If you're worried about your weight when dating, use honest, recent photographs, wear clothes that fit comfortably now, and choose dates you can genuinely enjoy instead of waiting for your body to change. You can express attraction, make invitations and decide whether a woman suits you exactly as you are. Don't begin every conversation by apologising for your appearance or assume that a lack of chemistry must be about your size. Different women fancy different men; give the two of you a chance to find out.
A man walks into a tailor's shop and announces that he needs a jacket for a date.
“What size are you, sir?” asks the tailor.
“Smaller by Christmas, hopefully,” the man replies.
“Very good,” says the tailor, who has heard quite enough hopeful forecasts to fill the Atlantic. “But what size are you on Saturday?”
An excellent question. Saturday is when the woman has agreed to meet you. Saturday is when you need a good jacket. And Saturday is when you're going to enjoy a date, provided you haven't talked yourself out of it by attempting to dress an imaginary future gentleman.
Monty believes in turning up beautifully. He does not believe a man should suspend his romantic life until a pair of trousers gives him permission.
The woman is meeting you, not a number
Weight can feel like the most noticeable thing about you when it's something you're unhappy with.
But a date involves two people discovering much more: humour, kindness, taste, ambition, energy, conversation, attraction and whether the evening is enjoyable.
Some women prefer slimmer men, some prefer larger men and many are interested in qualities that no clothing label records. You cannot know which woman will fancy you by guessing at the preferences of women generally.
That's why the useful question isn't, “How do I make everyone overlook my weight?”
It's, “How do I present myself honestly and meet somebody who might genuinely enjoy my company?”
You can improve your presentation and make a little effort without treating your body as an apology.
And remember you also get to choose. Is she interesting? Considerate? Funny? Do you look forward to another conversation?
Dating isn't a public vote on your figure. It's a meeting between two individuals.
Let your dating photographs tell the truth
The temptation is understandable. Perhaps there's a photograph of you from five years ago in which you look noticeably slimmer. You feel it shows you at your most attractive.
If it no longer represents how you look, don't use it as your main introduction.
Choose recent, well-lit pictures that show your face and your current appearance. Include a comfortable full-length photograph, and some images of activities you actually enjoy. A good outfit, natural expression and clear composition matter more than desperately finding a camera angle that makes part of you disappear.
Don't hide behind a group of taller friends, crop every picture at your chin or edit your shape beyond recognition.
A woman who likes your photographs should be able to recognise the man who arrives.
You needn't write a dramatic disclaimer about your weight in your profile. Nor must you describe yourself with unkind jokes before anybody has said a word.
Try showing your interests instead: the live music you love, a favourite place or something you've made. Let the images and words introduce a real personality rather than a list of things you wish were different.
Clothes: fit the fellow in the mirror today
Let us return to the tailor.
The jacket that looked wonderful three years ago now pulls at the buttons. Our gentleman plans to wear it anyway, reasoning that a fashionable stranger may mistake the strain for athletic magnificence.
Don't put yourself through that.
Choose clothes that fit your present body, feel comfortable when you sit and move, and suit the setting. The size printed on the label is private information between you and a piece of fabric.
A well-cut jacket, flattering trousers, a shirt that sits properly and clean shoes can all help you feel more comfortable. You don't need an extravagant budget. You certainly don't need to purchase an entirely new wardrobe for one first date.
If you prefer darker colours, enjoy them. If you love a bright shirt, wear it. The idea that a larger man must dress like a moving shadow is particularly silly.
Try the outfit while sitting down, not only standing in front of the mirror. A dinner date involves chairs, after all, and the ability to breathe comfortably across the table is a magnificent advantage.
Clothes should work for you, not provide a second occupation in which you spend the evening adjusting your waistband.
Pick dates for pleasure, not punishment
A woman suggests a long hill walk. You dislike long hill walks. Perhaps you would dislike them at any size.
You aren't obliged to accept an outing that makes you uncomfortable simply to demonstrate that you're sporty enough.
You can say, “I like being outdoors, but I'd prefer the botanical gardens and a coffee. What do you think?”
Or perhaps you genuinely adore hiking and would be delighted to go. Enjoy it.
Your body size doesn't prescribe your interests, abilities or idea of a good date.
An art exhibition, comedy show, café, bowling night, food market or concert can provide excellent opportunities to talk. Choose activities that suit both of you.
If seating, access, distance or clothing are practical considerations, plan accordingly without treating them as secrets too terrible to mention.
“Could we pick somewhere with comfortable seating? I'd rather stay and talk than perch on those tiny stools all evening.”
That sounds like a man contributing to a pleasant plan, not apologising for his existence.
Do not turn dinner into an explanation of your eating habits
A date at a restaurant is a chance to enjoy somebody's company over food. It is not a compulsory presentation on what you ate yesterday or what you intend to eat next month.
You can choose the dish you fancy.
If you have an ordinary preference, express it. If you'd rather share starters, ask. If she chooses something different, let her.
