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Most great first dates don’t feel electric.
They feel easy.
There’s laughter.
There’s curiosity.
There’s just enough spark to want more.
What separates a “nice” date from a great one usually isn’t chemistry alone.
It’s comfort!
Download the full PDF of the Professional Matchmaker's Guide to Dating - Issue 1
Before you’ve finished saying hello, impressions are forming.
Research from Princeton shows that people make judgments about trustworthiness and warmth extremely quickly.
“Impressions of trustworthiness can be formed within 100 milliseconds of seeing a face.” — Princeton University (Willis & Todorov)
Source: https://www.sciencedirect.com/science/article/pii/S0022103106001634
That doesn’t mean you’re stuck with a snap judgment.
It means the first few minutes matter — especially your energy.
Relaxed posture.
Natural eye contact.
Genuine smile.
Those are quiet signals of confidence.
Strong first dates don’t feel like interviews.
They feel like exploration.
Harvard research shows that asking follow-up questions increases likability.
“People who ask more follow-up questions are better liked by their conversation partners.” — Harvard Business School Working Knowledge
Source: https://www.library.hbs.edu/working-knowledge/asking-questions-can-get-you-a-better-job-or-a-second-date
That means instead of moving through checklist questions, let the conversation build naturally.
Example:
Instead of:
“So what are you looking for long term?”
Try:
“What made you decide to start dating now?”
One feels evaluative.
The other feels curious.
Curiosity builds connection.
A strong first date usually moves between:
Light humor
Personal stories
Shared experiences
A touch of future curiosity
It doesn’t stay surface-level.
But it doesn’t dive into intensity too early either.
It unfolds.
And when it unfolds naturally, people feel safe opening up a little more.
Here’s something people rarely say out loud:
We’re drawn to people who make us feel calm.
When someone:
Doesn’t rush
Doesn’t overtalk
Doesn’t overcorrect awkward pauses
It signals steadiness.
And steadiness reads as confidence.
That doesn’t mean you have to be perfect.
It means you don’t need to panic when things are quiet.
Silence isn’t failure.
It’s breathing room.
Two versions of the same moment:
Version A:
There’s a pause.
Someone jumps in quickly with a random question to avoid silence.
Version B:
There’s a pause.
Someone smiles and says, “I was just thinking about what you said earlier about traveling…”
Version B feels grounded.
Small moments shape big impressions.
Great first dates don’t end ambiguously.
If you enjoyed it, say it.
“I had a really nice time tonight.”
If you’d like to see them again:
“I’d love to do this again.”
Clear. Simple. Adult.
Ambiguity creates doubt.
Clarity creates momentum.
When first dates go sideways, it’s rarely because someone isn’t impressive.
It’s usually because they’re:
Overthinking
Trying to perform
Protecting themselves too tightly
When clients learn to:
Relax into the moment
Stay curious
Move with calm confidence
Everything changes.
Often dramatically.
How do I know if a first date is going well?
If conversation feels natural and time moves quickly, that’s usually a strong sign.
What if there’s an awkward silence?
Smile, breathe, and pivot lightly. Silence is normal.
Should I talk about past relationships?
Brief mentions are fine. Deep emotional unpacking can wait.
Is instant chemistry necessary?
Not always. Comfort often comes first.
How do I avoid sounding like I’m interviewing someone?
Follow their stories instead of moving to a new category.
When should I suggest a second date?
If it felt good, clarity in the moment is usually appreciated.
A great first date doesn’t feel like an audition.
It feels like ease.
When someone leaves thinking,
“That felt comfortable. I’d do that again.”
That’s when something real begins.
Love & Matchmaking is led by Destin Pfaff and Rachel Federoff, professional matchmakers with extensive experience working with relationship-focused clients, including public-facing work on Millionaire Matchmaker, which informs a thoughtful, discreet, and compatibility-driven approach to matchmaking.
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