To date confidently when you are bald, present your actual appearance clearly, choose grooming and clothes that make you feel well turned out, and let the woman you meet discover the rest of your personality. Use recent photographs that show your head rather than hiding it, avoid making constant jokes at your own expense, and flirt as you would if your hairline were never part of the conversation. Baldness may matter to some women's preferences and not to others. It does not decide whether a particular woman will enjoy a date with you.
A gentleman arrives at a rather elegant cocktail party wearing a flat cap. Nothing unusual there. Except he keeps the cap on indoors, through dinner, while dancing, and eventually while explaining to a woman that he is perfectly comfortable with his appearance.
He is so comfortable, in fact, that he has appointed his flat cap the sole custodian of his entire romantic reputation.
The lady is much more interested in his joke about the host's enormous chandelier. Unfortunately, he is too busy adjusting the cap to notice.
I have nothing against hats. In the right circumstances a good hat is a splendid thing. I simply refuse to make one responsible for a man's entire romantic future.
Start with the face she is actually going to meet
Online dating can create unnecessary suspense when your pictures are years old, cropped tightly or taken with a cap pulled firmly over your head.
If you're bald now, use current photographs. A clear portrait in good light is the place to start, followed by a few images that show your interests, clothes and ordinary life.
No special deception required. No dramatic announcement either.
A profile photo isn't a contractual guarantee that everyone will fancy you. It's an introduction. Giving somebody a fair picture of who they'll meet helps the two of you discover whether there's an attraction.
Avoid filters that alter your appearance beyond recognition. And if every photo has you staring fiercely into the distance from underneath a trilby, you may be communicating more about your hat collection than yourself.
Show your face. Smile if that's how you normally smile. Wear a shirt that suits you. If one photograph captures you laughing at a garden party, it may tell her more about your company than a dozen grim portraits designed to make you look like a nightclub owner.
The best version of you is still recognisably you.
Decide how you want to wear your hair, or lack of it
There is no single approved bald-man uniform.
Some men shave their heads smoothly. Others keep a close crop, wear remaining hair in a style they enjoy or simply leave things as they are. You get to make that choice.
If you like a clean-shaven look, keep it tidy in the way that suits your skin and routine. If you prefer a short cut, choose one you can maintain without checking every reflective surface on the way to a date.
You aren't trying to produce a look that every possible date must admire. Such a hairstyle has yet to be invented, even for men with outrageous amounts of hair.
A good barber can help you decide what looks well balanced if you'd like an outside opinion. You needn't buy a cupboard of miraculous products or begin a complicated new regime merely to ask someone out.
And don't postpone your romantic life until some hypothetical day when your hairline improves. A woman who likes spending time with you will be meeting the gentleman who exists today, not a future photograph.
Make the rest of your appearance deliberate
A bald head often makes the details around it more noticeable: spectacles, the shape of a beard, a collar, a lovely jacket.
This is an opportunity to develop your style, not to disguise a flaw.
Perhaps you look terrific in a neatly fitted navy shirt. Perhaps a bit of stubble suits you, or a close shave makes you look rather dashing. If you wear glasses, choose frames you genuinely like rather than something guaranteed by an online article to make you “alpha”.
The basics are much more valuable than a reinvention. Clothes that fit, clean shoes, a comfortable outfit and a little attention to your presentation.
Our cap-wearing fellow might discover that a good blazer and an open-necked shirt already look magnificent on him. It would be a terrible shame if he missed this revelation because he spent twenty minutes selecting a hat with the required concealment properties.
Dress as a man who's pleased to be invited somewhere, not as a man trying to escape a police sketch.
When a woman first sees you on a date
You have matched online or arranged to meet through friends. You've been looking forward to it. Now you're wondering whether she'll inspect your scalp the instant you arrive.
Perhaps she notices your hair, or rather the absence of it. You will also notice something about her appearance. That's what meeting people involves.
What happens next is much more interesting.
Smile, introduce yourself and start with the conversation you've come to have. “It's lovely to meet you properly. How was your journey?” is more useful than, “Yes, I know, I'm bald.”
Nobody has asked for a medical history of your follicles.
If you took honest photographs, she already has a reasonable idea of what you look like. You don't need to apologise or explain the photograph as though you've committed a fraud.
Talk about the exhibition you both wanted to see, the café's wonderfully strange decor or her recent holiday. Look for whether the two of you enjoy one another.
The date is not an examination of your head. It's a meeting between two people with entire lives attached.
Don't turn the hairline into the main entertainment
A little self-mockery can be delightful. “Well, I save a fortune on shampoo,” might be funny once, in the right exchange.
