I Challenged Myself To Flirt With People IRL & Learned I Need To Practice More

I'm perfectly comfortable sending a flirty message online via dating apps or iMessage, or after an already-established connection is made, but putting myself out there with a likely chance of humiliation? Yeah, not my cup of tea. I've never been one to just approach people I find cute out of the blue and say something gutsy – I'd rather talk to them for a reason like saying, "Can I pet your dog?" so I have somewhere to start. When my editor challenged me to flirt with strangers IRL, I knew this article was tailor-made for me. I had zero idea how to flirt with people in real life. Are you supposed to just go right up to someone and say something? What do you even say?

I figured it would make most sense to test out my flirting skills in a place where I wouldn't know anyone. It seemed easier to put myself out there when the risk would be lower — I'd never see these people again, most likely. So, I decided I'd do my experiment while on a weekend trip in Durham, North Carolina. I was staying at the hotel Unscripted Durham — it's a hotel built in the 1960s that's in the center of downtown, with eccentric blue exteriors, and a young and hip vibe perfect for anyone wanting to be right in the middle of the Durham action.

While waiting for my plane from Philadelphia, I sat at the gate and read Josh Radnor’s cleverly titled newsletter “Museletter." "I've never not found gold on the other side of risk," he said in the most recent blast. Now, at that point, I wasn't expecting flirting to work out well on my first attempt, but I knew it couldn't be as bad as I feared it would be. Plus, there was a chance something good could come out of it. But it was hard to see that happening with my nerves running high.

So, why was I so scared? Well, putting myself out there IRL has heavier consequences than it does on the internet. If I say "hi" first to someone or double-tap all of their latest Instagram pictures, what’s the worst that can happen when they reject me? I unmatch them on the dating app? Unfollow their Insta if they don’t like my posts back? In real life, going up to someone and flirting has consequences I can see and experience if the other person isn’t interested. They’ll be able to read my embarrassment. Maybe others will notice the interaction and stare at me while I walk away in shame.

Making myself vulnerable, exposing my feelings and letting another person know I'm into them... well, it’s terrifying. This all to say, it’s clear I don’t have much experience approaching people with the intention of flirting with them. Sure I’ve flirted with strangers online and IRL before, but I don’t recall ever taking the initiative to flirt first in person. Usually I have a few signs they are into me already. So when the opportunity came to try this, to force myself into expanding my horizons? I decided to try it.

For my first foray into initiating flirtation, I smiled at the cute pilot as I exited the plane in North Carolina and said, "Thank you." I knew I wanted to say something to him leaving the plane from the moment I boarded it, and figured showing thanks for getting me there safely would work. Now, I know that's benign for you heavy-hitter flirters out there, but I think slipping someone my number will take a bit more practice to harness the confidence for that sort of thing. Maybe in a few weeks. Or months.

While waiting for an Uber, I locked eyes with a cute guy wearing glasses. I was suffering so much tomato face I didn’t know what to do. So, I retreated to the comforting safety net of my iPhone, ashamed I didn't do anything about meeting his gaze. I wished I had the courage to start a conversation, but I resolved I'd try to be braver the next time around.

The next morning, I meandered around Durham. After a recommendation from an employee at Dolly's Vintage, I walked over to the Durham Farmers' Market.

There were vendors selling produce, coffee, cheese, and art. I think it's some new law of the universe that every cheese store employee I meet is cute and makes me flustered. (This has happened multiple times at a market in the Philly suburbs. It's fine.) I nervously grabbed two free cheese samples and averted eye contact because I'm me and awfully embarrassing, so I kept on walking after that. I know asking about the cheddar I sampled could've been a decent conversation-starter, but it was crowded, and he was helping other people, and I just felt uncomfortable with trying to force something in that moment.

Later in the day, I popped into Letters Bookshop, a Durham independent bookstore. The bookstore employee was very cute — curly, short hair, taller than me, and wearing glasses. We were alone in the store. He asked if I needed help and at first, I said I was just browsing.

But then I realized maybe I should say something to actually start a conversation and I was looking for a particular book, anyway.

I asked him if they had To All the Boys I’ve Loved Before in stock. He went to the computer to search for the book, and I quickly thought to add, "Oh I’m sure everyone wants to get it now, because of the movie."

He replied that he doesn’t get the chance to see movies often.

I said, "Well, it’s on Netflix, so you can chill and watch it whenever. They’re bringing the rom-com back, you know?"

He smiled and nodded. Go me, I guess?

I then walked around the store for a bit to see what other books they had (no luck for the new Netflix hit), bought two books on sale, smiled, and said, "Thank you." At that point, I felt discouraged — what more could I do without feeling so wildly uncomfortable? I could've complimented his smile, I suppose, but that felt so obvious to me. Of course he had a nice smile. But me saying that... it felt too vulnerable.

I thought maybe my subtlety may have been too subtle. It could read as friendliness if there's no interest, and it's the kind of flirtation that allows for natural conversation and a smooth getaway. I was only asking for a book in a bookshop. I was only smiling at people whose eye contact I met.

In the hotel elevator on my way back to my room, a a guy straight up was gawking at me. I thought, is this what flirting is supposed to be? Just staring at someone? Because honestly, it made me very uncomfortable and simultaneously flattered. But I'm not quite sure I like that approach, either.

My journey continued later that night after dinner, when I stopped at a local ice cream shop, The Parlour, for dessert.

I told the ice cream cashier that I liked her tattoos in at attempt to be flirtatious. There were lady bugs and flowers across her forearm. She said, "Thank you, I appreciate it." I smiled back and ate my ice cream, then wondered if this experiment was a total failure on my end.

On the flight home, I reflected on how the experiment went. No, I didn't give anyone my number or ask them out, which I thought would be the goal of this experiment, but I did dare myself to be a little more social and flirty with those I found attractive. I realized it's OK if approaching someone in public with a bold move isn't ever going to be something I'm fully comfortable with. That doesn't mean I'll never do it — it just may take some time.

As for my future flirtations, I will keep trying to be braver in person. I've always been willing to say what I feel online. But maybe, one day, I'll get to that same point IRL, too.

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