To flirt without being creepy, begin with a friendly, low-pressure conversation, notice whether she chooses to participate and give her an easy way to end the exchange. Make compliments appropriate to the setting, avoid sexual remarks or unexpected touching, and stop immediately if she looks uncomfortable or says she's not interested. Good flirting feels enjoyable to both people. If only one person is enjoying it, the gentleman needs to change course.
There are men who believe flirting is a contest of persistence.
They approach a woman, deliver a line she clearly dislikes, and decide the sensible next move is to deliver another line, only louder.
This is not seduction. It is a man treating somebody else's evening as an obstacle course.
I witnessed a particularly unfortunate incident at a gallery opening, where a chap in a shiny jacket informed a woman that she had “the most dangerous eyes in London”.
She gave him a polite smile and turned back to the painting.
He followed her to the next room.
“My dear fellow,” I thought, “you've mistaken an exit for an invitation.”
Now, Monty adores a little cheek. A delightful compliment, a wicked observation, a smile held for just the right moment — all perfectly splendid.
But a gentleman must know the difference between a spark that is being shared and one he's trying to strike against a brick wall.
Start with the situation, not her body
Suppose you meet a woman at a friend's party. There's a perfectly natural reason to speak: the host, the music, the extraordinary birthday cake or the fact that everybody seems to be arguing about whether the dog is allowed on the sofa.
Try an ordinary greeting and a question.
“I'm Monty. How do you know Clara?”
That's hardly a scandalous opening. It works because she can answer briefly or join in.
At a gallery you might say, “What do you make of this? I'm fairly certain the artist is having a joke at my expense.”
She can laugh, offer an opinion or turn back to the painting. Any of those is an answer.
Compare that with telling a stranger you'd like to kiss her before you've exchanged names.
The first invitation treats her as an interesting person. The second assumes an intimacy that may not exist.
You can find somebody attractive without making her responsible for hearing every thought it inspires.
Give her an easy way out
This may be the most useful rule in the whole business.
Good flirting never makes somebody feel trapped.
At a party, you can speak for a moment and say, “I've enjoyed that. I'll leave you to enjoy the party.” If she's keen, she may continue the conversation herself.
If you're talking at a bar and she's repeatedly looking towards the person she's waiting for, don't position yourself between her and the door.
If she's working — serving your coffee, selling tickets, helping at a reception desk — remember that being pleasant is part of her job. She may be unable to leave or express disinterest as freely as someone at a party.
In those situations, keep the exchange ordinary rather than pressuring her for a number or an explanation.
You may be a magnificent specimen of masculine charm, but she is still entitled to finish her shift.
The ability to walk away graciously is not a defeat. It is a sign that you understand the invitation belongs to both people.
Learn the difference between politeness and participation
The shiny-jacketed gentleman from the gallery believed the woman had encouraged him because she'd smiled.
People smile for many reasons. Sometimes they are being friendly. Sometimes they are trying to move past a conversation without causing offence.
Look at what happens next.
Does she ask questions? Offer her own observations? Stay when she could comfortably leave? Join in the joke? Suggest continuing the conversation?
Those can be encouraging signs. None guarantees romantic interest.
On the other hand, if she's giving brief answers, looking away, moving towards somebody else or saying she needs to go, stop flirting. You do not need a committee to interpret a clear departure.
If you're uncertain, ease the intensity and let her choose whether to continue.
A gentleman cannot read minds. He can, however, recognise that a woman walking briskly towards the exit is unlikely to be requesting a second monologue.
Make compliments about what you've actually noticed
“You have a wonderful laugh.”
“I like your sense of humour.”
“That's a brilliant coat — you certainly know how to make an entrance.”
Compliments like these can feel warm when they suit the moment and aren't delivered as demands.
But avoid piling on praise until she has to manage it.
A stranger doesn't need a detailed assessment of her figure, nor an unsolicited discussion of which part of her body you find most alluring. Save intimate remarks for a relationship in which that kind of talk is mutually welcome.
Even an innocent compliment may land badly if the timing is wrong.
At the gallery, a simple “You've made that painting sound much more interesting than I thought” would have acknowledged something the woman said. It might have led to conversation if she wanted it.
Instead, our shiny gentleman persisted with an extraordinary speech about her eyes, ignoring her actual opinion of the art.
A compliment is supposed to be a gift. Don't make her sign a receipt.
How playful teasing can work — and how it goes wrong
Monty is a fervent believer in the pleasure of a little banter.
If you and a woman are discussing rival football clubs, and she's laughing at your dramatic complaints about your own team's defending, a small joke may be perfectly welcome.
“You support them voluntarily? Good heavens. You're braver than I imagined.”
But teasing works when both people are free to tease back and neither feels diminished.
Don't mock her appearance, accent, age, work, intelligence or something personal she's shared in trust. If she stops laughing, don't insist that she lacks a sense of humour.
And never treat “I was only joking” as a permission slip to say something hurtful a second time.
A good joke builds a little partnership between the two of you. A bad one leaves a woman wondering why a stranger has decided to make her the entertainment.