Avoid judging what she orders, and don't assume she's judging you. It's tempting to narrate every bite: “I know I shouldn't have this,” “I'm normally much better,” “I promise I'm changing my habits.”
Unless you've agreed to discuss that subject, she may simply want to enjoy her pasta and hear the end of your story about the holiday disaster.
A man who keeps putting his body on trial is making it difficult to attend to the woman he's actually with.
There are far more romantic topics available than the moral character of a pudding.
And if she raises food or body image in an unkind way, you can decide that conversation doesn't suit you. A date is a chance to assess someone's manners too.
When you worry she will be disappointed on arrival
If you've used recent photos and agreed on an ordinary date, you've already provided an honest introduction.
You don't need to send another message an hour beforehand saying, “Just so you know, I'm a big guy. Hope you aren't disappointed.”
If your photographs are very old or misleading, update them. That's the useful correction.
Otherwise, arrive, greet her warmly and start the conversation. She may find you attractive. She may be uncertain. You may have your own reservations about the fit between you.
None of those possibilities improves because you apologise pre-emptively.
If you feel the urge to explain your size, try paying attention to a detail about her instead. Has she mentioned an unusual hobby? Did she find the café easily? What was the best part of her week?
This isn't pretending your worries don't exist. It's refusing to make the first ten minutes of a promising meeting revolve around them.
She agreed to meet a person. Allow her to meet one.
Flirting does not require permission from the mirror
There's a particular injustice in telling yourself that you must become more attractive before you can show attraction.
You fancy the woman opposite you. She's telling a delightful story. You'd like to offer a compliment.
You can.
“That jacket is fantastic on you.”
“You've got a wonderfully wicked sense of humour.”
“I've really enjoyed spending this evening with you.”
If she responds warmly, you can keep the flirtation playful. If she doesn't, allow the exchange to remain friendly.
You needn't qualify a compliment with “Not that somebody like you would ever fancy somebody like me.” That places your private doubts between you and the very woman you want to know.
And don't decide automatically that kindness is pity. If she chooses to spend time with you, listen to what she says and look at how she behaves over time.
There's no guarantee of attraction, of course. There isn't one for anybody.
But it's perfectly possible to flirt as a larger man without conducting an apologetic commentary on your physique.
If someone is unkind about your appearance
Let's be clear: other people can have preferences. They aren't entitled to be cruel.
A woman may enjoy your company and still not want another date. That's her choice, and it's best to take it at face value.
If she comments rudely on your size, you can end the evening or say that you don't appreciate the remark. You need not stay in a conversation that is disrespectful.
There is also no obligation to spend three hours proving that weight doesn't determine worth. A short, polite goodbye is sufficient.
And if you encounter unpleasant comments on an app, you can use the platform's reporting or blocking functions where appropriate. You don't need to argue with somebody who has chosen to be nasty.
Don't retaliate by criticising her body. That makes neither of you look more appealing.
A man with self-respect can distinguish “we don't suit each other” from “you're entitled to treat me badly”. The first is a normal possibility in dating. The second is a good reason to move on.
Romance after the first date
Suppose you've enjoyed several dates and begun to feel close.
You may still worry about your appearance when the relationship becomes more affectionate. It's entirely reasonable to move at a pace that feels comfortable and to talk honestly about preferences or boundaries.
You can say, “I'd like to take this slowly,” or, “I really enjoy being close to you.”
Ask what your partner likes rather than assuming what she thinks about your body. Listen to her answer. Let the experience belong to the two of you rather than an imaginary audience examining your appearance.
You don't have to insist you're the most confident man in the room. Sometimes an ordinary moment of affection is allowed to be ordinary.
If she seems interested and you want another date, make a genuine invitation. Don't expect her to do all the romantic work because you're afraid your interest will be unwelcome.
And remember that mutual attraction includes your feelings too. You aren't there solely to discover whether you've been approved.
The tailor's actual masterpiece
Our Saturday gentleman takes the tailor's sensible advice.
He buys a jacket in the size that fits, not the size he hopes to wear at Christmas. It's a deep burgundy number with proper shoulders and a lining that makes him feel like a minor aristocrat preparing for a very enjoyable scandal.
He arrives at the restaurant. His date notices the jacket, laughs at his joke about the enormous dessert menu and tells him about her work restoring old houses.
He asks questions. She asks some back. Their conversation drifts into music and weekends away.
Perhaps there will be a second date. Perhaps not. At least he can tell whether they enjoy one another, because he's spent the evening taking part instead of fighting his own clothes.
You're entitled to dress attractively, flirt and seek a relationship in the body you have today. Be honest in your photographs, thoughtful in your plans and interested in the woman across the table.
If you fancy someone, ask her out. Don't schedule romance for an imaginary version of yourself arriving next Christmas.
And if the jacket fits beautifully, keep the tailor's number. A splendid tailor is an asset no bachelor should squander.