Hitting on people at a bar has proven to be unpleasantly difficult but I recently found out it’s even worse when the woman’s drunk. While playing shuffleboard with an attractive blonde at an idyllic establishment, our flirtatious banter was interrupted when her boyfriend arrived and planted a kiss on her lips. Sure, that’s a fail but one can’t let a happy couple diminish one’s ambition. There was a time when I thought being the bar-flirt was sleazy but even if that’s true, it’s a moot assertion – it’s survival dammit!
When a man approaches a woman, it’s obvious he’s hitting on her, roughly, 90% of the time. The mission – should he choose to accept it – is not to come off as a creep within the first 30 seconds and successfully convince her that he’s innocuously desirable by the end of the evening. I thought I found my next shuffleboard partner after seeing a woman sitting alone at a table studying her cell phone.
“Hey, you look bored. Want to play a game of shuffleboard?”
She peered up from her device and quizzically gazed at me as if my question was not only perplexing but unwarranted. After a brief moment, she asked, “Pff, what?”
I took this to mean she couldn’t hear me, so I grabbed a seat at the table with her and repeated myself. She smiled and politely declined. Gauging that she wasn’t put off from my sudden presence, I started a conversation with her that lasted for the next couple hours. Turns out she decided to drop by this bar on her way home from a party she had been to, and she was fairly drunk. Just to show you how ridiculous I can be, I thought that if I chatted with her long enough while she sobers up, she’d find that endearing and, possibly, go on a date with me. But like with any slipshod drunk person, the conversation lacked direction and purpose.
My friends left thinking that I was bound to get lucky that night, solely for the reason that I was still chatting with her at 2am. Maybe if I was someone else, it would have led to that but in my experience, it never does. Come to think of it, does it need to? Regardless, she gave me her number right before waving for a cab and disappearing into the disquieted early morning. I texted her so she’d have my number and name but got no reply. A couple days later, I sent this:
Unsurprisingly, we never went to brunch. After telling this story to my roommate, he said, “You know what your problem is? You should just be yourself and let the women come to you!” We sat in silence for 15 seconds then laughed and laughed.
-Single Guy in NYC
@SingleGuyInNYC
Single Guy in NYC 
To this day, I still haven’t had a guy come up to me at a bar.
Aww, I’d approach you! 🙂
You don’t even know what I look like. But thanks you made me feel better.
Aw man, bad ‘text game’ as they say. Don’t be apologetic, don’t even mention deleting when asking someone cute out for brunch! Play up more confidence, y’know. Fake it til you make it, may have to be that kind of thing, but really fake some more confidence…
Still, good for you trying. You’ll get better at all this.
Interesting thoughts Ray. I don’t agree that I was being apologetic but probably too innocuous with my proposal. There’s no need for my 3rd sentence but then again, if someone liked you, one would hope they’d find that endearing? Haha, who knows.
Hey, thought I’d chip in with the female take on this! I agree with Ray, mentioning the deleting is a little bit of an overcompensation. I know a couple of guys who kinda express the same sentiments as you in the dating world, and whilst they are genuinely decent and try their utmost to show they respect women and aren’t too smooth, they come across as stilted and look at women with those puppy dog eyes that unfortunately aren’t the same thing as bedroom eyes…fake confidence, it’s attractive to women! 🙂 Better luck next time!
This is why I love having a blog – these types of conversations are great. Agreed, 3rd sentence was unnecessary. I must have been feeling awfully benign that day. A good friend of mine never even poses questions to women he likes (eg, I’m having a party on Saturday, you should come). Cracks me up but never seems to work for me. I have confidence but a constant vigilance not to impose. Ah, there’s such a fine line b/t absolute ignorance and sheer confidence.
Ahh I’m afraid I agree! If I received that text my first thought would be that the sender wasn’t that bothered about seeing me and my second would be wondering if yeah, he was shy/nervous. Sadly neither quality makes for a good brunch partner… The best way to ask someone out is to be lighthearted and positive but also to the point 🙂
Cheers. This has been duly noted and I will gladly put this constructive criticism to use.
Thanks for your thoughts everyone!
I agree with the rest of the commenters! Less is more when it comes to texting. Next time a simple “It was nice meeting you. How about brunch?” would be better. Don’t even pick a date. Let her decide and respond first. Work out details later.
Argh, I definitely should have gone with that. I appreciate the feedback as I strive to fine tune to the single life. On to the next fail then.
Thanks for reading!