What to Talk About on a Date

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.

– 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 the other, 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 that we will be kind to them.

Supplementary Early Date Conversation Options

– How did your childhood leave you less than ideally equipped for life?

– Which of your friends do you envy the most?

– What do you worry about in the middle of the night?

– What kind of character trait that you don’t possess do you find attractive in others?

– What do you look for in a very close friend?

– What too often goes wrong in conversation?

– What kind of ideal extra sibling would you have wanted to have?

– Complete the sentence: When I start to like someone, I worry that…

– Complete the sentence: If I was not so shy, I would…

– Complete the sentence: If someone truly knew me, they would…

– In what respects are you still the same person you were as a child?

– What would you like to change about yourself?

– In what ways is your family especially odd?

– What are you prone to be addicted to?

– What do you fear people might say about your behind your back?

– List your top three worries in your life at the moment.

– What has been the role of money in your family?