Last year, at a party, I bumped into a handsome guy who I had met the month before at a yoga event. After exchanging pleasantries at the bar, he said, “You look very nice today.” I said thanks and turned my back to him to continue speaking to my friend who was next to me, listening in on our conversation.
“What are you doing? He is obviously your type and he was trying to flirt with you!” she said. I was so confused. I didn’t pick up on any signals and assumed it was just polite conversation.
I don’t know how to flirt, and I can rarely tell if someone is flirting with me—and I’m not alone. Recently, I attended an online class on being single and navigating dating in the current climate. The therapy group had people from all over the world, some in their 20s and some in their 30s or 40s.
Two topics stayed consistent regardless of age or geography. The first was that people were fed up with the fact that no one approaches each other or makes the first move. The second was that no one knows how to do so themselves
Today, many daters are fluent in texting but far less comfortable with ambiguity, rejection, and face-to-face social risks. Now, relationship therapists, psychologists, and cultural commentators warn we are at risk of losing the fine art of flirting.
Digital culture can take part of the blame. “We’re living in a culture that is more digitally connected than ever before, and many people are getting less used to having everyday spontaneous face-to-face interactions,” says Victoria Wren, a therapist based in the U.K.
People spend lots of their time communicating through apps, direct messages, or video chats. All of these digital platforms give us control over what we say, how long we take to respond, and how vulnerable or honest we choose to be.
The stakes feel a lot higher in the tangible world. “If we feel like we’ve overshared or said something we did not mean to say, we have the opportunity to just edit or unsend a text now,” Wren says. “Approaching someone in real life requires risking rejection, taking courage, and accepting that things might not work out as hoped.”
But not everyone feels comfortable taking that risk.
Previous generations practiced talking to strangers while waiting in line, making conversation in bars, reading body language, and navigating awkwardness because there was no digital alternative. Today, the reality is much different. Rather than engaging with the people around me, my phone often fills the gap in my day. When a friend is running late for lunch, for example, I scroll aimlessly, answering emails or texts.
Often, existing in the modern physical world can feel like a standoff. Recently, in a restaurant with my friends, I made a point of smiling and looking at a guy on the other side of the room. He felt my eye contact and did the same, but neither of us approached the other. I left frustrated.
Perhaps part of this standoff is that many of us have learned to fear rejection. During my group therapy class, several men in the group told us about their terrible experiences of approaching women and being rejected in humiliating ways. One guy said he asked a woman about the book she was reading and she just loudly screamed, “Go away!” Going forward, many assume the same experience will happen again if they approach someone, so they simply don’t.
Our therapist, Stephanie Beebe, reminded us that our generation didn’t really learn interpersonal skills. She has been married to her husband for more than three decades and said her generation had to rely on exceptional interpersonal skills in everyday life because you couldn’t hide behind a screen. If you wanted to ask someone out, flirt, apologize, resolve conflict, or simply make conversation, you had to do it face-to-face.
Today, many people no longer have the same opportunities to develop the interpersonal skills that flirting requires. And while many people say they want to meet a partner organically instead of through dating apps, many daters also express fears of rejection and an unwillingness to make the first move.
That made me wonder whether the dating crisis we keep talking about is actually an interpersonal skills crisis. “Relying so much on texts and DMs means we may miss out on the subtleties of face-to-face connections and diverse encounters, which may be energizing, or challenging, or a mixture of both,” says Wren.
We often blame dating apps or social media, but perhaps other forms of technology are to blame as well. We’ve spent so much of our lives communicating through texts, voice notes, and algorithms that we’ve lost the confidence to navigate the ambiguity of flirting with a stranger.
No one is born with the ability to make small talk, listen actively, or flirt. Like any skill, it becomes stronger through practice, and in that way we start to develop our own style of interacting with others.
However, while people had more opportunities to interact with strangers in the past, bars, workplaces, events, and public transport remain crucial sites for dating and flirting. But armed with weaker interpersonal skills and the heightened self-awareness of the social media age, many people feel an overwhelming pressure to carefully manage how they are perceived. My theory: all of this makes us more reluctant to meet new people and risk feeling vulnerable, rejected, or embarrassed.
It takes a lot of courage and a healthy mindset to know that rejection isn’t always a reflection of us personally. Gradual exposure is key. For example, start slowly by complimenting and thanking the barista who is serving your coffee. Make eye contact and smile at a stranger. Say “Good morning” or chat to someone in class or at work. Strike up a conversation with a colleague you might not know super well. Approaching someone romantically can begin to feel less intimidating the more we get used to experiencing positive interactions with people in general.
Self-compassion and self-acceptance are also important. Flirting, and dating in general, requires stepping into our vulnerability, knowing we can retreat if we feel we would like to. We have to become comfortable with uncertainty and the possibility of rejection.
As a personal experiment, I have stopped wearing headphones during my commutes and tried making eye contact and smiling at strangers. A few weeks later, while on vacation, I was at the beach and noticed a man who was looking in my direction and smiling.
A previous version of me would have ignored it and buried my head into my phone. But I smiled back and he came over to say hi. It didn’t lead to anything romantic, but I’m proud of myself for being approachable, rather than hiding.
And the experience served as a great reminder for something many of us have forgotten: flirting feels good.