To approach a woman for the first time, choose a moment when she seems free to talk, offer a simple greeting connected to the situation, and see whether she wants to continue. Introduce yourself if the exchange becomes friendly, ask one genuine question and contribute something of your own. If she's busy, uninterested or trying to leave, let her. A first approach isn't a speech designed to win a woman over: it's an invitation to see whether two strangers might enjoy a conversation.
I once received a letter from a gentleman who had prepared seventeen opening lines for his first attempt at meeting a woman.
Seventeen.
There was one for a café, another for a gallery, three for railway stations and a particularly alarming one involving a complaint about the price of avocados.
Unfortunately, he hadn't included a single sentence for the moment the woman actually replied.
My correspondent, Albert, had decided to attend a charity garden party to put his research into practice. He wore a new linen jacket and carried his seventeen lines on a folded sheet of paper in his pocket.
“Monty,” he said, “what if she thinks I'm an idiot?”
“Then you'll both have learned something unusually quickly,” I replied. “But she might simply think you're a pleasant chap asking about the roses.”
My dear fellow, there is no royal warrant for speaking to a woman. You don't need a title, an international reputation or a magnificent motor car. You need a sensible moment, decent manners and enough interest in the person to listen to the answer.
First, decide whether approaching makes sense
The question isn't merely whether you find her attractive. It's whether she appears to have room for a conversation.
A woman chatting at a friend's gathering, browsing an exhibition or waiting beside you for a community event to begin may be open to a polite remark.
Someone working at a till, wearing headphones, hurrying down the street, travelling alone late at night or obviously trying to get somewhere isn't necessarily available for romantic attention.
Don't block her route, follow her or demand that she stop what she's doing. She hasn't agreed to become the centrepiece of your romantic adventure.
If the situation would make it difficult for her to leave or decline, choose another opportunity. You might be a splendid conversationalist, but the poor woman should never require a tactical escape plan to get to her bus.
This isn't timidity. It's recognising that charm begins with consideration.
Use something real as your opening
At the garden party, Albert noticed a woman admiring an extraordinarily tall rose bush.
He consulted his notes.
“Are you a florist?” he asked, rather desperately.
“No,” she replied. “I just like roses.”
The conversation could have gone somewhere perfectly pleasant. Instead, Albert panicked and asked whether she preferred supermarkets with or without loyalty cards. This was line number eleven.
There was a short silence.
“Albert,” I murmured when he returned, “you've attempted to introduce a stranger to the economic structure of grocery retail.”
A better opening would have been, “Those roses are magnificent. Have you seen the ones round the other side of the house?”
She could answer, add an observation or go back to looking at the flowers.
The key is relevance. At a book launch, discuss the book. At a party, ask how she knows the host. At a class, ask whether she's attended before. Don't manufacture a common interest that doesn't exist.
And don't confuse a polite response with a request for twenty minutes of company.
Say your name before delivering your biography
Once she seems happy to talk, introduce yourself.
“I'm Albert, by the way.”
“I'm Lucy.”
“Lovely to meet you.”
There. You've managed to enter the world of civilised conversation without a single reference to the shape of her eyes or the value of your watch.
Avoid unloading your entire personal history at once. She's unlikely to need your job title, last three holidays and reasons for ending your previous relationship before she's finished her first sentence.
Share information when it fits the exchange.
If she asks what brought you to the garden party, tell her. If she mentions a hobby, ask about it if you're genuinely interested, then offer something of your own.
Approaching someone means creating an exchange, not taking possession of the conversational microphone.
Make the next sentence a response, not another prepared line
Suppose Lucy says she comes to the garden every summer because her grandfather helped restore it.
That's the interesting thing.
Don't switch immediately to a memorised question about where she would like to travel.
“You must have known this place for years. Does it look very different now?”
Let her tell you.
If she says the pond used to be full of enormous carp, perhaps you can admit that fish and formal gardens are not subjects of your expertise. A little honest amusement can make you more approachable than an invented display of knowledge.
Ask one question at a time. Listen to its answer. Follow the detail that seems to matter to her.
And allow yourself to be interesting too. A conversation in which she answers twelve questions about her life while learning nothing about yours can feel rather like being interviewed by the parish council.
How to know whether to keep talking
You can't read her mind, but you can notice what she's choosing to do.
If she asks you questions, adds stories and remains in the conversation when she could easily move on, that's encouraging.
If she's giving brief answers, looking repeatedly towards a friend, stepping away or saying she's busy, end the exchange warmly.
“Lovely chatting. Enjoy the rest of the afternoon.”
Then go.
Don't insist that her response must mean she's shy, playing hard to get or waiting for you to prove your courage. It may simply mean she doesn't want to talk.
