A good first message on a dating app refers to something specific in her profile and makes replying easy. Ask about the unusual place in her photograph, her favourite weekend activity or a shared interest. Keep it friendly and short; 'Hey beautiful' on its own gives her very little to work with.
Somewhere in Britain a man has matched with an attractive woman, typed “Hey beautiful”, stared at the screen for six minutes and then asked an entire internet forum whether he should add a flame emoji.
I'm sure he's a perfectly pleasant fellow. I also suspect he's making an extraordinarily simple task more complicated than the construction of the Channel Tunnel.
A first message is not your one opportunity to demonstrate that you're Britain's funniest, sexiest, most original unmarried man. It's a little knock at the door. The woman can decide whether she'd like to answer. Your job is to give her something better to respond to than a generic greeting, without turning the exchange into a performance or a demand for attention.
And no, I will not be issuing a list of fifty magic phrases that supposedly make women reply. Women aren't vending machines. You don't insert the correct sentence and collect a date from the tray.
Read the profile before you write anything
An astonishing number of opening messages appear to have been sent without the slightest examination of the person receiving them. “Hi sexy, how's your day?” could be directed at anybody. She might be a wildlife photographer, a competitive rower or a woman who has just written a magnificent paragraph about her disastrous attempt to learn Italian. You have ignored all of it.
Look for something specific that genuinely interests you. A place you recognise, a hobby you've tried, a strong opinion about films, a picture of a dog wearing an expression of deep personal disappointment. You don't need to interrogate every detail. Find one that gives you a natural place to begin.
Say her profile mentions that she owns a very opinionated dachshund. You might write: “Your dog looks like he's in charge of household policy. Is that accurate?” It's warm, relevant and easy to answer. If she says he is, you're already talking about something she chose to share.
Compare that with “You are stunning princess.” She may appreciate a compliment. But she's been given no conversation, only an assessment of her appearance.
A good opener is smaller than you think
One observation and one easy question will often do. “That photo in Lisbon brought back memories — did you manage to find a decent place for custard tarts?” is perfectly sufficient. If you haven't been to Lisbon, don't pretend otherwise. “That market looks brilliant. Where was it?” is just as natural.
Your message should sound like something you'd say aloud. Not like a message polished by three committees, an etiquette coach and an ambitious advertising agency. Imagine sitting next to her at a friend's dinner: what would you say to open a pleasant conversation?
Avoid an enormous paragraph. You're inviting an exchange, not publishing the first instalment of your correspondence from the trenches. On the other hand, don't shorten everything to “sup” and expect her to produce sparkling conversation unaided.
The sweet spot is useful information without a performance. You noticed something. You're interested. You're giving her room to answer.
Start with a photograph, but not a body part
Photos offer all sorts of openings. A mountain path, a bookshop, a scruffy terrier, a restaurant sign, a strange-looking cake. Ask about what is happening in the photograph rather than instantly judging how she looks in it.
“Were you actually brave enough to try the zip wire, or is that a very convincing pose?” works if the picture gives you a genuine reason to ask. “Is that the Yorkshire coast? I think I've eaten chips on that very wall” offers a little of yourself too.
Don't manufacture ridiculous theories about the image to seem original. If she is standing beside a horse, you needn't write a fourteen-line screenplay about your imaginary future as professional jockeys. You're allowed to ask whether she rides.
And please don't open with an explicit sexual comment. Plenty of women receive unwanted messages of that sort, and appearing out of nowhere with one is a remarkably poor way to demonstrate that you're worth getting to know.
A prompt answer is practically an invitation
If she's written, “The best hill I'm willing to die on: Yorkshire puddings belong with every roast”, you already have the makings of a conversation. “Finally, a serious constitutional position. What about Christmas dinner?” will do nicely.
The clever part isn't the joke. It's that you're meeting her where she has already chosen to express herself. If her prompt says she loves obscure museums, ask which one surprised her. If she mentions a disastrous baking attempt, share a tiny kitchen catastrophe of your own.
A little disagreement can be playful, but don't turn the first message into an argument. “You support that football team? Disgraceful” might be funny from a man she already knows. Coming from a stranger, it may simply sound tedious. Tone is harder to hear on a screen, so keep your first bit of teasing light enough to survive without facial expressions.
If the profile gives you almost nothing, you can still be straightforward. “Hello, I'm Monty. Your photos look like you've seen more of Scotland than I have — any favourite places?” There's no disgrace in normal conversation.
Funny first messages: never force the poor joke
Humour is splendid when it sounds like you. It is uncomfortable when it sounds like the opening act of a comedian whose audience is prevented from leaving.
