To flirt with a woman at a party, choose a moment when conversation is welcome, introduce yourself through the people or occasion you share, and keep the first exchange light. If she seems keen to continue, ask about her, share a little humour and show personal interest. If she's occupied, gives short replies or moves away, let her enjoy the party. You don't need a dramatic approach; you need to make spending a few minutes together feel like a pleasure rather than an interruption.
Parties are glorious romantic opportunities, provided you don't treat the guest list as a catalogue.
There's music, conversation, unexpected introductions and, with luck, an assortment of miniature pastries whose contents cannot be identified without the assistance of a brave volunteer.
But a party also has its own rhythm. People arrive with friends, move between rooms, refill drinks, greet hosts, find coats and occasionally try to escape the chap who wishes to explain cryptocurrency investments over the dessert table.
The art of meeting a woman there is knowing when to join the evening and when to allow it to continue without you.
I was once invited to an elaborate masked birthday party where a fellow named Lionel decided to approach every attractive woman with precisely the same line.
“Do you believe in destiny?” he asked each one.
By his sixth attempt, several guests believed destiny was directing them towards the opposite staircase.
“Lionel,” I said, “the purpose of a party is to enjoy the company. You appear to be conducting door-to-door sales.”
He removed his elaborate mask. He began behaving like a normal guest. His prospects improved at once.
Get involved before you start flirting
If you arrive at a party alone, don't plant yourself by the entrance and scan the room for women as though waiting for a parcel.
Find your host, say hello and join the occasion. Speak to the friends you know. Introduce yourself to people you don't. Ask how they know the birthday girl or what brought them there.
This isn't elaborate preparation for romance. It's simply being a sociable guest.
A woman is more likely to enjoy an approach that grows out of a shared conversation than one that feels like a sudden inspection.
Perhaps she's standing with a group discussing a dreadful song choice. You might join with a small observation when there's a natural opening. Perhaps you're both helping the host find spare glasses. That's something to talk about.
Don't interrupt a serious conversation or march up to somebody who is clearly occupied.
The best time to speak is often when two people naturally end up beside each other, not when you decide the evening's timetable requires another romantic attempt.
Introduce yourself without performing an entrance
A straightforward beginning can be wonderfully effective.
“Hello, I'm Lionel. Were you involved in planning this magnificent circus?”
She laughs and explains she's the guest of honour's oldest school friend.
“Ah, so you're responsible for her university stories. Are any of them fit for public consumption?”
If she laughs and begins telling one, you have a conversation. If she just gives a short answer, be friendly and let the exchange rest.
You don't need to announce her beauty, recite a poem or invent an extravagant theory about her being unlike any other guest.
A woman at a party is a guest with her own evening under way.
Make it easy for her to speak with you, not difficult for her to leave.
And don't blame yourself if an opening doesn't become flirtation. Some guests are there to see their friends and have no interest in meeting a date. The party can still be enjoyable.
Joining a group without stealing the conversation
Sometimes the woman you find interesting is talking with several people.
Don't march into the middle and direct all your attention at her. That can feel uncomfortable for everybody.
Listen to the topic. Introduce yourself when the group opens up. Contribute something relevant, then allow other people to speak.
If they're discussing travel, you might ask a question of the group rather than making one woman responsible for entertaining you.
At a friend's garden party, I once witnessed a chap arrive beside four guests and immediately say to the prettiest woman, “You and I should talk somewhere private.”
Her friends looked rather startled. So did she.
A much better approach would have been to join their conversation, see whether she showed particular interest in him, and allow any one-to-one exchange to develop naturally.
Nobody needs to be whisked out of a group merely because a stranger has decided she's the romantic lead in his evening.
Use the party itself to create shared humour
Parties offer material you can't manufacture.
There's the magnificent cake listing alarmingly to one side. The man desperately trying to light a garden lantern. The host's elderly aunt dominating a game intended for children.
A small comment about the shared situation can be charming.
“I believe that cake is making a determined break for the floor.”
If she laughs and adds her own observation, you have something between you: a tiny joke belonging to the night.
You can make gentle fun of the situation without ridiculing the host or embarrassing another guest.
Avoid telling jokes at someone's expense. The woman may know them well, and even if she doesn't, cruelty is a poor introduction.
Lionel eventually discovered that asking a woman whether she'd tried the host's rather adventurous canapés produced much better conversation than questioning her belief in destiny.
The pastry might have been salmon. It might have been a particularly ambitious mushroom. The uncertainty was part of the fun.
How to make it clear you're interested in her
After a few minutes of easy conversation, you may want her to know you aren't simply discussing party food.
You can offer a warm, specific compliment.
“You've got a lovely way of telling a story.”
Or, “I've enjoyed talking with you. Your opinion of this music is rather persuasive.”
A playful observation can also work if she's joining in.
