our impulse when looking for what to
talk about on a date 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 then the real
purpose of conversation on a date must
be to try and understand the deep self
of the other person we know we'll be
doing it 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 kind
of therapist in training such comments
playfully reflect how comparatively
surface most chat ends up being on dates
and how unnerving and yet in the end
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 on a date
in an attempt to take the measure of
another's deeper self firstly what has
made you cry in recent times here 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 secondly
what was difficult in your childhood
without anyone meaning for this to
happen
parents inevitably bruise and damage
their children with a light touch with
this kind of question we're trying to
get a sense of our dates particular take
on the drama of growing up all of us end
up a little distorted by our experiences
in childhood over vigilant or too
relaxed too concerned with money or
overly indifferent to material goods
frightened of sex or excessively
decadent our date won't be unique and
having been messed up we've got to be
clear
on this school but their disturbances
will be fascinatingly specific to them
through our question
we're signalling that understanding
their child's 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
they're adult selves are simply
overwhelmed by the dynamics of childhood
thirdly what do you regret our lives are
crucially defined by the roads that
weren't taken by the choices we bungled
by the situation's 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'll be doing
something for our date that almost no
one has ever done for them at least
outside of professional therapy we will
be gifting them the honor a feeling
heard for their mistakes and of being
reassured that these are just an
inevitable feature of being human all
this will be a luxury far greater than
being taken to a fancy restaurant or
rooftop bar fourthly to whom would you
like to go back and apologize an
associated inquiry this one focuses on
the guilt that we accumulate as we
stumble through our lives it's a
question that both leaves room for
confession and offers atonement fifthly
what would you want someone to forgive
you for gently with this kind of
question we're probing at what they
might know is tricky in their own
characters we aren't brutally asking
what's wrong with them they take offense
we're inviting them to admit to one or
two ways in which they've noticed that
they can cause difficulties for others
we'll need to have some examples of our
own follies to confess to straight after
next what have your exes not understood
about you the other person's past
relationships are a vital repository of
clues as to the success of their future
ones with this kind of question
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 then
what would you ideally want to tell your
mother and your father there might be
tears these kinds of questions 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
with this kind of question we'll end up
listening to what parents were too
brittle to defensive or too proud to
hear it'll be the sort of thing that
never comes out at family gatherings
that so badly needs to be aired
lastly in what ways do you feel like a
bit of an impostor at work with this
question
we're normalizing that we all invariably
feel like we don't entirely measure up
to what's expected of us professionally
with this question we're providing a
refuge for a sense of incompetence that
we normally take such pains to hide from
the world 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 another
person's deeper self with all the
longings errors terrors regrets
weaknesses and fears involved and there
is simply nothing more seductive than
this kind of mutual self-revelation love
being in essence the gratitude we
register when we feel accepted and seen
as well as the compassion we experience
when another person lets down their
defenses 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
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