Deciding to Flirt with a Stranger in Public

girl flirting wink flirt

I’ve been recently contemplating whether or not I should flirt with a stranger in public. You know, like people used to do before online dating and social media existed; approaching someone out of the blue in a way that doesn’t allow me to shield myself with a phone screen. While this type of flirtation style still happens today, it’s not as common as it used to be. Personally, there has been very, very few times where this has happened to me, (in a positive way) and I know the same is true for many of my millennial friends. Despite there not being a big culture around this flirtation style anymore, sometimes it’s the only option to get a cute stranger’s attention, so that brings us back to me, still contemplating whether or not I should do it.

I have the confidence to do a lot of things, but flirting with a stranger in public is not one of them. Oh, I’m fine with asking a person on the street where she got her shirt from, or yelling at a racist at a protest, but put me in a public setting, with a cute person I don’t know and damn, I’m done for. I get quickly distracted from what I’m doing, stare at them to see if they notice me and blush hard when I realize how creepy I’m being.

I’ve always been this way. In high school, I saw plenty of cute boys that I didn’t even dare to approach because I had no rapport with them to lean on. I felt like I needed an excuse to talk to them, a reason so I could gauge if they actually had any interest in me. I would find subtle ways to try to make friends with people before I determined whether they wanted to engage in a consensual flirt. During that period of my life, I was worried that I wasn’t attractive enough for people to want to flirt with me; that my size enabled people from finding me desirable. My solution was to stay quiet and wait for the crushes to approach me, but that technique didn’t do me many favors and resulted in a lot of missed opportunities.

This lack-of-flirting method is still something I struggle with, even though I’m a much more confident person that I was before University. Lucky for me, dating apps exist, so I don’t have to make a mess of myself attempting to determine whether someone is into me. These don’t help me IRL though, I still sit back when I see someone cute and write off random street flirts as losses because I’m too much of a chicken to make a move.

However, recent events have made me reconsider my passive flirting nature. As I’m moving to a new part of my city soon, I’ve forced myself to switch my regular coffee shop to one closer to my new place. The iced mochas are delicious, the Hello Dolly’s divine, and as if my experience couldn’t be any sweeter, there’s another regular who I have quite the crush on. They sit facing at a table facing the door, working away on their laptop. Every day when I come in, they look up from their laptop, we make eye contact for approximately three seconds and then we both look away as I stand in line to order.

I can’t help but think our brief eye contact is a sign that I should eventually find a way to start a conversation with them. But, despite our daily encounters, I still haven’t found a casual opportunity to make small talk and put my flirty-feelers out. Is my crush making eye contact with every patron who comes in, or if I’m an anomaly? I don’t even know if they’re trying to make flirty eye contact; it could be my rose-tinted glasses tricking me into thinking we’re sharing a moment.

So I have two options: awkwardly continue to make eye contact every day until we naturally converse OR approach them myself with a non-invasive compliment to let them know I’m interested. This could be a simple decision, but my passive-ass self is overthinking it. Even if this person is giving me flirty eyes back, do they want to be approached? Am I just a distant, looking-only being, who’s to be left behind in the coffee shop without additional pursuit? I don’t know, and there’s no way of knowing without reverting to the second option: actually talking to them. Which, despite a nervous voice in my head screaming “Nooooo..”, I’ve decided to do.

I’m a Yes girl; I do things for the story and I’m always chasing an adventure. With curiosity and courage being apart of my personality, it’s a common occurrence for me to purposely push myself out of my comfort zone once I identify a fear or hesitancy. So here I am, deciding I’m going to flirt with this regular patron in my new coffee shop.

I’ve mulled over how I should approach them for awhile. I need an advance that is the perfect mix of forward and casual. Nothing too aggressive, and not an introduction that will require this person to make a decision too quickly (I myself tend to agree to things without thinking if I’m surprised by an advance.) I want it to be clear that I’m flirting but leave them with room to decide whether or not they want to flirt back. With my intent in mind, I crafted a one-liner that I plan on saying to this hot human:

“Hey! I just wanted to let you know, I think you’re really cute.”

And that’s it. To the point, easy to spit out in one nervous go, and open ended enough to allow for a variety of responses from the complimentee. The one-liner gives the receiver options to say nothing at all, an easy ‘Thank you’, or give a compliment back. It’s a statement, so even if they do happen to not reply, I can walk away easily without needing an answer (in which case, I can be happy with the fact that I had the courage to upfront and honest.) We shall see how it goes.

Deciding to flirt with a stranger outside of the internet was a bit of a complicated decision-making process. I’m a planner at heart, and I’d rather flirt in the most respectful way possible, so it did take some time for me to come to a verdict that worked for me. While it won’t matter whether this person wants to flirt back or not, at least I have the courage to pursue any other IRL flirtmances.

Have you ever approached a stranger in public to flirt with them? How did it go? Has someone ever tried to flirt with you in public? How did it make you feel?

*Not every person may be open to being approached with this line. Please be aware of social cues and context when deciding to flirt with someone.

2 Replies to “Deciding to Flirt with a Stranger in Public”

  1. Suz,
    I think that this is a great thing to start bringing back! By being able to hide behind the screen, society as a whole has become awkward and anxious in these situations. not just the millennials, but I feel like we got the brunt of it. How do you fix it? You practice! Go for it! And I hope your article meets the eyes of many, to give them the courage to do it too. Good luck! I’d flirt with you ANY day!
    I just hope that the college friend (I rekindled with) that I had coffee with the other night was catching my subtle flirt-bombs. …so I get you.

  2. It has been years since I had to flirt in public. But this usu. worked, and gave the flirted with all the options. Have a calling card made, ala Jane Austin, with whatever contact info you want to give up on it. I am going to “x” on whatever day, it would be nice to see you there. Anyway I felt that it had some charm.

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