Try teasing an absurdly ordinary subject: the merits of pineapple on pizza, whether a Sunday lie-in counts as a hobby, the correct number of biscuits to accompany a cup of tea. Only use these if the profile gives you a reason, though. Questions recycled word for word across fifty matches soon acquire the charm of a customer satisfaction survey.
A playful opener needs an escape route. She should be able to respond seriously, joke back or change the subject. Don't make the entire exchange depend on her finding your humour brilliant.
And resist the temptation to begin with an insult disguised as flirting. Telling a woman her haircut is terrible but that you'd “date her anyway” is not cheeky confidence. It's an excellent method of making her wonder why your parents allowed you near a keyboard.
What if you genuinely have something in common?
Use it. But don't just announce, “We have so much in common!” A person who likes live music and spicy food has not necessarily found her soulmate in a man who also likes live music and spicy food. That's half the population.
Instead: “You mentioned that tiny venue in Manchester. I saw a band there last winter and the singer lost his microphone halfway through. Have you been recently?” You've shown a real connection and given her an opening. If she replies with a story, follow it rather than rushing into your next prepared statement.
You can also use a difference honestly. If she's passionate about pottery and your knowledge begins and ends with a childhood attempt to make an ashtray, say so. Genuine curiosity is a perfectly respectable way to meet somebody interesting.
The aim isn't to prove you're identical. It's to discover whether your curiosity and her enthusiasm enjoy one another's company.
The first message is not the first interview
Some men, determined to avoid small talk, begin by asking what a woman wants from marriage, whether she believes in destiny and how many children she hopes to have. These questions may matter eventually. As the first sentence to a stranger, they're rather like demanding a mortgage application before offering somebody tea.
Other men ask five questions at once. Favourite holiday? Dream career? Worst date? Star sign? Political outlook? The woman opens her messages to discover an assessment centre.
Choose one manageable subject. Let her answer. See what she asks you. If it becomes a lively exchange, there will be opportunities to discuss bigger things naturally. If it doesn't, you've spared both of you an unnecessary examination.
There's nothing wrong with being intentional about dating. There is plenty wrong with confusing intention and intensity.
Compliments can work, but they must have somewhere to go
“You've got a wonderful smile” is polite enough, but it doesn't automatically start a conversation. “That photograph of you grinning at what looks like an enormous burnt cake is tremendous. What happened?” has both warmth and somewhere to go.
If you want to be openly complimentary, say something specific and tasteful: “You've got a lovely sense of style — that jacket is excellent. Was the market in the picture as good as it looks?” There is no prize for adding “gorgeous” three times.
Remember that someone's appearance is only one possible point of connection. She may be far more pleased that you noticed her love of theatre or the ridiculous caption beneath her hiking picture. Being seen as a whole person is rather nicer than being greeted as a photograph with a chat function.
When she replies, abandon the script
Suppose you asked about the dachshund and she answers, “He's a monster. He stole the Christmas ham last year.” You now have an excellent story emerging. Ask what happened. Tell her about the pet in your life, if you have one. Don't immediately switch to “What do you do for work?” because you have been advised that question two must concern employment.
An answer changes the conversation. That's the lovely thing about one.
If she gives you a short reply, you can respond naturally once rather than assuming you're doing something wrong. Perhaps she's busy or simply not very talkative. But if every message is one word and she never seems interested in learning anything about you, don't keep hauling the exchange uphill like a broken wardrobe.
There's no obligation to manufacture chemistry alone. A decent first message creates an opportunity; it does not guarantee a conversation.
What if she doesn't answer?
Then she doesn't answer. Frustrating? Sometimes. A verdict on your worth as a man? Absolutely not. She may have stopped using the app, be talking to somebody else, be overwhelmed by messages or simply not want to chat. You don't know, and you needn't invent a dramatic explanation.
A polite follow-up can be reasonable in some circumstances, particularly where you'd already begun talking and something specific was left hanging. Repeated prompts, guilt trips or “I guess nobody likes nice guys” won't help. If there's no reply, move on.
Do not purchase an expensive feature in a panic because one woman has failed to respond. Do not send the same weary opener to fifty more women as revenge against romance. Close the app and go about your life for a bit.
The message you should actually send
Choose a detail that interests you. Make one natural observation or ask a question about it. Read the sentence aloud. If it sounds like a man speaking rather than a digital marketing campaign, send it.
There will be occasions when a marvellous opener goes nowhere. There will also be occasions when an unremarkable message starts something excellent because both people are in the mood to talk. That is the part nobody selling “guaranteed replies” likes to mention.
You don't control her answer. You control whether your approach is interesting, kind and recognisably yours.
So stop agonising over the flame emoji. If you've something to say, say it. And if your opening gambit involves a pun so tortured that it requires its own ambulance, perhaps give it one more read before pressing send.