Broken down, a first date is a rather unusual exercise. You’re meeting a stranger with the possibility of a relationship in the background, while trying to behave as though you’re simply having dinner.

First Dates: Create the Conditions for Connection

One of the biggest mistakes people make on a first date is trying too hard to make it go well. They arrive with questions prepared, stories rehearsed, and an unspoken pressure to work out whether this is their forever person. A social encounter quickly becomes an exercise in due diligence.

The instinct is logical: if you’re trying to make a good decision, more information should help. But the reality is rather exhausting and, more importantly, rather dull.

If you’ve met through Ivy Relations, the groundwork has already been done. You know about their work, background, interests, values and intentions. The date is where that information gives way to the experience of the person. That’s why the setting matters.

A gallery, a food market, a walk through an unfamiliar part of the city, or somewhere you’ve both wanted to try gives you something to live through together. It takes some of the weight off the conversation and creates opportunities for the sort of exchanges that can’t be planned.

Let the conversation wander

A subject comes up that neither of you expected. Someone disagrees with the other over something relatively insignificant. One story prompts another. You discover an unexpected shared interest, or a completely different point of view. These moments can be more revealing than an interview, precisely because neither person prepared for them.

Resist making an early judgement

The beginning of a date is rarely representative. You’re both slightly self-conscious. Both finding your rhythm. Even a confident person can sound less articulate than usual when they’re concentrating on making a good impression. Give some time to settle in before you start the evaluation.

Choose curiosity over the checklist

If they tell you about something they’re passionate about, don’t rush to the next question. Stay there. Ask what they love about it. What drew them to it. Why it matters. That’s where you begin to truly understand someone, rather than simply know things about them. You don’t need to come away from a first date having made a decision. You only need to know whether you’d like another conversation.


Words by Katy Pannocchia

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