You can date when your self-esteem is low by choosing people who treat you well, making invitations you genuinely want to make, and refusing to treat every reply or rejection as a verdict on your worth. Be honest about your interests, keep your own friendships and plans, notice whether the other person is making an effort too, and don't accept poor behaviour simply because somebody has shown you attention. You needn't wait until you feel magnificent to enjoy dating; you do need to remember that your preferences count.
A fellow I shall call Rupert receives a message from a woman he's been seeing. “I'm free Thursday. Shall we go for dinner?”
Rupert has spent the afternoon worrying that his hair is thinning, his flat is unimpressive and his life lacks the cinematic splendour of a private island. He reads her invitation and concludes that Thursday is the last opportunity she'll have to discover her terrible mistake.
The lady has suggested dinner. Rupert has somehow translated it into a threat of professional inspection.
Now, men can feel uncertain about themselves for all sorts of reasons. This isn't a piece about fixing your entire life before you may purchase a romantic pudding. It's about making sensible dating choices while your opinion of yourself is still a work in progress.
You are not asking for a favour by going on a date
Low self-esteem can quietly change the terms of courtship. Instead of wondering whether the two of you might enjoy each other, you begin thinking, How lucky am I that she's giving me a chance?
There's nothing wrong with feeling pleased. There is something wrong with behaving as though her company is a charity award and yours has no value.
If a woman accepts your invitation, she is making a choice. She may be interested, curious or simply open to discovering whether there's chemistry. You don't owe her an extravagant dinner, a new wardrobe or total agreement on every subject in exchange for that choice.
Try asking yourself two questions before any date: “What am I looking forward to discovering about her?” and “What would make the evening enjoyable for me?”
Perhaps you want someone kind and witty. Perhaps you value family, adventure or quiet evenings. These are not outrageous demands from a man who sometimes doubts himself.
They are the beginnings of a relationship between equals.
Watch out for the bargain you make in your own head
The bargain sounds like this: If I make no demands, agree to everything and never disappoint her, perhaps she'll stay.
It can take surprisingly small forms. She consistently chooses expensive venues beyond your budget; you agree and worry about the bill later. She cancels at the last minute for the fourth time; you apologise for being inconvenient. She makes a remark about your appearance that stings; you laugh because you're frightened to object.
Stop. Being agreeable isn't the same as making yourself available for poor treatment.
A charming response to the expensive restaurant is, “That place looks lovely, but it's outside what I want to spend. Shall we try the little Italian near the square instead?”
An entirely reasonable response to repeated last-minute changes is, “I'm happy to arrange something when you're sure you're free, but I can't keep holding an evening open.”
Neither sentence requires an aggressive speech about respect. You are simply showing that your time and comfort exist.
A romance founded on you never speaking up will eventually have one exhausted participant. And he will probably be paying for the wine.
Don't apologise for your biography
You might be dating after a long relationship, returning to the scene in your forties or meeting women while your career is changing. Perhaps you've never had the glamorous lifestyle that photographs on dating profiles appear to promise.
Tell the truth about your life without introducing it as a list of defects.
Instead of “I only work in a warehouse,” talk about what your job involves, what you like, and what you're working towards. Instead of “I haven't travelled much, unfortunately,” tell her about a place you genuinely hope to visit. Instead of “I'm useless at cooking,” mention the one excellent dish you've mastered and the spectacular failure that preceded it.
You're not required to market yourself like a luxury hotel. You're allowed to be interesting in ordinary ways.
And do not borrow accomplishments. A false story about owning a business may impress someone for ten minutes, but you'll need another one when she asks how your company works.
I promise you, keeping track of a fictional corporation is an exhausting way to enjoy a Wednesday evening.
Pick dates where you can actually enjoy yourself
If you already feel a little underwhelmed by your own abilities, a grand formal setting can make you even more preoccupied with appearances. You are permitted to choose somewhere that suits you.
A walk through a lively market followed by coffee might offer more natural subjects than a silent, expensive dining room. A small exhibition gives you things to discuss. A familiar café allows you to relax about the practical arrangements.
Offer a real choice: “Would you prefer a drink at the little place on King Street or a wander round the weekend market?”
Don't automatically hand over every decision. “Anywhere you like” sounds generous once. Repeated endlessly, it gives her all the planning and gives you no chance to reveal your tastes.
Of course, a comfortable venue isn't a magical charm machine. If you don't get along, you don't get along. At least you'll discover that without the additional humiliation of trying to decode which fork belongs to the starter.
Learn to accept a compliment without arguing the case
A woman says, “You have a lovely smile.”
A man feeling low about himself may respond, “No, I don't. My teeth are awful.” She says she likes his jacket. He explains it was cheap. She enjoys his sense of humour; he apologises for being boring.
My dear fellow, she is offering a compliment, not inviting you to represent the prosecution.
Try “Thank you. That's lovely of you to say.” You don't have to agree that you're the most handsome man in Britain. You can simply accept that she likes something about you.
