How to Prove Attractive to Someone on a Date

The goal can be stated simply enough: the overwhelming priority, when on a date with someone we like, is to persuade them to like us back.

But the simplicity of the mission masks the complexity required to achieve it. Typically, the advice focuses on externals: what to wear, when to unfurl a napkin, what to order… But such counsel, however well-meaning, is at odds with what we ourselves know about attraction: that it is profoundly focused on psychology.

However much we may deny it to friends, a date is ultimately a search for a potential long term-partner. So what really renders someone attractive on dates are signs that they are emotionally well-equipped for what good-enough long-term relationships require. The capacity to find an ideal full-bodied Chianti on a menu may be impressive, but what we’re really alert for are signs that someone is going to be a decent companion twenty years from now when we have received a difficult medical diagnosis or are feeling weepy and ashamed at the progress of our careers.

Here then are some of the things we might do to prove attractive to another person on a date:

i. Tell them that we are a bit mad

We might, in the course of the conversation, light-heartedly drop in that we’re not quite sane. Perhaps we have great difficulty getting to sleep or get very anxious in social situations. Maybe we are often deeply sad on Sunday evenings or have a painful rivalrous relationship with a sibling.

The key is that, as we reveal these vulnerabilities, we can suggest we have a mature, compassionate, unruffled relationship to them. Yes, we may be a little mad, but we are eminently sane enough to know about and be unfrightened of our follies; we have mapped them, are able to warn others of them and can protect those we love from their worst sides. What we require in a partner is not someone who is perfect, but someone with a good handle on their manifold imperfections – who can warn us of these in good time, and not act them out in ways that will ruin our lives.

It is deeply reassuring to witness vulnerability well-worn and madness confidently understood; to see someone mature enough to talk about their immaturities in an undefended and serenely curious way.

Over the long-term, every possible partner will be revealed as rather crazy in some dimension of existence or another. So what really counts is not whether or not they are psychologically complicated, but how they relate to this complexity: the degree of insight, calm, perspective and humour they can bring to bear upon it.

Conversely, there should be nothing more terrifying on a date than a person who sticks a little too aggressively to the idea that they are totally sane and entirely normal. Anyone over the age of twenty possessed of the idea that they are ‘easy to live with’ has evidently not begun to understand themselves or their impact on others. We should probably skip desert and head home early.

ii. Ask our partners how they are a bit mad

The enquiry should sound playful, natural and wholly compassionate. Having laid out our flaws of character, we should take it as a given that – despite their evident strengths and accomplishments – our date too will have a litany of their own madder sides. We should create a safe space in which we imply that it is extremely unsurprising that our date should be a bit ‘broken’ in certain areas; everyone is. We can gently enquire into what makes them in particular anxious or depressed, what was untenably difficult in their childhoods or what they in particular regret and are ashamed of. This can prove charming because what we’re ultimately looking for in love are not people who find us perfect, but people who will not flinch from the sight of our wounds. We want to be seen for who we really are and forgiven; not mistaken for someone else, idealised – and then one day condemned.

iii. Reveal we’ve been a bit lonely and sad lately

We often assume that people want to hear that things are going brilliantly for us – and that we become winning for others when we can show we’re triumphing in the world. But what really warms us to others is evidence that they share in some of the very difficulties and confusions that we are beset by in our private selves. If love involves a desire for an end to loneliness, then some of what we no longer want to be lonely with are our more melancholy dimensions that most people have no time for or interest in – and that we therefore have to take care to hide from others in a bid to look competent and strong. How seductive, therefore, to stumble on someone around whom we sense we will no longer have to be jolly in a brittle way; someone who can give us room, through their own candour, to confessions of feelings of loss and sorrow. There can be few things more charming on a date than to hear, from someone who looks extremely self-possessed and competent, that they’ve been feeling unusually isolated and very perplexed of late. They’re showing us the fertilised soil in which our love can grow.

iv. Pay some compliments

We can, understandably, get anxious at the idea of having to pay our date some compliments. The approach can feel too direct, demanding, almost sleazy. But there is an art to good compliments that starts from a different place: a recognition that most of us struggle to maintain a basic grasp on what is decent and good about us, and privately hunger to hear from someone else certain basic but psychologically-sustaining things about our characters (that sound unbelievable when we try to say them to ourselves): that we aren’t wholly stupid, that some of the things we say have value; that we are sometimes funny or perceptive and have a few qualities to contribute to the world.

We can be so worried by our own inadequacies that we forget that the person across the table will have an equally large share of them – which it lies within our power to calm. With our date, we run few risks rehearsing one or two of the reasons why we found them a decent person to invite out; we should not underestimate how deeply – in the quiet of their souls – everyone tends to hate themselves.

v. Blush

For anyone with a tendency to blush, the idea that there might be something positive about going uncontrollably red in front of another on a date can sound absurd. But however uncomfortable it may be to blush, doing so indicates a range of admirable character traits we should honour in ourselves and welcome in others. Far from a disability, blushing is a sign of virtue. It’s strong evidence that one is, almost certainly, rather a nice person. We tend to blush from a fear that something about us might bother or prove unacceptable to other people. We blush after we’ve told a joke and worry that it might have come across as inappropriate or offensive. We blush when we are concerned that something we said sounded boastful. We blush because we told a little untruth, feel ashamed and fear others immediately see through us. We blush that we may desire someone who might not feel the same way about us – and whom we really don’t want to bother.

In other words, blushing is powered by an unusually strong ethical sense. It is generated by a terror of making others uncomfortable, a horror of inconveniencing people, a distaste for seeming arrogant or entitled and an overwhelming qualm about saying anything untrue.

Excessive self-doubt can, of course, blight our lives. But blushing seems on the edge of something properly worth celebrating: a high degree of self-knowledge and an awareness of how disturbing or annoying we can be to others – an imaginative exercise that will help to keep our unappealing sides properly and fruitfully in check over the long-term future we’re auditioning for.

vi. Do something clumsy

We knock over a glass on the table; drop some food down our front or jog the bread basket off the edge of the table. It feels like a disaster but so long as we handle our own clumsiness with humour, and admit good-naturedly the scale of our own ineptitude, we can turn the situation to our advantage. We are signalling that we know that what matters isn’t simply the errors we make but how we explain and frame them to those around us. Across a lifetime, we’re going to do plenty of ridiculous things – so what counts is to be able to show at the earliest moment, as we mop up the olive oil or wipe a drop of tiramisu from a nearby oil painting, that we can handle adversities and reversals without fuss or drama; that we are modest and wise enough not to expect perfection from ourselves and will hence be able to forgive slip-ups and failures in others.

These antics and more belong to a properly rich sense of what we might need to talk about on the audition of our lives we call, with touching modesty, a date.