To feel comfortable going to social events alone, choose a gathering you genuinely want to attend, find out how it works, arrive while conversation is easy to join, and start with people who share your reason for being there. Introduce yourself to the host or organiser, make a few short conversations rather than demanding a spectacular night, and leave when you've had enough. If you hope to meet women, treat that as a welcome possibility, not a requirement for the outing to count as a success.
There are two sorts of men at a grand charity auction. The first arrives with six friends and spends the evening talking exclusively to the six friends. The second arrives alone, admires a preposterous bronze sculpture and ends up chatting to the rather entertaining woman who has just described it as “a frightened aubergine.”
Which gentleman has had the better evening? The answer has very little to do with how many people escorted him through the door.
I have attended many glorious imaginary parties for the purpose of this illustration. And I can assure you that arriving alone does not condemn a fellow to standing beside the coat rack, guarding other people's outerwear like an unpaid valet.
The secret is not to learn the manners of a professional networker. It is to give yourself a sensible reason to be there and become pleasantly involved in what's happening.
Pick an occasion with something to do besides standing
A crowded bar where everybody already seems to know one another can be a difficult place to arrive on your own. But social events aren't all like that.
A wine-tasting evening offers wines to discuss. A book launch gives you an author and subject in common. A local live-music event presents something to watch. A cookery demonstration, language exchange, quiz night or gallery opening gives strangers a perfectly ordinary opening for conversation.
Choose an event you would enjoy even if nobody especially attractive appeared.
Suppose you're fascinated by old cars. A weekend vintage-car gathering is worth attending because you might see a gorgeous restored Jaguar. If you also meet a woman who can tell you why the carburettor is unusual, splendid. If not, you've still had the pleasure of the cars.
Avoid signing up for an activity you actively dislike solely because you imagine it will be filled with eligible women. You might encounter someone you fancy and then spend your first conversation pretending to adore pottery when you've come to regard clay as a personal enemy.
Interest makes conversation easier because the subject already exists.
Before leaving, know what sort of event it is
A quick look at the invitation or organiser's information can save you needless confusion. Is it a seated talk or a drop-in gathering? Do you need a ticket? Is there a host, reception desk or name badge? When does it actually begin?
The object isn't exhaustive reconnaissance. It's knowing what you're walking into.
If it's a small event run by someone you know, you can send a cheerful message beforehand: “Looking forward to Thursday. I'll be coming on my own—is there anything you need me to bring?”
At a public event, knowing the programme helps you choose a natural arrival time. You might attend the exhibition opening rather than appearing halfway through the speech and having to climb over twelve chairs.
Dress for the occasion. A jacket is delightful if it suits the room, but there's no need to appear in formal evening wear at a village pub quiz unless that's how the entire quiz team dresses.
And keep your own way home sorted. The ability to leave when you please makes a solo outing far more enjoyable.
Walk in as a guest, not as a missing half
A man who arrives alone sometimes announces the fact as though he's presenting an unfortunate diagnosis.
“I'm here by myself, unfortunately.”
“None of my mates could make it.”
“I know it's a bit sad coming alone.”
Why advertise an ordinary choice as a personal calamity?
You bought a ticket. You fancied the event. You came. Good.
At a private gathering, greet the host and thank them for inviting you. At a public event, smile at the person on reception and ask where things are happening.
If the room is crowded, take a moment to put away your coat and see where the action is. Perhaps there's an exhibition table, drinks area or group discussing the central activity.
You're not obliged to burst through the doors announcing, “Ladies, your evening has improved.”
Though Monty admits it would make an entrance, it might be best reserved for a theatre production about a magnificently deluded prince.
The easiest people to speak to are doing something
Consider a room where everyone appears settled in groups. Joining a tight circle of close friends halfway through a private story isn't always pleasant for either party.
Look instead for someone standing near the display, waiting for refreshments or studying the same object you are. The setting supplies an opening.
“Have you tried this one yet?”
“Is this your first time at one of these events?”
“I'm trying to decide whether that painting is brilliant or whether I've misunderstood it completely.”
These aren't tricks for interrupting unwilling strangers. They're ordinary, relevant comments. Notice whether the person seems interested in chatting.
If a woman gives a short answer and returns to her friend, don't keep pressing. If she smiles, asks what you think and makes room for a conversation, enjoy it.
You might meet a lovely retired gentleman who tells you everything about the event. That is still a good conversation. An enjoyable social life is not made exclusively of romantic leads.
If you're attending a friend's party, ask the host a simple question: “Who should I say hello to? I don't know many people here.”
A good host may introduce you to a couple of guests who enjoy similar things.
Then take responsibility for the conversation rather than clinging to your host for the next two hours.
“Sarah tells me you're restoring an old house. How's that going?”
If she answers enthusiastically, follow her interest. Share a little of your own. A real conversation requires more than nodding and waiting for a romantic opportunity.
