To feel less self-conscious when flirting, stop trying to observe yourself from the outside and pay attention to the woman you're talking with. Begin with a genuine conversation, add a little playful interest when it's welcome, and let your smile, humour and compliments sound like you rather than rehearsed lines. If a joke falls flat, simply move on. If she's not responding warmly, don't push. Flirting should feel like two people enjoying an exchange—not one man trying to watch his own performance from the balcony.
There's a perfectly absurd little trick the imagination plays on a gentleman who fancies somebody.
He speaks to a woman at a wine-tasting evening, and suddenly a second version of himself appears in his head, seated in a velvet box above the room, armed with opera glasses.
This imaginary spectator whispers, “Your smile was crooked. Your laugh came too soon. Why did you say lovely? You've said lovely three times!”
Meanwhile the real woman has just told a gloriously funny story about misreading a wine label, and our man missed the end of it because he was busy criticising his own face.
The spectator, naturally, is a dreadful conversationalist. We shall eject him from the theatre.
Notice when you've left the actual conversation
You make a teasing remark. Immediately you wonder whether it sounded flirtatious enough.
She laughs. You examine whether the laugh was sincere.
You smile. You begin wondering whether your smile seems too eager.
The evening turns into an endless commentary on a conversation that ought to be happening without commentators.
You cannot reliably know what a woman thinks by inspecting your own gestures. You can, however, notice what she actually says and whether she chooses to carry on speaking with you.
If she tells you more about herself, follow the story. If she asks about your life, answer. If she clearly wants to be elsewhere, let her go.
The useful shift is from How am I coming across? to What are we enjoying together?
That's not a command to become a solemn listening machine. You can still have a wicked sense of humour. In fact, you'll be better placed to use it because you're responding to somebody real.
The woman isn't there to grade your smile. She's there for a conversation of her own choosing.
Flirting doesn't need a special voice
Some fellows become utterly different people the instant romance enters the room.
Their normal speaking voice disappears. They lower it by three octaves, lean theatrically against a wall and begin delivering remarks that would embarrass a retired nightclub magician.
Why, dear fellow?
If you're naturally quick-witted, use your own wit. If you're warm and quietly funny, use that. If you adore eccentric observations, let the odd little observations emerge.
An ordinary remark can be flirtatious when there's already a pleasant connection.
“You've convinced me that I know absolutely nothing about wine. Shall I allow you to educate me further?”
Or, after a lively debate: “An outrageous opinion. I may have to take you for coffee and hear the full defence.”
These aren't magic incantations. They're invitations to continue something both people are enjoying.
If you're performing an entirely different personality, it's difficult to pay attention to whether you actually like her.
Your natural voice is a considerably more attractive starting point than a character you invented on the journey.
Allow playful teasing to grow from the moment
A good flirtatious exchange may begin with something you both find funny.
The woman at the wine tasting tells you she once bought an expensive bottle for its glamorous label and discovered it tasted appalling.
You say, “An important principle. Never trust a wine dressed better than either of us.”
She laughs. “So you judge the bottles by their clothes?”
“Only when they've made an effort.”
That is enough. A little shared silliness, if she enjoys it.
Don't try to follow every joke with another joke because you've decided the evening must reach a minimum level of banter. One clever exchange can be delightful. Fourteen consecutive attempts may resemble a comedy audition.
And do not tease about insecurities, body features or personal subjects she hasn't invited you to joke about.
Flirting is playful because both people can enjoy it. If she doesn't seem amused, change the subject and let the conversation settle.
Being able to read the room is sexier than insisting on finishing your material.
If your compliment comes out clumsily
You want to tell her she has a wonderful laugh. Instead, your mouth produces, “Your laugh is…very enthusiastic.”
An unusual compliment, perhaps, but scarcely an international scandal.
You might smile and say, “I meant that you have a lovely laugh. That sounded better in my head.”
Then continue talking.
Don't apologise for six minutes, explain your history of awkward compliments or ask whether she's offended unless there's a genuine reason to think she is.
Small stumbles often disappear when you allow them to disappear.
She may even find the moment rather sweet. Or she may not think about it again. You cannot control that, and there's no advantage in attempting to.
The important thing is that you've expressed sincere interest without demanding a particular response.
A woman does not have to reward a compliment with romantic attention. But neither must you treat respectful attraction as something shameful.
The difference between attention and staring
One reason flirting can feel strange is that you become unusually conscious of eye contact.
You try to maintain an impressive gaze and suddenly realise you've been looking at the woman as though she were a rare stamp.
Look at her when she speaks. Let your attention shift naturally to your drink, the room or something you're discussing. Smile when you mean it.
There is no universal number of seconds that produces attraction.
If she's comfortable looking back and continuing the exchange, lovely. If she looks away or turns to speak to somebody else, don't chase her attention.
