What to Talk About on a Date – Free Ebook

Our initial impulse might be to pick up on
a current event, some detail of the environment

or a few impressive things about our careers.
But if a date is at heart an audition for

the emotional capacities required for the
success of a long-term relationship, the real

purpose of conversation must be to try to
understand the deep self of the other person.

We know we will be doing well if, at a certain
point, our date reflects that they’ve never

been asked so many psychologically-weighty
questions – and are we perhaps some sort

of psychotherapist in training…? Such comments
playfully reflect how comparatively surface

most chat ends up being and how unnerving
and yet delightful it can be to sense that

for once the focus of another’s interest
is firmly on the details of our souls. This

is some of what we might ask in an attempt
to take the measure of another’s deeper

self: – What has made you cry in recent
times? We’re not only concerned with what

goes well for them; we’re accepting of,
and curious about their reversals. We know

there are painful sides of life for everyone,
we’re not going to insist on levity or deny

them the right to grieve. We’ll also be
sure to tell them in turn what brings tears

to our eyes.

– What was difficult in your childhood?
Without anyone meaning for this to happen,

parents inevitably bruise and damage their
children. With a light touch, we’re trying

to get a sense of their particular take on
the drama of growing up. All of us end up

a little distorted by our experiences: over-vigilant
or too relaxed; too concerned with money or

overly indifferent to material goods; frightened
of sex or excessively decadent. They won’t

be unique in having been messed up, we’re
clear on this score, but their disturbances

will be fascinatingly specific to them. We’re
signalling that understanding their child

self will be vital to grasping how they behave
and who they are as adults. It will also lay

down a reserve of compassion at moments when
their adult selves are overwhelmed by the

dynamics of the past. – What do you regret?
Our lives are crucially defined by the roads

that weren’t taken, by the choices we bungled,
by the situations we ruminate upon in the

early hours. Because there is such a risk
of humiliation in revealing where we messed

up, if we can be a patient and compassionate
listener, we will be doing something for our

date that almost no one has ever done for
them – at least outside of a professional

therapeutic context. We will be gifting them
the honour of feeling heard for their mistakes

and of being reassured that these are just
an inevitable feature of being human; it will

be a luxury far greater than being taken to
a fancy restaurant or roof-top bar.

Fourthly – To whom would you like to go back and

apologise? An associated enquiry, this one
focuses on the guilt we accumulate as we stumble

through our lives. It’s a question that
both leaves room for confession – and offers

atonement. – What would you want someone
to forgive you for? Gently, we’re probing

at what they know is tricky in their own characters.
We aren’t brutally asking what is wrong

with them (they’d take offence). We’re
inviting them to admit to one or two ways

in which they have noticed that they can cause
difficulties for others. We’ll need to have

some examples of our own follies to confess
to straight after.

– What have your exes not understood about

you? Their past relationships are the vital
repositories of clues as to the success of

their future ones. We’re wondering how well
they can pinpoint what went wrong and whether

failure has provided them with an occasion
to learn rather than merely lament or blame.

– What would you ideally want to tell your
mother? And your father? There might be tears

at the thought. There can be so much buried
sorrow in the history we share with two people

on earth we tend to love and hate in almost
equal measure – and owe so much to. We will

listen to what parents were too brittle, too
defensive or too proud to hear. It’ll be

everything that never comes out at family
gatherings, but so badly needs to be aired.

– In what ways do you feel like a bit of
an impostor at work? We’re normalising that

we all invariably feel like we don’t entirely
measure up to what is expected of us professionally.

We’re providing a refuge for a sense of
incompetence that we take such pains to hide

from the world in normal circumstances. We’re
inviting our date, at last, to let down their

guard. Having exchanged these questions, and
others like them, over many hours, we may

feel something odd starting to happen: we
may sense ourselves falling a little in love.

The process isn’t mysterious. It’s just
that we’re getting to know one another’s

deeper selves, with all the longings, errors,
terrors, regrets, weaknesses and fears involved.

There is simply nothing more seductive than
this kind of mutual self-revelation, love

being in large part the gratitude we register
when we feel accepted and seen – as well

as the compassion we experience when another
person lets down their defences and trusts

at last that someone is going to be kind to them.

Great dates are made up of great conversations.

Our Dating Cards are designed to spark insightful and playful encounters.

Click the link on screen now to find out more.

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