Sometimes, just getting to a date, after rounds of swiping, ghosting, and hoping this match transcends the pen pal stage feels like a victory in and of itself. But then what do we do? Waste all that effort splashing in the shallow end of the conversation pool, rehashing tidbits (we pretend) we didn’t already know about them from a week of stalking their Instagram. And audaciously label the date “boring.”Here’s a thought: perhaps the date wasn’t boring; it was the questions you asked. But hey, no judgment, we’re here to help you become the conversationalist your dates never saw coming. But first, let’s debunk the myth that dates are like job interviews. Your goal isn’t to sell yourself or prove your worth. Genuine connections are built on vulnerability, not resume reads. Vulnerability doesn’t mean disclosing your deepest secrets, the latest drama or competing to overshare. Instead, it’s allowing someone to see more of the real you and for you to see more of each other.
How To Keep Conversation Flowing On A Date
Finding common ground is a safe place to start: shared interests, mutual friends, and similar tastes. But this is just a warm-up. Real connection? That is the art of truly seeing and being seen. Here’s how to start elevating your “I like that too” banter.
Swap the “what” with “why”
Instead of asking, “What do you do?” ask, “Why did you choose your job?” This simple switch can turn a robotic response into a much richer narrative.
Try turning ‘fun facts’ into ‘cool stories’.
Swap facts with stories
Rather than saying, “I love reading” share the one book or author who has had the greatest impact on your life. That is how things can get really interesting, really quickly.
Try these conversation upgrades
- “What made you choose…”
- “How did that make you feel?”
- “Can you walk me through that moment when…”
- “What were you thinking when that happened?”
- “Tell me the story of…”
- “Describe the exact conversation when…”
How To Master Active Listening
Many of my clients complain about their date’s lack of questions, which prompts me to ask if this is about their ego or the connection. If the conversation flows and the vibe is great, why keep score? It’s not about being the most interesting person at the table but the most interested. So, lean into curiosity. Ask them questions encouraging them to consider what makes them tick, their triumphs and trials, and the wisdom they’ve gained along the way.
It’s Not All Verbal, Baby
Remember that your non-verbal cues speak volumes. Eye contact, open body language, and nodding along to their stories show that you’re all in. Picking up on their nonverbal cues also helps. Observing their hesitations, shifts, and leaning back or in, allows you to reflect their emotions back to them. What do you notice? Excitement, discomfort? Hesitation or surprise? This can lead to…
“You’re totally lighting up talking about this—what’s the story there?”
“That got a smile. Is there more to the story?”
“You paused there. What’s on your mind right now?”
“You’ve pulled back a bit—too much, or just gathering your thoughts?”
“You seem surprised about that. Want to chat about it or skip it?”
“This seems like a tough one for you. Do you feel comfortable sharing more?”
“You seem really proud right now. Do tell”
Make like Kirsten Dunst and Jake Gyllenhaal in the noughties and express yourself with body language.
Silence isn’t your enemy, especially when punctuated by pensive reflection or eye contact. And there’s no need to rush to fill it. Letting silences happen can be powerful, and let your date share something meaningful.
By honing your ability to connect with others, you will always have a built-in boring buffer. Everyone can be interesting, and you can help get them there. But it’s more than just a public service; it’s your time saver and relationship accelerant. Helping you get to their core in one date rather than three.
Here’s to making every date an opportunity for a meaningful connection, even if it’s a missed romantic one. in the end, isn’t that what we’re all searching for?
Sera Bozza is a dating coach and the founder of Sideswiped, offering dating coaching to help you stay upright in the world of left and right swipes. Learn more about her here.
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