To meet women at social events when you're nervous, choose gatherings where conversation happens naturally, arrive with one simple opening question, and take the pressure off finding a date immediately. Speak to people generally, join activities you actually enjoy, and notice whether a woman seems pleased to keep talking. If there's mutual interest, suggest continuing the conversation or exchanging details. If there isn't, leave her in peace and enjoy the rest of the event. You don't need to charm the entire room; one comfortable conversation is an excellent start.
Monty adores a lively party. Music, interesting people, a well-stocked bar and the distant possibility of someone spilling a cocktail down a priceless tapestry: the evening practically writes itself.
But I also understand the gentleman who stands just inside the doorway, holding his ticket like an admission of guilt, wondering how everyone else appears to know precisely what to say.
A chap named Oliver once informed me that he would happily cross the Atlantic in a leaky yacht but couldn't bring himself to speak to a beautiful woman at a singles supper.
“Entirely understandable,” I told him. “The Atlantic has the decency not to ask what you do for a living.”
We devised a plan that required neither pretending to be the centre of attention nor spending the whole evening trapped beside the cheese board.
Choose the right event, not the most glamorous event
Some gatherings make meeting new people easier than others. At a loud nightclub you'll often struggle to introduce yourself without shouting into someone's ear. At a cooking class, a small exhibition opening or an organised singles evening, the surroundings provide natural starting points.
Look for an event with an activity or a shared interest. A wine tasting gives you something to discuss beyond the weather. A walking group provides scenery, pace and occasional pauses. A small board-game evening puts everyone on roughly the same footing, unless somebody is being scandalously competitive about Scrabble.
If you're attending specifically to meet single women, a well-run dating social can make intentions clearer than interrupting somebody at a general event. Just remember that attending a singles evening doesn't mean anyone there owes you flirtation or a date.
The goal is not maximum female attendance per square foot. It's a setting where you can relax enough to show some personality and where conversation is welcome.
Oliver selected a local art-and-wine evening. He liked painting. He knew the difference between a landscape and a portrait. It was a sounder choice than the glamorous rooftop party he'd previously attended, where the music made everybody's introductions sound like angry declarations at sea.
Arrive early enough to find your feet
At an organised event, find the person running it. A perfectly serviceable opening is: “Hello, it's my first time here. Is there anything I should know before we start?” They may explain where to go or how introductions happen.
You can also greet the people standing nearest to you without making a grand romantic play. “Have you been to one of these before?” is not sparkling literature, but it's human and relevant.
If an event has organised rotations, games or group activities, participate. They're built to create contact between people who haven't arrived as friends.
Have an opener that belongs to the room
Forget any memorised line that could be delivered equally well in a nightclub, a supermarket or at a funeral.
Start with what's actually happening.
At a gallery: “I'm torn between loving that picture and wondering whether I've been tricked. What do you make of it?”
At a tasting: “That's the first one I've really liked. Have you found a favourite?”
At a group walk: “I've lived nearby for years and never found this path. Do you come on these often?”
These openings give her something easy to respond to. They don't force a compliment on a stranger or announce a romantic agenda before she knows your name.
When she answers, pay attention rather than racing towards your next prepared line. If she enjoys a painting because it reminds her of her grandmother's house, there's a real conversation waiting there. Ask what the house was like. Don't immediately offer your own lecture on Dutch masters.
A good opening is a door, not a performance.
Start by being sociable with everyone
A peculiar thing happens when a man decides he must speak only to women he finds attractive. The entire room becomes a row of judges, and every conversation feels like an examination.
Try enjoying the event as a guest first. Talk to the host, the older couple discussing the wine, the chap with an outrageous bow tie, and the woman who happens to be standing beside the painting you like.
This is not a trick to make the woman you fancy jealous. It means behaving as though people are interesting even when you have no romantic plans for them.
Oliver became noticeably easier to talk to once he stopped scanning the gallery for prospective girlfriends. He helped an elderly gentleman identify a painting and ended up hearing a wonderful story about a seaside holiday in 1973. It had no direct bearing on romance.
Social warmth is attractive to some people precisely because it doesn't look like a salesman closing a deal.
How to join a conversation without barging in
Look for a natural opening. A small group discussing the exhibition may be happy to include somebody who says, “Sorry to interrupt — did I hear you mention the sculptor in the next room? I thought that one was extraordinary.”
Then pause. Let them respond.
If people make space, look towards you and answer warmly, you're probably welcome to continue. If they turn back to one another, give clipped replies or move away, don't hover. Thank them and move on.
A woman standing alone isn't automatically waiting to be approached, either. She may be enjoying a quiet moment, reading a programme or checking in with a friend. A friendly, brief comment is one thing; treating her solitude as an invitation to conduct a twenty-minute interview is another.
Give people an easy exit. “Lovely talking to you — enjoy the rest of the evening” is an excellent skill. It also happens to make later conversations far less awkward.
