Not too long ago, I found myself standing face to face with a very handsome stranger at a Starbucks. It was a moment. I wanted to say “hi,” but I couldn’t.
Instead, I dropped my gaze, grabbed my coffee and silently hoped he’d say it first. He didn’t. I rushed out the door, and I’ve regretted not saying “hi” ever since.
Can you relate? Be honest. Are you head-down, scrolling on your phone whenever you sit in a coffee shop, stand in line or find yourself alone at a friend’s party?
Let’s face it: Our devices often feel like the death of real-world connection. People — especially members of Gen Z — tend to think small talk is cringe-worthy, so asking someone for their number can feel socially catastrophic. And yet, dating app fatigue is at an all-time high. If you’re single and tired of doom-scrolling or nervous about talking to strangers, how do you actually meet and connect?
Enter the “Triple H Challenge” from dating expert Benny Hart, which I learned about this past summer. In August, Hart launched the 30-day challenge: Say “hi,” “hey,” or “hello” to one stranger every day for a month. No fancy pickup lines — just practicing the basics of putting yourself out there and making organic, real-world connections.
Hart explained in a press release that people have lost the everyday ease of talking to strangers. The challenge gives participants a chance to reintroduce themselves to the world, break the patterns of swiping, build confidence and retrain their social muscles to meet new people more easily.

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Dr. Sally Homburger, a psychotherapist, backed this idea up: “When we engage with strangers, we experience novelty,” she said. “Nervousness, self-consciousness, excitement—they’re all different from how we feel around people we already know.”
“Our brains pick up social cues from body language and behavior, which teaches us how to respond and connect,” she continued. “Let’s say you finally say ‘hi’ to someone in your fitness class. They smile, ask a follow-up question, and your brain stores that memory as a positive association. Do that enough times, and your social confidence grows. It’s that simple.”
I decided to take on the challenge myself. As a single person with a love-hate relationship with dating apps, I noticed how often I default to my phone instead of connecting with the people around me. It’s a bad habit, and one that reinforces the feeling of being alone. So I committed to Hart’s 30-day challenge to see how it might change my life — including my dating life — for the better.
As I did the challenge, I wanted to understand why it felt so uncomfortable at first to say “hi” to a stranger – and not just people I found immensely attractive. It wasn’t because I found it cringey (I’m far too old to think that, let alone say the word out loud), but because my body didn’t always want to engage. My heart would race at times, or I’d feel like I wanted to jump out of my skin. Sometimes, I didn’t want to look someone in the eyes because it felt intrusive. Mostly, I just didn’t want to do it because it felt… weird.
Why does it feel so hard to say “hi” to a stranger?
According to Erica Schwartzberg, a licensed master social worker, it’s all tied to how our nervous system operates. “Culturally, we’ve become conditioned to equate approach with risk, especially in fast-paced, phone-absorbed environments. Social media has offered pseudo-connection while diminishing spontaneous in-person contact,” she explained.
“From a nervous system perspective, this means our window of tolerance for uncertainty or novelty in social settings has narrowed. Saying ‘hi’ to a stranger activates mild sympathetic arousal — like a flutter in the chest or tightness in the gut,” Schwartzberg said. “Without enough practice, the body interprets that activation as danger rather than excitement.”
Soon, I found that the more I said hello to strangers, the more comfortable I became doing it. Over time, it became almost reflexive. As I learned from Schwartzberg, that’s because my nervous system was getting used to it.
“From a somatic-relational lens, this process also activates the social engagement system, a branch of the vagus nerve,” she said. “When we smile, make eye contact, or match someone’s tone, we send cues of safety that invite co-regulation between two nervous systems.”

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As the days went on, I found it easier to smile, make eye contact and say “hi” to all sorts of strangers, from saying hello to a senior-aged woman in line at the coffee shop to striking up a little small talk with people I met while walking my neighbor’s dog. Doing so felt simple, natural, and even a little fun.
I started noticing the little rewards of connection: a smile, a follow-up question, a spark of shared energy. And yes, my nervous system learned to read those flutters in my body as a sign of excitement rather than danger.
Saying “hi” to a stranger — whether it was the barista at my coffee shop or someone in my apartment building’s elevator — became something I started looking forward to. I liked how it made me feel excited and connected, and I liked knowing it might brighten the other person’s day, too.
Homburger said this response makes sense because “when we engage in small social interactions, we experience pleasure through our dopamine reward pathways. Clients often tell me, ‘I need a quick dopamine hit.’ To me, that indicates they need to work on creating variety in their day, rather than just waiting for it to happen. If we can do this for ourselves, we will likely experience more satisfaction.”
Socially Awkward Exposure Therapy
Another key concept, she said, is exposure. The more we’re exposed to the new situations that scare us, the more we can “reduce that fear.”
“The trick is to start small — low-stakes interactions that create an optimal level of arousal without triggering full-on fight-or-flight responses,” she explained. “For example, sitting in a coffee shop with a book might feel brave enough, whereas going to a bar alone might feel overwhelming. Over time, these small exposures build confidence and help us experience more variety and connection in our lives.”
I think this is why it made sense for me to start small by saying “hi” to strangers and engaging with people I didn’t find particularly attractive (no offense to the lovely people I spoke to). The stakes didn’t feel so high when I noticed a cute guy in a fitness class and wanted to say hi. It’s not that I wasn’t nervous — because I definitely was — but having talked to enough strangers without it killing me, literally or figuratively, I knew I would survive that social interaction.
More than that, I trusted myself that it could even be fun thanks to my previous interactions. In short, I had rewired my old belief system: Approaching a stranger — even someone I found super hot — was no longer scary or cringe-worthy; it could feel completely normal, even — gasp! — enjoyable.
Homburger highlights how this ties into cognitive dissonance, which occurs when we hold conflicting beliefs about ourselves. “For example, you might think, ‘I don’t love meeting new people,’ yet find yourself spending an hour at a coffee shop reading a book instead of staying home alone. Over time, your brain works to resolve that contradiction, helping you form a new belief: that you are capable of these behaviors, and that taking small risks can lead to greater satisfaction.”
“Even fleeting connection feels good. Everyone likes to be met with a smile, and a tiny bit of kindness can go a long way.”
Schwartzberg added that there are other benefits to saying “hi” to strangers and stepping out of your comfort zone. Doing so can decrease baseline anxiety, strengthen self-trust and agency, rebuild the sense of belonging that modern isolation has eroded, she said, and train your nervous system to find safety in connection rather than defaulting to self-protection.
Saying hello or just smiling at someone are “forms of co-regulation,” she said. And if you’re a fan of TikTok therapy, you know co-regulation is a buzzword for a reason because it helps build trust and foster a sense of safety and connection between two people.
From a dating perspective, I found the challenge particularly helpful for trusting myself to approach someone attractive without fearing a negative outcome. I had a few nice chats with handsome men that left me feeling good, and while nothing romantic came of it, it reinforced that saying hi isn’t so scary, and the more you do it, the easier it becomes.
Beyond dating, saying “hi” to strangers made me feel more connected to my community and the world around me. While I don’t plan to greet every single person I meet — that’s extreme friendliness, even for a Canadian like me — I do appreciate that even fleeting connection feels good. Everyone likes to be met with a smile, and a tiny bit of kindness can go a long way.
It reminded me that in a world that often makes us feel alone, we’re all just seeking connection.
And hopefully next time I run into a handsome stranger at Starbucks, I won’t look down but instead smile, and maybe open the door to a romantic story that started with a simple “hello.”
