Should you ask out a stranger

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I’ve always told myself and other people that I want to ask out a stranger more often. Not randomly and sporadically of course, it’s not like I want to treat every woman on my morning train like They’re on a yo-sushi conveyor belt. Plucking out the tasty colourful ones.

Sometimes I hear through the whispers of my female friends and the nonsensical chants of social media that some women just want a natural encounter rather than a digital profile to swipe and an onslaught of text messages.

My response to this is usually agreement with a touch of personal truth. Asking people out in public is sweat-inducing, scary shit.

Why ask out a stranger in public

ask out a stranger

I like to think that asking someone out in public is one of the coolest ways to start a romance or a potential public trainwreck. Doing it successfully sometimes depends on correct timing, their mood, the way you approach, what color shirt you’re wearing, how eager you are, how eager you aren’t… I mean really. It’s easier to just think about doing it than worry about if you’re going to succeed.

There’s a rush you get from performing the task even if you don’t get the result you want. And there’s a buzz you might give the person you asked, even if they say no. It’s a bit more personable and definitely breaks away from the very common “How’s your day going” opener littered across dating apps.

If done respectfully, the other person may be so taken aback and flattered by the perhaps rare occurrence that they’ll give you their number without even figuring out if they want to date you or not. Which is kinda part of the natural beauty of it.

Ask out a stranger – The first time

The first time I asked a stranger for her number I was somewhere in between a teenager and budding adult. Most lunchtimes I would see this straight-haired Greek girl at my local boots. She was one of those people who seemed like life gave them a happy pill every morning. We would share a quick 20-second conversation before I went back to my part-time job to literally inhale my lunch.

A couple of weeks went by where I hadn’t visited said local boots and when I decided to peer my head back in again, there she was. I almost remember stalling just so she would be the one to serve me.

“You’re late she said”

I looked up for a moment a bit shaken at the boldness of her comment.

“You’re hair’s different”

I reply like I plucked the first topic I could think of out of the air. On this occasion, it was bigger and very curly. She seemed amused and smiled like I had passed a test of character.

Later that week we ended up walking down the same road and she mentioned she needed books for studying. I worked in Waterstones at that time so I decided to spark a trade, her number for some study books. I got the number, she never got the books.

Not exactly the most straight forward example, but hey I was young and slightly less clueless than I am now. I had lots of time to become a comfortable fixture in her day to day and luckily she was quite up for a chat when I needed food in my mouth.

And I didn’t really ask her out so much as acquiring her number through the pretense of book buying.

Why we don’t ask out a stranger

Did I mention it’s scary!! Asking someone out in public can be tricky, especially in a place like London. A city full of anti-social travelers who seem to have better things on their minds than to have their personal space pierced by a request for their magic digits. Heads wrapped in wires and ears full of any distraction to take them away from the reality 2 inches from their bodies. Eyes focused so tightly on the devices meant to bring us together, faces that have been nurtured on four hours of sleep and would willingly bite your finger off if it’s in edible reach. I’ve basically just described myself on most Monday mornings.

ask out a stranger

Not to mention it’s way easier to pull out your phone and swipe right… or left? You’ve probably seen it on tv shows which probably got the idea from someone’s real experience. Guy sees girl, alone in a scant bar, like a retired James Bond he steals a recorded look at her through the slithered view between his beer glass and fingers. He proceeds to load his chosen dating app and frantically swiping to find her face. It’s the easiest way to make an initial connection in our decade. Have you ever done this?

Do you frantically swipe in bars/clubs?

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Lastly, the brunt of the pressure tends to sit with the male side of our race. Not that women don’t also give it a try, but their talents seem more focused around heavy-handed luring than the actual asking. Even on dating apps, I’m not sure if I’ve ever been asked out by a girl, maybe once.

Ask out a stranger – The last time

I’ve always been quite a promoter of people rocking up to randoms and “shooting their shot” as my brother would say. So whenever I sense a ripe moment to “shoot” I do my very best to charge through my mental barriers and just do it.