The difference between pleasant conversation and romantic interest
Now we've reached the question Oliver was really afraid to ask: how does a gentleman know whether the woman he's talking to might fancy him?
He doesn't know from a single smile. That's the irritatingly honest answer.
Look for voluntary participation over the course of the conversation. Is she asking about you as well as answering questions? Does she choose to keep talking when the original subject has run its course? Does she show warmth or a little playful interest that seems directed towards you?
These are encouraging possibilities, not guarantees. Some people are naturally outgoing; others are reserved. A quiet woman may be interested, and a very friendly one may simply be friendly.
If you're unsure, let the conversation develop instead of interrogating every gesture. Introduce yourself if you haven't already. Share something about your own interests. A gentle compliment on an interesting idea or a colourful choice of outfit may be welcome if the moment feels right.
And never assume that attending a singles event amounts to consent to touching, relentless flirting or sharing personal details.
When a conversation begins to sparkle
Suppose she laughs at your observation about the dreadful portrait of a nobleman, asks whether you've been to the gallery before and tells you she'd rather see the smaller exhibition upstairs.
You might say, “I was going to look at that too. Fancy heading over together?”
That's a simple invitation, and she can say yes or no without embarrassment.
If you've talked for a while and the mutual interest feels promising, you can be a little more direct: “I've had such a good time debating that painting with you. Could I buy you a coffee next week?”
Notice that neither version pretends you have certainty about her feelings. Both give her the courtesy of making a choice.
If she declines, don't ask for a written explanation. Smile, thank her for the conversation and continue enjoying your evening.
If she says yes, agree on a simple way to get in touch. There's no need to announce your intentions to half the room. The gallery is not a town hall and you are not applying for planning permission.
What if you go blank halfway through?
It happens. Even excellent company can run out of words momentarily. You do not need to fill every silence with a speech about your hobbies, salary, travel itinerary and favourite type of cufflink.
Look at what she's just said. Pick up a detail. “You mentioned you came with your sister. Is she the one who persuaded you to try this?” Or return to the shared setting: “Have you seen the room upstairs yet?”
If the conversation has genuinely reached its end, let it end gracefully. “I'm going to see what they've put in the next room. It was lovely meeting you.” You can ask to continue later if the chemistry seems mutual.
Oliver once tried to rescue an awkward pause by claiming to have a personal connection to the artist. He did. He had bought a postcard in the gift shop.
“An acquaintance of some standing,” I observed.
He laughed, relaxed and admitted he knew very little about modern painting. His companion then spent five delightful minutes explaining why she loved it. Honesty achieved what an invented pedigree couldn't.
Go alone, take a friend, or join an organised group?
Go in whatever arrangement makes it easiest to participate.
A friend can help you get through the door, provided you don't spend the entire event talking only to each other. Agree beforehand that you'll circulate and catch up later.
Going alone can also work well, especially at a structured event where other people expect to meet strangers. Choose a setting with a clear programme so you aren't dependent on finding an established group willing to absorb you.
For dating-specific events, check who they're intended for, how they operate and whether they suit your age and preferences. You don't want to discover at the door that you've bought a ticket to the Annual Gathering of Competitive Ferret Enthusiasts when you thought it was a singles supper.
Unless, of course, you fancy a ferret enthusiast. Then the evening has possibilities.
Make the evening worthwhile even without a date
This is not a consolation prize. It's the practical difference between meeting women and chasing women.
If you enjoy the activity, meet a few new people and leave knowing something you didn't know before, the evening hasn't been wasted because no telephone number appeared in your pocket.
You might decide which events you enjoy, which ones are too noisy and which conversations feel most natural to you. Next time you can choose more wisely.
Try giving yourself two realistic intentions: have three genuine conversations and, if you particularly enjoy one with a woman who seems receptive, ask whether she'd like to meet again.
And don't turn the event into a numbers game in which you approach thirty people with the same line. People aren't raffle tickets.
Oliver's second visit
Oliver went to the art evening again the following month. He remembered the organiser, recognised two people from his first visit and no longer approached the doorway as though a firing squad awaited him.
He spent part of the evening discussing an extraordinary painting with a woman named Sophie. They disagreed about whether the artist had intended it to resemble a harbour. Oliver thought it was a thunderstorm. Sophie was certain it involved a badly drawn horse.
They laughed. They visited another room. Before leaving, he asked whether she'd like to try the little café across the street another afternoon.
She said she'd like that.
There's no guarantee a similar invitation will work for you. But the method is sound: go somewhere that suits you, talk to people as people, notice whether interest develops and make a respectful invitation when it does.
If you'd like a cheeky introduction to attracting women without trying to become somebody else, Monty's free free 14-page introduction to romance guide is waiting in the free-guide offer on this page.
You don't need to own the room, old boy. Just step into it, find something worth talking about, and leave the cheese board occasionally.