But if every other remark returns to being bald, your date may begin to wonder whether she's allowed to be interested in anything else.
Imagine she mentions loving Italian food, and you reply, “Lucky for you, there's no hair in mine.” She admires your jacket; you explain that it distracts from your head. She asks about your work; you've found another way to mention your scalp.
Darling, let the woman eat her pasta.
If she compliments your appearance, you can accept it. “Thank you, that's very kind.” You needn't contradict her or explain why her eyes must be defective.
If you feel like making one cheerful joke, make it. Then move on to the more interesting business of attraction, wit and whether she'd like to see you again.
Your baldness is a characteristic. It needn't become your entire act.
If she prefers men with hair
Not everybody fancies the same type of man. Some women love shaved heads; some prefer long hair, curls, beards or an entirely different look.
That's how attraction works. You aren't required to persuade somebody who isn't interested to change her tastes.
If somebody says she's not interested, accept it. If she volunteers a cruel remark about your appearance, you can decide you don't wish to spend more time with her.
There is no need to deliver a fiery lecture or spend the evening demanding that she revise her preferences.
Equally, avoid assuming baldness caused a rejection unless she actually told you. You may simply have had different senses of humour, different ambitions or no romantic spark.
A man who attributes every disappointing date to his hairline can miss a much more useful question: Did we actually enjoy one another?
When a woman is interested, you can let her show that interest without requiring her to produce a detailed defence of her taste in men.
Meeting women away from the apps
At a friend's birthday, a gallery opening or a sociable class, your appearance is only one of many things people discover in an instant.
They hear your laugh. They see how you treat friends. They notice whether you tell a good story, join a joke or listen when somebody's speaking.
You might catch a woman's attention with a funny observation about the evening. You might discover you both love live music. You might admire the way she defends a ridiculous film.
Don't try to make the approach about your head.
“Have you heard this band before?” is a perfectly serviceable opening at a live gig.
“Lovely to meet you—I'm Oliver,” works at a social gathering.
If she's keen to chat, enjoy it. If not, wish her a lovely evening and continue enjoying yours. Your objective is a connection with a woman who likes your company, not a campaign to secure an approval rating for your scalp.
Confidence is easier when you let your attention fall on the person you want to know.
When someone makes a joke you don't enjoy
Friends can be surprisingly bold about a man's thinning hair. Some joke affectionately; others don't know when to stop.
You can laugh if the joke genuinely amuses you. If it doesn't, there's nothing wrong with saying, “I've heard that one often enough, thanks.”
You don't have to be the good sport in every room.
If a woman you're dating makes repeated jokes that embarrass you, tell her. “I know you're teasing, but I'd rather we left the bald jokes alone.”
A considerate person can respond to that without making a fuss.
And if you're the one doing all the joking, ask whether you're genuinely enjoying the humour or trying to get your criticism in before somebody else can.
A splendid sense of humour is attractive when it comes from enjoyment. Endless pre-emptive self-insults are rather less fun to listen to.
There are countless subjects worthy of a good joke. Monty should know; I've been accused of having a joke for every button on my waistcoat.
Flirt with what you have, not what you imagine you're missing
You may have a terrific smile, an excellent voice, beautifully chosen clothes or a way of teasing that makes somebody laugh before she realises what's happening.
Use the personality that's yours.
If she admires your style, respond with pleasure. If she makes a playful comment about your sunglasses, you may gently return the compliment. If the conversation is flowing and you'd like another meeting, ask.
“I've enjoyed tonight. Would you fancy seeing that exhibition together next weekend?”
There's nothing bald-specific about a decent invitation, and that is precisely the point.
Don't approach intimacy with the assumption that she is tolerating your looks while secretly wishing you were someone else. Find out what she wants; communicate what you want; let affection develop when it's mutual.
You are a whole man, old boy. Hair was never the complete inventory.
The mysterious vanishing cap
Our cocktail-party gentleman eventually removes his cap because the room is warm. Nothing extraordinary happens.
The chandelier remains enormous. The woman he's been speaking to asks him about the peculiar watch he inherited from his grandfather. He tells her a story that makes her laugh. Later, she suggests they meet at an exhibition.
Perhaps she'll fancy him. Perhaps they're merely very good company. But at least the evening is now about them rather than a complicated object made from tweed.
Present the actual face that will arrive on a date. Wear clothes you like. Stop apologising for the top of your head, and allow somebody to discover what lives underneath it.
And should you adore a beautifully made hat, by all means wear one. Just don't appoint it Minister for Romantic Affairs.