It’s a lot like jumping off a diving board, the build-up feels like a soft clamp pushing against your chest, restricting your logic and pushing out a plethora of consequences that only exist in your mind. I try to recognise that feeling as what it is and jump.

While catching up with a friend in a casual steak restaurant. I noticed we had a cute dirty blonde waitress maneuvering round our table, taking orders while delivering booze and sustenance. She had a wide smile when she took our order, the kind of grin that looked like she needed it to support her cheeks.

I found her attractive and maybe it was the wine loosening the locks of inhibition in my brain, but a small idea started to grow and bear fruit in my mind. I should ask for her number.

There might be unspoken rules about asking waitresses for their number, perhaps it’s frowned upon. Like customers assuming the women in the restaurant are also part of the menu or something.

Nevertheless, I figured the worse she could do was say no, it was too late for her to spit on my steak or something.

We asked for the bill and luckily she came to take our payment. Here was my chance, I had half a bottle of wine in me for encouragement, here we go.

“Sorry but could I ask you something”

As usual, I start with an apology. The British way.

“Yeah, sure”

She responds, looking at me as she rips the receipt from the portable card machine.

“Are you seeing anyone at the moment?”

Her polite smile becomes amused.

“No, I’m not”

“Would you like to be?”

The words leave my mouth before I can process them. Did I just say that? My friend recoils in laughter. The waitress responds in kind.

“Yes I would”

“Could I get your number?”

“Yeah okay”

Score!! At this point, whatever smooth soul inhabiting my body dusts it’s hands and leaves me to fend for myself. I fumble around trying to unlock my phone before she changes her mind.

“I’ll put my number on your receipt”

She assists

“Ah… tha.. thanks”

I leave with her number and her name on the receipt. Shoulders strong and head high like I’ve just been promised the lottery.

In this situation, I consider myself lucky. What I said was quite cocky and could have easily backfired. The most conversation we had was a very short discussion about what kind of sauce I wanted on my steak. Not to mention my dinner friend was a very attractive lady and who knew what our relationship was.

Maybe I caught her off guard, maybe she found me funny and confident rather cocky and creepy and maybe having a female companion made me seem more trustworthy and eligible.

Which girl do you think I "Got"?

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Ask out a stranger – The reality

ask out a stranger

It is fun and electrifying to breakthrough you’re mental bonds and achieves something you’ve never done. Especially when the end result depends on the answer from another. But it is important to know that not every attempt leads to success and not every success to a satisfying and positive result.

From the two examples I gave, the first led to one of the longest relationships I’ve ever had, and the second led to 3 days of silence and then a polite “not ready to date” text response.

On Reddit, there’re a lot of threads about people “shooting their shot” which is basically going up to someone and asking them out. It’s praised, glorified and encouraged. Though there are also other threads and opinions discouraging that very process. That just asking someone out is creepy and wrong, especially when it’s done for clout, like giving a wad of cash to a homeless person and filming it for social media (gosh that makes me feel weird).

I’ve actually only ever dated one person from the people I’ve asked out naturally, but considering I’ve only asked like 6 people (that I can remember) and swiped right on more faces than I’ve eaten sweet potato fries, my results aren’t half bad. It just seems to take a considerable amount of mental energy to actually do it.

On good old Reddit, there’re a lot of threads about people “shooting their shot” which is basically going up to someone and asking them out. It’s praised, glorified and encouraged. Though there are also other threads and opinions discouraging that very process. That just asking someone out is creepy and wrong, especially when it’s done for clout, like giving a wad of cash to a homeless person and filming it for social media… gosh that makes me feel weird.

The opinion is that you should get to know the person first before just asking for their number. Asking them a bit about themselves or striking a conversation before pulling the trigger. I agree but there aren’t many situations where you can have a chat with a stranger before asking them for their digits.

Should you ask out a stranger

Yes!! It’s tough to try and find someone outside of the now popular dating apps. But drawing up the courage to ask out a stranger in public is a refreshing change that gets easier the more you do it. Humorously I was actually asked out in public a while back. At least I think he was asking me out. It’s a story I’ve already written in The Guilt Trip. So maybe “shoot your shot” sometime and see how you feel.

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