“You're clearly the authority on terrible birthday playlists. I feel I've met a specialist.”
What matters is whether she's enjoying the exchange. Does she ask about you, contribute her own jokes or stay happily when there's an easy opportunity to move on?
Those signs are encouraging, but they're not an agreement to romance. Make your interest known naturally, then allow her to choose whether to respond.
There is no prize for escalating the flirtation more quickly than the evening warrants.
Respect her friends and don't isolate her
One of the least attractive behaviours at a party is treating a woman's friends as obstacles.
She arrived with people she likes. She may want to spend most of the evening with them.
Don't repeatedly pull her aside, stand between her and a friend, or complain when she wants to rejoin her group.
If you've enjoyed a conversation, you can say, “I'll leave you to catch up with everyone. Perhaps we'll talk again later.”
If she wants to continue, she may make that clear. If not, you can return to your own friends and enjoy the celebration.
Never make a woman feel that accepting a friendly chat means surrendering her entire evening.
And if she's already dancing with somebody, talking privately or looking for a quiet moment, don't interrupt because you've been told to “be bold”.
Confidence without consideration is just noise in an expensive jacket.
What if she seems interested and the party is busy?
A busy room can make it difficult to speak.
Perhaps the music becomes louder or the guests gather for speeches. You don't need to insist on finishing your conversation immediately.
You could say, “I've really enjoyed that. Shall we carry on talking when the music calms down?”
She can agree or decline.
If you naturally find yourselves chatting again later, excellent. If she becomes absorbed in something else, leave her alone rather than following her between groups.
Some men interpret a party as a challenge to monopolise a woman's attention before another man arrives.
That's a remarkably unpleasant way to think about romance. She's not a scarce item at an auction.
You can be charming and interested without staking a claim. A woman can decide whether she wants to continue talking with you, just as you can decide whether you enjoy her company.
Lionel abandons destiny
At around ten, Lionel found himself beside a woman called Niamh in the kitchen.
She was helping the host assemble a plate of sandwiches for the guests who'd arrived late.
“Do you believe in destiny?” he began, then remembered my advice.
Instead he said, “I think the cheese ones have been disappearing at a suspicious rate.”
“I've been hiding them,” she replied.
“A criminal conspiracy. May I join it?”
She laughed and handed him a plate.
For the next ten minutes they became partners in the deeply unglamorous business of feeding people. They traded opinions about the music, swapped stories about the birthday girl and discovered that they both preferred the kitchen to the crowded dance floor.
Eventually Niamh asked whether he wanted to see the garden decorations.
Lionel followed her outside along with several other guests. This time he didn't attempt to turn the moment into a private seduction.
He simply enjoyed her company.
Should you ask for her number at the party?
If you've enjoyed talking and the interest seems mutual, a direct request can be perfectly reasonable.
“I've had a really good time talking with you. Would you fancy coffee another day?”
If she agrees, you can exchange details.
Alternatively, offering your own number gives her a comfortable choice about whether to contact you later.
Don't obtain it from the host without her permission. And don't assume that sharing a party photograph or appearing in the same social group means she's invited private messages.
If she says she's not interested, be gracious and leave it there.
You can still enjoy the rest of the night without revisiting her answer or recruiting friends to persuade her.
The hostess has laid on an entire evening of entertainment. It would be a shame to spend it sulking beside the punch bowl.
Flirting while dancing
Dancing can be delightful, but it's not compulsory.
You can ask whether she'd like to dance. If she says no, accept that. If she agrees, give her room and follow whatever level of closeness is clearly welcome.
No one is entitled to physical contact because a song has a romantic chorus.
If you're a dreadful dancer, you can admit it cheerfully. I am a magnificent dancer, naturally, though several witnesses have questioned whether the word “dancing” accurately describes the movement of my legs.
What's important is enjoying the moment rather than performing an elaborate display of masculinity.
If she wants to return to her friends or sit down, let her. A shared dance is one small part of an evening, not proof of a relationship.
When to call it an evening
Sometimes you talk, flirt, exchange a number and go home feeling rather pleased.
Sometimes you enjoy a conversation but she isn't interested in another date. Sometimes you never meet somebody you particularly fancy at all.
All three are entirely ordinary.
Don't assess a party solely by the number of romantic prospects you collected. The most attractive guest is often the one who can have a splendid evening without treating every conversation as a transaction.
Lionel and Niamh eventually arranged to meet at a Sunday food market. Whether it blossomed into anything more wasn't the point of the birthday party. They'd met, enjoyed a genuine exchange and both chosen another occasion.
That is quite enough romance for one evening of suspicious cheese sandwiches.
If you'd like Monty's advice on turning a pleasant introduction into a proper invitation, my free 7 Secrets to Becoming a Babe Magnet booklet is linked from the invitation on this page.
Now, old boy, go and thank your host. And leave a canapé for the guests who haven't arrived yet.