You can be cheeky without becoming cruel. Indeed, the former is vastly more charming.
Touching is not a shortcut to chemistry
There is a particularly tiresome corner of the dating world that recommends carefully timed touches as though women are machines operated by secret buttons.
Monty declines to subscribe.
Physical affection should be wanted by both people. If you don't know whether a touch, hug or kiss would be welcome, ask or keep your hands to yourself.
Don't assume that a woman laughing at a joke grants permission to put your arm around her. Don't keep moving closer when she's moving away. And don't treat a first date as an entitlement to physical contact.
A relaxed conversation may develop into romantic closeness. If it does, that should be enjoyable for both of you.
Sometimes the most attractive act is simply allowing a moment to remain pleasant instead of rushing to make it physical.
That leaves room for genuine anticipation, which is a far more interesting companion than pressure.
Flirting by message without crossing the line
An app match is a possible conversation, not a licence for explicit messages.
Read her profile, comment on something specific and give her room to respond. If the exchange becomes playful, follow her lead rather than abruptly introducing sexual remarks or requests for intimate photographs.
“You've made an excellent case for that little Italian restaurant. Fancy going there together?”
That's a clear invitation.
“You're so gorgeous I bet you get this every day” tells her almost nothing about you.
And if she doesn't answer, don't pursue her across another app or social platform. Don't send a series of increasingly annoyed messages demanding to know why she's quiet.
If the connection has gone cold, let it go. A woman's attention is something she chooses to give, not an unpaid debt.
When communication does continue, be open about your intentions and allow her to decide when she's comfortable meeting.
When to ask for her number — and when not to
Perhaps you've enjoyed a conversation at a party. She seems engaged, she's asked about you and you've been laughing together.
You can say, “I've enjoyed this conversation. Shall we exchange numbers and continue it over coffee?”
If she'd rather not, the answer is no. You needn't request an explanation or persuade her that you're a thoroughly decent chap.
Offering your number can sometimes be a gentler option when appropriate: “If meeting for coffee appeals, you can have my number and decide whether to call.” She can choose whether to use it.
Don't obtain her details from a workplace directory, a mutual friend or a social account after she's declined to share them. Finding the information is not the same as being invited to contact her.
The romantic art lies partly in leaving somebody free to be interested.
If you have to engineer a way around her refusal, the flirting stopped being mutual quite some time ago.
A little scene at the gallery
By the end of the evening the woman our shiny-jacketed hero had pursued was speaking with a friend near the cloakroom.
Another gentleman approached them.
He asked whether they'd enjoyed the exhibition. The women joked about a sculpture that looked suspiciously like a broken kitchen appliance. He told them he'd mistaken it for a coat stand and they all laughed.
Then he said, “I shall leave you to your evening. Lovely chatting.”
One of the women asked whether he was going to the next opening.
He told her he hoped so.
Nothing forced. Nothing theatrical. Just a conversation in which the participants seemed pleased to be there.
They might never see one another again. That possibility doesn't make the exchange unsuccessful.
What if you misjudge the moment?
You might make a joke that lands badly or offer a compliment she doesn't enjoy.
If you realise you've made her uncomfortable, acknowledge it briefly: “Sorry, that was too personal. I shouldn't have said it.”
Then stop doing the thing that caused the problem.
Don't demand that she reassure you. Don't explain the joke for ten minutes or insist she take it as intended.
If she wants to move away or end the conversation, let her.
People make mistakes. What matters is whether you respond respectfully rather than defending your right to repeat them.
Likewise, if you're genuinely uncertain whether a woman is enjoying some flirtation, you can ask plainly: “Is this all right?” A considerate question is not a romantic catastrophe.
The purpose of flirting is mutual pleasure, not testing how far you can go before somebody protests.
When flirting is welcome, make it personal
Once you're sharing a lively conversation, your interest can become clearer.
“I like talking to you. You've got a wicked sense of humour.”
Or, after you've both been enjoying a little teasing: “I feel we may need a second coffee to settle this dreadful disagreement.”
She can agree, laugh or decline. The choice is hers.
What makes the moment attractive isn't the perfection of the sentence. It's that you've noticed something real, expressed genuine interest and made a confident invitation without attempting to corner her.
A good flirtation might result in a date. It might remain a delightful five-minute exchange. Either outcome is better than an evening remembered because somebody wouldn't accept a hint.
Monty's rule about knowing when to leave
I've never believed that charm consists of collecting phone numbers like medals at a county show.
Charm is the quality of an encounter. Did she enjoy herself? Did you? Did the conversation make you both smile? Would either of you genuinely like another?
Those are worth far more than a rehearsed line delivered regardless of the response.
You can be bold, playful, stylish and interested without being intrusive. In fact, knowing when to hold back often makes your interest more credible.
For a little more of my advice on making a memorable first impression and turning genuine interest into enjoyable dates, The free offer is below. Its title? 7 Secrets to Becoming a Babe Magnet.
And should you encounter the fellow in the shiny jacket, old boy, do tell him that following a woman from room to room is not called flirting. It's called needing a new hobby.