One of life's greatest romantic assets is a gentleman who understands the word no without needing a committee to interpret it.
You can still have a thoroughly enjoyable day after one conversation goes nowhere.
What about compliments when you first meet?
A suitable compliment can be charming. But there's no need to begin by assessing the body of a woman you've never met.
A friendly observation about her coat or an enthusiastic comment on something she's done may fit the occasion.
“That scarf is a wonderful colour.”
Or after she tells a particularly good story: “You're very funny.”
But if the first thing you say is a grand declaration of her beauty, she may reasonably feel that she's being assessed rather than met.
A compliment isn't an opening fee. You don't need to pay it before conversation is permitted.
Get to know her. When the exchange becomes warmer, a sincere personal comment is easier to receive and considerably more meaningful.
And if she doesn't respond positively, don't repeat the compliment at increasing volume.
The difference between a conversation and an approach that goes on too long
Albert's second attempt at the party was with a woman beside a table of homemade chutneys.
He began by asking which jar she'd recommend. She answered, then asked whether he'd tried the damson.
They chatted about disastrous attempts at cooking. Albert described a soup he'd once served to friends that became solid when left overnight. She laughed and told him about a Christmas pudding that had survived a fall down the stairs.
It was splendid.
Then Albert remembered that his instructions included “maintain the conversation for fifteen minutes”.
He began asking about her favourite television programmes, preferred forms of public transport and whether she considered September an underrated month.
She glanced at her watch.
“My dear Albert,” I told him later, “you'd successfully met her. Why did you then insist upon keeping her until the next geological era?”
Conversation doesn't improve merely by extending it. If there's a pleasant moment, you can offer a natural goodbye and perhaps an invitation to continue another day.
When and how to suggest a date
If you enjoy talking and she seems engaged, you can make a simple proposal.
“I've enjoyed this. Would you fancy meeting for coffee another day?”
It's direct. She knows you're interested.
Don't corner her by demanding a number before she has decided. You could offer yours so that she can choose whether to contact you.
If she agrees, excellent. Confirm a practical public location when you're making plans.
If she says no, accept it with good manners: “No problem. It's been lovely talking to you.”
You haven't failed because one woman isn't romantically interested. Nor does a yes prove you've mastered the female mind.
You've asked one person whether she'd like to meet again. That is rather a pleasant achievement on its own.
Approaching women when you're out alone
Some men fear that arriving without friends makes them look peculiar.
But attending a gallery, bookshop event, public talk or social gathering alone isn't a crime. Plenty of people do.
What matters is behaving as someone who's there to enjoy the event.
Join a group conversation when welcomed. Ask a reasonable question of the organiser. Speak to men and women without treating every interaction as a romantic examination.
If you only talk to women you find attractive, the pattern can become rather obvious, particularly when you immediately abandon a conversation that doesn't promise a date.
Be a pleasant guest first. Your romantic opportunities, if any, can emerge from genuine connections.
You'll also enjoy the event even if you don't meet anyone you fancy.
When approaching in public isn't the right idea
Some situations are poor choices however clever your opening.
Don't interrupt a woman who's clearly working under pressure, receiving professional help, caring for children or trying to find somewhere safely. Don't follow a stranger after she's walked away. Don't seek out private contact details without permission.
A casual conversation may happen in a queue, café or park, but that doesn't entitle you to continue if she isn't participating.
A woman being polite at her workplace may have less freedom to end a conversation than someone at a party. Remember that.
If you're uncertain whether a greeting will be comfortable, err on the side of keeping it ordinary and brief.
There are social events and dating gatherings designed to make introductions easier. You don't need to turn somebody else's commute into your personal romantic audition.
Albert loses his seventeen lines
By the end of the garden party, Albert had folded his instructions so many times that the paper resembled a small wounded accordion.
He saw Lucy again beside the pond. She remembered he'd asked about the roses.
“Did you find the old climbing ones?” she asked.
“Yes,” he said. “And I've decided my knowledge of gardening begins and ends with recognising a flower.”
She laughed and told him she'd once killed a cactus.
This time Albert listened. They discussed dreadful gardening experiments, then found themselves walking towards the tea tent.
Before they parted, he said he'd enjoyed talking to her and asked whether she'd fancy visiting a nearby exhibition.
She said she'd think about it.
He didn't argue, plead or offer line number fourteen. He smiled and said she'd been lovely company.
That is all a first approach must be: a decent greeting, a genuine exchange and an invitation if the moment warrants it.
The complimentary Monty welcome booklet is just below, if you fancy making your next introduction a trifle more polished.
And, old boy, do throw away the avocado speech. It was never going to end well.