Stop Trying to Win the Date

Opening

First dates come with an absurd amount of admin for two people having a drink.

What should I wear? Where should we go? Should I pay? How confident should I appear? What should I talk about? How much should I reveal? Should I text afterwards? How quickly?

Then there are the larger questions lurking behind the small ones. How do I create attraction? How do I make sure this goes well? How do I get another date?

None of this is strange. If you're about to spend an evening with a woman you find attractive, of course you want her to like you. You might change shirts three times. You might suddenly become unusually interested in whether the bar has flattering lighting. You might rehearse the answer to "So, what do you do?" in the shower.

But somewhere among all those decisions, something can quietly change. You stop wondering what it will be like to meet her and start thinking about the result you need to produce.

You start trying to win the date.

Once winning is the objective, performance makes perfect sense. There is no shortage of advice about what women supposedly want. Be confident. Don't appear too interested. Never look needy. Don't reveal too much. Establish status. Make her chase you. Wait before replying. Project the right sort of masculinity.

So you make a few adjustments. Nothing dramatic. You turn the enthusiasm down here, the nerves down there. You leave out the thing you suspect might not play well. You agree a little more readily. You make sure you seem busy, confident, relaxed and absolutely not like a man who spent 20 minutes deciding between two nearly identical shirts.

You construct the bloke you think she's most likely to want.

The idea

Now suppose you absolutely nail it.

You say the right things. You're confident. You hide your nerves. You don't reveal anything you've decided might make you less attractive. You carefully manage how interested you appear. You successfully present the version of yourself you've been told women want.

And it works.

She likes you.

She wants another date.

Brilliant.

Except you've created a problem.

She doesn't really know whether she likes you. She likes the bloke you introduced her to.

Which means you now have to bring him to date two.

If that goes well, he is probably required for date three. By date five he has become a recurring character. A few weeks later you may still be editing what you say, what you admit to caring about, how quickly you reply and how much enthusiasm you're allowed to show because the performance appears to be working and you don't want to spoil it.

The better it works, the bigger the problem becomes.

Eventually the veil slips, because nobody can keep performing indefinitely. The nerves come back. The carefully hidden interests emerge. The opinions you softened turn out to be real opinions. The supposedly effortless man turns out, inconveniently, to be a human being.

That doesn't make the original performance sinister. Most people aren't setting out to deceive anyone. They're nervous. They're insecure. They really fancy the person opposite them. They want to make a good impression. All completely understandable.

That's what makes the trap so easy to fall into. You can do it with the best intentions in the world.

But if it succeeds, two people can spend weeks becoming apparently compatible while one of them is still waiting to find out whether the other person would have liked the unedited version.

The mistake happened before either of you sat down.

The question became: Can I make her like me?

But that wasn't really what the evening was for.

The question was: Do we like each other?

That tiny change from she to we changes almost everything.

Of course you want to know whether she finds you attractive. But you're also there to notice things yourself. Do I enjoy talking to her? Does she make me laugh? Am I interested in what she thinks? Does conversation feel comfortable? Do I like how she treats the waiter? When she tells a story, do I want to hear what happens next? If someone offered us another two hours, would I want them?

And she is sitting across the table discovering her version of exactly the same things.

There is something almost comically inefficient about pretending to be somebody else in this situation. The entire point is to find out whether two people fit. If one of them is supplying inaccurate information, the test might still produce a result. It just won't tell you very much.

What changes when you look at it this way

This doesn't mean making no effort.

A date is an occasion. Dress well. Shower. Turn up on time. Choose somewhere decent. Put your phone away. Be interested. Ask questions. Tell stories. Try to make the other person have a good evening.

If you're funny, be funny. If you're enthusiastic about something, don't suddenly pretend you're too cool to care about it. If you're nervous, you don't have to announce it to the room, but nor do you need to spend the evening impersonating a man who has never doubted himself in his life.

Bring your best self. Don't put on a performance.

There is a difference between bringing the best version of yourself and inventing a different version of yourself.

The first is effort. The second is theatre.

And this isn't the useless version of "just be yourself", as though the current you arrived fully formed and must now be preserved in amber.

You can dress better. Become fitter. Get better at conversation. Develop interests. Become more confident. Learn to listen. Become more considerate. Build an interesting life. Grow up.

Those things really can change who you are. They should.

Improvement is different from performance. One changes the person you bring into the room. The other changes the person you pretend is sitting there.

Become a better version of yourself rather than a convincing version of somebody else.

There is another odd thing that happens when the objective becomes "I hope she likes me".

She becomes the judge and you become the applicant.

Now every pause feels significant. Every joke that doesn't quite land goes into evidence. And if she doesn't want another date, the result can feel less like two people discovering something and more like a verdict: you weren't good enough.

Rejection can hurt. Particularly when you really liked her. There is no clever reframing that makes that completely painless.

But incompatibility and inadequacy are not the same thing.

Put the two people back where they actually are: across a table from each other, on equal footing, both finding out.

You might meet someone attractive, funny and perfectly decent and simply not feel enough to want another date. That doesn't mean she failed. She might feel exactly the same about you. Or one of you might be keen and the other not.

Attraction isn't an award for good behaviour. Nobody owes someone a second date because they performed the first one correctly.

Which brings us back to the strange idea of winning.

A date can be successful without producing another one.

You met someone. You talked. Maybe you laughed. You learned a little about each other. And one or both of you realised there wasn't enough there to continue.

The date did what it was supposed to do.

Nobody failed. Nobody won.

And occasionally something better happens.

You leave thinking, I'd really like to see her again.

And she leaves thinking the same thing.

That isn't winning the date either.

That's two people discovering they might have something.