If you suspect she's attracted to you, let her express that without demanding that she justify it. Constantly rejecting someone's positive opinion can make a pleasant exchange unexpectedly hard work.
And return a sincere compliment when one occurs to you. Not as a desperate repayment, but because admiration can travel in both directions.
A woman may like a quality that isn't the one you spend your evenings criticising in the mirror.
Do not confuse attention with affection
Some people will give you attention without offering the connection you want. A thrilling message at midnight can feel like romance when the preceding three weeks contained nothing but silence.
Look at what is actually happening.
Does she make arrangements and follow through? Does she ask about your life? Does she respect your boundaries? Is she interested in meeting at times that aren't solely convenient for her? Can you disagree without being ridiculed?
There is no universal scoring system, and relationships develop at different speeds. But repeated behaviour matters more than the occasional flattering flourish.
If the contact is inconsistent and leaves you unhappy, you can say what you'd prefer. “I enjoy seeing you, but I'm looking for something more consistent. Is that something you want too?”
She may say no. That answer will hurt less in the long run than pretending indefinitely that your needs have vanished.
Being chosen by the wrong person is not a victory.
A first date isn't an examination you must pass
When you worry that you're not enough, you may treat every pause, joke or spilled drink as evidence that the date is slipping away.
You cannot control whether somebody is attracted to you. Nor would you genuinely want a partner who liked you only because you'd performed flawlessly.
Concentrate instead on the practical purpose of an early date: find out whether conversation flows, whether you enjoy her company and whether you'd both welcome another meeting.
If you say something clumsy, put it right. If you don't understand a reference, ask. If she talks about a fascinating hobby, show curiosity. You can be engaged and considerate while still occasionally getting your words in the wrong order.
And allow yourself to assess her. Does she listen? Does she speak kindly about people who aren't present? Do you laugh at similar things? Are you curious to meet again?
This is a much better use of your attention than monitoring whether she noticed your shoes.
Keep your own life switched on
Here's a trap. You meet a woman you adore, and suddenly every plan is negotiable if she might possibly be available.
You abandon a regular Sunday with friends. You stop working on a hobby. You keep entire weekends free in case she messages. Within a fortnight you've turned your life into a waiting room decorated with phone notifications.
That doesn't make you more attractive. More importantly, it doesn't make your life very pleasant.
Continue seeing the people you care about. Keep your interests. Make room for dating without making it the only thing that matters.
If she wants to meet when you already have plans, offer an alternative. “I'd love to, but I'm out with friends Saturday. What about Sunday afternoon?”
The point isn't to play hard to get. It's to be a man whose commitments and happiness remain real even when romance is exciting.
A partner joins your life; she shouldn't have to become the entire programme.
How to handle rejection when you're already feeling small
A declined invitation can seem to confirm every unkind thought you've had about yourself. But one woman's preference can't reasonably settle your value as a person.
If she says she doesn't feel a romantic connection, accept the answer without interrogating her. A gentle, “Thanks for being straight with me. I enjoyed meeting you,” is sufficient.
Don't immediately ask whether your appearance, job, finances or personality was the deciding factor. She may not know herself, or may not wish to explain. You are not entitled to an itemised receipt.
You can be disappointed. Spend time with friends or return to something you enjoy. Then, when you're ready, decide whether you want to meet somebody else.
Don't force another date merely to prove you're desirable. And don't allow a rejection to become a reason to pursue someone who has already said no.
You are looking for mutual enthusiasm, not a verdict that can be appealed.
Recognise what a good match feels like
A promising connection should allow both people to make requests, express opinions and decline things without a performance of fear or superiority.
She might find your awful dance moves hilarious. You might admire her determination to learn another language. You're allowed to tease one another kindly, and either of you can say when a joke doesn't land.
You may still have days when you feel ordinary or unattractive. That doesn't disqualify you from a loving relationship. But neither should romance become a full-time service in which a partner must constantly persuade you that you're worthy.
Let affection be offered freely. Treat her as someone with her own feelings and choices. Keep growing as a person for reasons larger than winning approval.
The everyday dating decisions here remain yours. Your partner's job is to love you as a person, not hand out a daily certificate of worth.
Give yourself a better measure of a successful evening
Rupert eventually goes to dinner. His date tells a ridiculous story about accidentally attending the wrong wedding reception. He makes her laugh with an equally unfortunate account of a holiday booking. They disagree about whether the theatre is worth the ticket price and make plans to visit a market instead.
He returns home without knowing whether they'll fall in love.
But he did express a preference, accept a compliment, listen to someone interesting and leave the table with his dignity intact. Not a bad evening for a man who'd almost cancelled because his flat wasn't grand enough.
Dating well when your self-esteem is low isn't a matter of pretending to be a prince. It's remembering that even a thoroughly ordinary fellow gets a say in his own romantic life.
And if she suggests dinner again, do try reading the invitation as dinner. It saves an astonishing amount of trouble.