How To Ask Someone Out Without Being Creepy

Updated June 3rd, 2019

I’m so scared of looking creepy I won’t even ask you out.

Huh, what?

Dating is Awkward

I was at a bar in Goa recently doing what middle-class millennials do when they’re trying to cling on to their youth.

Having some drinks, wearing my cool Rainbow sandals that I got from California and chilling with some friends.  

And since I’m a fairly normal dude with an ok life on paper…by friends I mean 8 guys and 2 of their wives.  And by chilling, I mean pretending to enjoy the techno/psytrance/electronica or whatever it’s called these days while some douchey Russian bro tripping next to me reminds me of my bad life choices.

You get the idea.

As the evening is in full swing, I notice a group of four girls checking me out from the corner of my eye.

Now I’m no Brad Pitt and nothing to swoon about (although I did check to see if Brad was perhaps behind me), but I am fairly aware of my surroundings and have an ok level of confidence you require by a certain age.

I’m not the prize of the show but I’m not hideous, and when a group of attractive females are eye humping you, you’re mind figures out a game plan.

I started thinking maybe there’s a small chance I know one of them, or perhaps they know me, or hey, maybe, just maybe, this is what Goa is really all about. (Ahhhhhh yeah…….it’s going down).

So I did what any of us would have done in that situation.

NOTHING.

Now I would love to start my lecture to you about how bars are a waste of time, but that’s not where I’m going yet.

Oh, how I wish it was.

You see while I noticed the ladies and took a sip of my drink while awkwardly making eye contact (which by the way, please never do while sipping), my friends did also.

So the peer pressure was on, and since we exchanged a few smiles and I was feeling in my zone, I went for it.

CONFIDENCE LEVEL: MR. PITT

Dating is not the movies

Lowered the drink near pocket level to avoid spillage (cue Eminem music), waited for a gap in the crowd and began the swag walk over.  

Step by step, playing out each quick option in my head.

“Hey, hows it going? You girls like Goa?”

You girls like Goa? WTF?

Easy enough I thought, but very generic.

But screw it, eye contact made and smiles exchanged, this would be easy enough to chat for a bit, impress the friends staring from their safe zone and then say bye and walk back, number in hand with the confidence of Oceans 11.

So I walk up and say “Hey Ladies, how are you?” and wait for the glory to begin.

They take a look at me, giggle, and turn around.

Confidence Level: Zero.

Dealing with Rejection is Normal.

I’ve been rejected before, and I’ve done the same to others for probably the same reasons. (e.g. I don’t find you attractive but I got to make something else up). Rejection I can handle, and it’s completely normal to be on both sides.

But the reason I write about this one now is that it sort of triggered off so many mixed emotions in my head.

I really have no recollection of what those girls looked like, but I clearly remember everything else.

Walking back embarrassed, laughing about it as my friends commended me on the effort, and then giggling to myself in the plane like a psycho as I thought of this blog.

But the main thought, the main confusion and main embarrassment in the moment was “What exactly did I miss?”  

Did I take too long to approach them, and somehow lose their interest by the time I cozied on over?

Was I too generic in how I said Hello? I mean clearly these girls are savants of passionate romantic authors like Milan Kundera (Unbearable Lightness anyone?) and introductions required much more than a simple “hi.”

Or am I really having an epiphany about bar culture thinking I was about to meet the love of my life at 3 AM in a crowded disco in the middle of Goa during Biker Week?

The answer to all of those questions is yes. And no. But more importantly, who gives a shit?

If you’re confused, well you’re supposed to be.

Because that’s what growing up in pub/club culture is really all about.

Confusion.  Misaligned expectations.  And whole bunch of WTF moments.

None of us are really there for the music or good conversation, although we all enjoy being around people and knowing we picked the right place for the evening because “that’s where everyone else is.”  So we each stumble through these nights acting/behaving in a certain fashion that creates a series of frustrating experiences like the one outlined above. The girls probably don’t care about dancing but do enjoy the selfies and having a night out, and the guys could give one shit about the DJ but are hoping to at least massage their egos as the night progresses.

Either way, this presents a huge set of problems for you and me.

Of the hundreds of nights out I’ve had with friends, I’ve probably spent 80/100 at a bar/restaurant/club. And out of the hundreds of weddings I’ve been to, I think 1/100 of those couples actually met as strangers in the night at a local pub.

The same is true for friendships, in that I don’t think I have a single close friend I initially met over a drink.

As a result, for a single bachelor or bachelorette, things get interesting with time.

When you’re 22 this world is exciting and full of promise.

You walk around full of confidence in whiskey form shoving your groin into anything that moves, thinking the girl will turn around and say “Oh my, what a gentleman you are.

Let’s go back to your hostel, I don’t even mind if it’s non-AC.”

When you’re 25, the hostel becomes a hotel (or your own apartment), and the cycle continues.

As you cross 30, full of disposable income but still trying to fill your social calendar, it becomes a bit easier to spot the gaps.

You realize many roads lead to the same place and you might be taking the one in need of some major repairs.

Guys and girls are both looking to meet people, date, travel, have shared experiences and live up their youth. You can do all these things but straying from the herd once in a while might be the way to do it.

We complain about movies and skip the bad ones.

We complain about government and involve ourselves as required.

With the modern dating/bar-hopping scene, try to make your own decisions as well.  

Pubs are a great place to spend time with friends, but not an ideal place to make new ones.

Plato

We should complain about those too.

If I sound like some jaded loner who is just burned out with the status quo, that’s ok. I’d rather it be me than you. But as someone who has done great some months and terrible others on the social front, one thing I’ve realized is the system generally forces you to be something you’re not.

I grew up hearing the phrase “Nice guys finish last” even though that’s all I ever wanted to be.  

I like helping my friends and it brings me joy to see them happy.  

If a girl texts me and my phone is nearby, God forbid I reply right away.  (Wait two days? Dude, I got this slick haircut today and she needs to SEE IT NOW).  

I also was a platinum member with the hotel brand the JW Friend Zone. But in my own personal experiences, only when I started to ignore the opposite sex did I find them no longer ignoring me.

I couldn’t entirely be myself cause the friend zone got boring, but I couldn’t come on too strong because that wasn’t who I was and there’s a very thin line between cool and creepy.  

And frankly, most of us have no idea when we cross it.  

I would love to ask the cute girl at Starbucks if she would like to get a coffee (Whoa…if you make a coffee date at a coffee shop did it just happen?) the way I hear it’s supposed to be done.

I’d love to swoon you off your feet on the dance floor or over tequila shots the way MTV showed me.  

But honestly, all of that seems like a paradox these days.  Men and women want a partner who’s planned yet spontaneous, sweet but has an edge, and competitive yet relaxed.

HUH?

CONCLUSION

When you play by the book you’re unoriginal, and when you try all the cool shit you realize the book is fiction.

Dave Chappelle once famously said that “Chivalry is dead and women Killed it.”

While the crowd immediately recognizes the joke and bursts out in applause, there is an obvious recognition of truth that cuts both ways for men AND women.

We live in a time where both genders complain about being single even though (technically) it’s never been easier to meet someone.  

Technology killed our social interactions, we have dwindling attention spans, yada yada.  

But when you’re spending your days learning to be yourself and then spending your evenings trying to be someone else, at which point do you step back for a laugh to realize how absurd it’s all become?  

There was a time you could walk up to someone, smile, and tell them something polite.  In fact, as far as I remember, that was what you were supposed to do. When that changed, I have no idea.

But if you can’t even do that anymore, what are you supposed to do?

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