Please don't instruct the host to identify “all the single women”. It makes ordinary people sound like exhibits in an auction catalogue.
And don't assume the woman you're introduced to is available or interested. You can enjoy her company before making any guess about romance.
If there's genuine mutual warmth and you both want to continue talking, the possibility of arranging a date may arise naturally.
Sometimes a small group is talking openly about the exhibition, band or speaker. There's room near the edge, and the discussion isn't private.
Listen for a moment before jumping in. If somebody makes eye contact or pauses, you can introduce yourself and add something related.
“I overheard you discussing the old cinema across town. I used to go there. Are they reopening it?”
Then wait. Someone may explain, laugh or invite you further into the exchange.
Don't introduce yourself by telling a ten-minute story before discovering what the group is discussing. Nor should you direct all your attention towards the most attractive woman while ignoring everybody else.
An engaging man can talk to a couple, a group of old friends or another solitary visitor without behaving as though only one person in the room matters.
That's not an elaborate dating strategy. It's simply good company.
And good company tends to make the rest of the evening much easier.
If you feel awkward at events, you may imagine that successful attendance requires ten conversations, three phone numbers and an invitation to a country house.
Good heavens. That's quite a schedule.
A satisfying evening might involve a pleasant chat with the organiser, a discussion about the music, and an amusing exchange with somebody near the refreshments.
Give each interaction room to become something—or not.
If a conversation finishes, you can say, “Lovely chatting. I'm going to have a look at the photographs.” You needn't remain because you're unsure how to leave.
Likewise, don't punish yourself for spending a few minutes simply watching the event. You are allowed to enjoy whatever you came to see.
Our charity-auction gentleman may never acquire a phone number. But perhaps he finds the painting he loves, meets a friendly group and decides to return next month.
That's an excellent foundation for social confidence, particularly if you intend to keep meeting people beyond this evening.
When you fancy a woman at the event
Suppose the woman describing the bronze sculpture as an aubergine turns out to be witty, curious and charming. You spend twenty minutes comparing the strangest art in the room.
Now you may be interested in seeing her again.
Don't assume she's single because she's attending without a companion. Don't mistake friendly conversation for a promise of romance.
You can find out through ordinary conversation whether she's interested. If you've enjoyed the exchange and the occasion suits, make a light, direct invitation.
“I've loved talking with you. There's another exhibition next weekend. Would you fancy going together?”
She can accept or decline without having to escape a performance in front of half the auction guests.
If she declines, respond pleasantly and let her enjoy the event. You haven't bought the right to her company with an entertaining opinion about bronze vegetables.
If she accepts, swap details and agree to make proper arrangements later. Don't abandon your evening to spend an hour negotiating seating plans.
What if everybody seems to be coupled up?
You'll occasionally attend a party where most people have come with partners. That doesn't mean a single man has turned up to the wrong species of gathering.
Couples can be good company. You might discover new interests, make friends or hear about other events.
Don't interrupt a private romantic moment, but don't assume that a person standing beside a partner is forbidden from enjoying ordinary conversation.
If your specific aim is to meet available women, some gatherings will be more suitable than others. A singles event might be a clearer option than a wedding-anniversary dinner.
Still, evaluate the event on what it actually offers rather than deciding the night has failed because nobody fitting your romantic hopes appeared.
People notice when someone is genuinely enjoying himself. They also notice when he's scanning the room like a man searching for a missing parcel.
Be a guest first.
The art of leaving without vanishing
One delightful advantage of attending alone is that you can choose when to leave.
If you're enjoying the evening, stay. If the music has finished, your energy is flagging or tomorrow requires an early start, go.
Thank the host if appropriate, say goodbye to those you've been chatting with, and make sure you have your coat.
If you've arranged to contact somebody, do so later in a natural way. “Lovely meeting you at the exhibition. I enjoyed our debate about that sculpture.”
You needn't send a message to everyone you met, and you certainly don't owe anyone a date because you exchanged a few jokes.
If you had a flat evening, consider whether the event itself was your sort of thing before declaring that attending alone is a hopeless enterprise.
A dull event can be dull with seventeen friends present. I've been to enough imaginary banquets to confirm the principle.
The aubergine sells for a fortune
Back at the auction, our solitary gentleman and the woman with the splendidly wicked commentary discover that the bronze vegetable sculpture has sold for an astonishing amount.
“There's hope for my cooking after all,” he says.
She laughs and tells him she runs a little ceramics studio. They chat about another exhibition and decide they'd enjoy going together.
Maybe a romance begins. Maybe it doesn't. What matters is that neither needed an escort, a script or a perfect entrance to enjoy meeting somebody.
Choose places you genuinely want to go. Get involved in what is happening. Be willing to offer conversation and equally willing to let it end. Treat a romantic possibility as a pleasant addition to a life that is already being lived.
And if you see a bronze aubergine commanding an outrageous price, call Monty before you bid. I have several urgent questions about the artist.