And don't assume eye contact by itself proves interest. People look at one another for many reasons.
What matters is the wider interaction: genuine conversation, opportunities chosen freely, mutual curiosity and whether she wants to spend more time with you.
Flirtation can have warmth without an elaborate choreography of eyes, shoulders and a perfectly timed eyebrow.
Trust Monty. The eyebrow becomes exhausted.
When your flirting starts to feel like an exam
Perhaps you read an article promising three irresistible lines and now expect yourself to execute them in the correct order.
You open with one. She replies in a way the article never mentioned. You panic because the next prepared line no longer makes sense.
Discard it.
If she says she's going hiking next weekend, ask where. If she tells you she dislikes the music, perhaps suggest that she has courage to admit it in a room full of fans.
Respond to the conversation that's actually happening.
A man who is genuinely interested can be charming without carrying a secret set of instructions in his head. The most memorable remark may be an offhand comment sparked by something she says.
And if she is quiet or reserved, don't automatically assume you need to increase the flirting. There may be no romantic interest, she may be considering her answer or the setting may not suit.
A good gentleman can let an interaction remain friendly without treating that as defeat.
Here's a curious thought: when you fancy a woman, you may become so occupied with how she sees you that you forget she has her own uncertainty.
She may be hoping the conversation continues. She may be deciding whether she likes your humour. She may be perfectly comfortable and not interested romantically.
You won't know until you let the two of you interact without inventing her thoughts.
Ask something relevant. Share a view. Let her make a joke. Notice whether she's choosing to invest in the exchange.
If she's smiling, asking questions and making room for another conversation, you may enjoy a little more playful warmth. If she seems hesitant or disengaged, ease off.
Never assume that someone owes you a romantic response because you've made an effort.
The possibility of mutual attraction is delightful precisely because it is mutual, not because one person can control it.
Stop imagining a distant audience and let the woman have a voice.
Flirting at a group event has its own complications. Friends may notice that you're chatting to somebody attractive and begin grinning like schoolboys.
A man can become self-conscious about an audience that has absolutely no business supervising his romantic life.
Don't perform louder for your friends. And don't involve her in jokes she hasn't agreed to become part of.
If you're enjoying a conversation, keep it as one between the two of you. You can move a little away from a noisy group if that suits her, without dragging her into an isolated corner.
If your friends tease you afterwards, you're free to smile and change the subject. You don't have to report every detail of her words to the committee.
The woman has privacy and her own social life. Allow her both.
An enjoyable flirtation is not a trophy for display after the party.
Nor is it a tragedy if you merely have a nice conversation and part as friends.
Consider two gentlemen.
One tries to appear impossibly smooth. Every sentence is considered, every smile rehearsed and every gesture inspected.
The other tells an amusing story, loses his place, laughs and asks the woman whether she's ever had such an absurd evening.
The second fellow may be more enjoyable company because the woman can respond naturally. She doesn't need to maintain the illusion that romance is occurring between two professionally polished characters.
That doesn't mean deliberate clumsiness is appealing. Don't fake an accident or pretend to be helpless.
It simply means a conversational misfire need not be a catastrophe.
If you've genuinely interrupted or been rude, put it right. But a joke that doesn't land can be left where it fell, and a slightly awkward compliment can become a smile.
The best moments often arrive in the unplanned spaces between the ones you prepared.
From enjoyable banter to a real invitation
If the woman at the wine tasting has been laughing with you and asking about your weekend, you may begin to wonder whether she'd enjoy another conversation.
You can find out.
“I've really enjoyed talking with you. Would you fancy trying that little wine bar next Thursday?”
She might accept. She might decline. Either way, the invitation is clearer than another ten minutes of examining whether your eyebrow conveyed the correct degree of mischief.
Keep the invitation appropriate and easy to refuse. You don't need to repeat it if she says no.
If she says yes, make plans. If she says she's busy and doesn't offer another time, you can leave the decision with her.
Flirting isn't supposed to postpone a straightforward question forever.
It's meant to create space in which two people can enjoy discovering whether there's something worth pursuing.
Monty ejects the imaginary critic
Our gentleman hears the woman make another joke about the glamorous wine label. This time he catches the whole story.
He laughs, adds a remark of his own, and notices that she seems delighted to continue talking.
The velvet-box critic has nothing useful to say. Quite right. His opera glasses have been confiscated.
You don't need to make yourself fascinating by force. Listen to the woman, respond with your own humour, offer honest admiration and allow a little awkwardness to pass.
If she likes your company, the conversation may develop into something delicious. If she doesn't, you've still behaved like yourself and can enjoy the rest of the evening.
As for the imaginary spectator, I propose we make him pay full ticket price next time. He has had far too many complimentary seats.