said before, I was already in love. Well, as much as one can be the first time one meets someone new. We were so caught up in our flirtatious interactions that we didn’t bother ordering another drink for the rest of the night. Needless to say, I left with her number and was soaring high on cloud nine. I texted her the next night and this was our conversation:

Text Single Guy in NYC

I’ll give you a second to reread her last sentence. Don’t bother searching Google or asking friends for insight. What she said was pure rubbish meant to kill the conversation. The question is why.

She didn’t reply, so I knew I had to think of something witty. After 20 minutes, I responded.

Me:  Are you filling out a mad lib at the moment?

Her:  Haha no just tired  🙂

Me:  Fair enough. Don’t operate any heavy machinery in the meantime

Testing my luck the next day was also fruitless. All I wanted was to have a short conversation through text before asking her out. After our second conversation (if you can even call it that) dissolved into nothingness, I agreed to go with the Hail Mary and ask her out, even though she hadn’t responded to me in days.

Me:  Hey, what are you up to this weekend? Texting is overrated and I know this great brunch place in Chelsea

I never heard from her again. I suppose she had other options and, more importantly, nights like ours were more of a banality to her than to me. Truth be told, since this Girl Fail, I haven’t been able to muster the courage to meet anyone new. It’s now been close to three months and I feel as though we broke up without having dated. There must be something wrong with my head. What do you think?

-Single Guy in NYC
@SingleGuyInNYC

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9 thoughts on “The Horrible Wingwoman (Girl Fail #6)

  1. Aww! I had high hopes reading this. Sounds like you both really hit it off.
    Much like my date with “the blogger” (as mentioned in my “I’ve been played” post), it looks like we’ll never know why they lost interest so quickly. It still amazes me how some people can’t even muster up a “thanks, but no thanks” response. Personally, I’d prefer that to no response at all.
    On to the next one Single Guy NYC 🙂

    • Agreed! And each and every time I have a connection with someone, I assume we’ll at least go on one date. Instead she’s got to put plates on her bed and such. I have two more failures to write up this week to follow up with this one too.

      #Chagrined 🙂

  2. Wow, what a story! I have seen several YouTube videos about Wingmen and Wingwomen but your story truly made me smile! The text message was a little awkward, and maybe that’s the new way people blow one another off is by stating something extremely odd hoping you lose interest! This dating scene is for the birds! Better luck next time…without a Sherry though!

    • Sherry’s been benched.

      Maybe this is the new wave of rejection and the less fortunate missed the memo. I honestly could not think up of a more haphazard combination of words in response to such a simple, harmless question.

      Glad to make you smile though 🙂

  3. Hilarious, but I probably shouldn’t laugh at what eventually let to your misery. It was kinda funny in the beginning though…
    I think I’d have stopped texting after she sent you a text containing the words ‘bed’ and ‘bang’ in the same sentence, that didn’t include you. Just a thought.
    You know by now that I’m going to tell you what I think (until you block me from your blog or something) but I’d prefer a call over a text as an initial contact. Maybe I’m just old (fashioned! I meant old fashioned…!!!) but it’s more personal and seems to be more sincere. BUT, I’m just silly like that.
    : )
    better luck next time!

  4. Loving the male perspective, I must say. That text is beyond bizarre- I’m afraid to try to make sense of it else my head explode. You want my guess? She’s attached, but enjoyed the “harmless” flirtation and attention. Gave you her number because it’s easier than refusing. Yes girls do that, yes it’s shitty. Seems like you’re affirming the hunch that meeting some one is harder than ever these days. It feels like online dating has taken over- I rarely get chatted up by guys any more (I’ve convinced myself it’s not just me). All the kudos in the world for trying.

    • You’re probably right. I’m glad you’re enjoying a guy’s point of view. It shouldn’t be a secret that approaching people in a social setting is challenging and, sometimes, unnecessarily arduous. Regardless whether one is shy or social, we all trip on our words (especially when alcohol’s involved).

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