To flirt through eye contact, meet her gaze briefly, give a genuine smile and look away naturally. If you're already talking, look at her while she speaks and let the occasional shared glance linger just enough to feel warm rather than intense. Notice whether she seems comfortable and chooses to return your attention. If she doesn't, ease off. A look can open a conversation, old boy, but it cannot tell you for certain whether a woman wants a date.
At a theatre fundraiser last spring, I met a gentleman who thought flirting with his eyes meant remaining perfectly motionless until a woman surrendered.
His name was Peregrine. He possessed wonderful manners, a fine speaking voice and an expression of such relentless intensity that the poor woman across the interval bar began checking whether there was something on her forehead.
“Monty,” he whispered, “I'm holding eye contact.”
“My dear chap, you're holding her under observation. Blink before someone calls security.”
Peregrine had been following a romantic tutorial involving exact numbers of seconds, calculated eyebrow movements and something called a “magnetic gaze”. He had practised it in the bathroom mirror and was now deploying the technique as if attempting to open a safe.
The woman, Celia, was discussing the performance with friends. What she needed from him was ordinary human conversation, not the concentrated stare of an owl awaiting a field mouse.
Eye contact can be deliciously flirtatious. But its beauty lies in its lightness, its timing and the fact that two people can decide to share it.
First distinguish a glance from a stare
Imagine you're both waiting for drinks at a reception.
You notice a woman you find attractive. Your eyes meet. You smile briefly. She may smile back, look elsewhere or simply carry on with what she was doing.
That is a glance.
A stare is when you keep watching her after she's turned away, follow her movements around the room or behave as though she must look back because you've already invested thirty seconds in the exercise.
There's no timer that turns a glance into a guaranteed romantic signal. Different people use eye contact differently, and culture, temperament, lighting and circumstance all matter.
The simplest test is whether the attention is welcome.
If she returns a smile and chooses to look your way again, that might make a friendly hello feel natural. If she seems distracted or uncomfortable, leave it there. You're looking for an invitation to converse, not collecting evidence for the Crown.
Let a smile do some of the talking
Peregrine's other difficulty was his solemnity.
His face seemed to announce that international negotiations had entered a critical stage. He was attempting to look seductive; unfortunately, he looked as though he'd discovered an error in the theatre's annual accounts.
A genuine smile changes the meaning of a glance. It says you're pleased to notice someone.
You don't need to bare every tooth or perform a wink so vigorous it threatens your cheekbone. A small, natural smile is perfectly adequate.
Perhaps she laughs at a remark you've made. You meet her eyes as you smile too. The moment feels personal because you're enjoying the same thing.
If she's not smiling or looking back, don't keep manufacturing the expression in the hope that she'll eventually respond. Eye contact is part of the exchange, not a demand for one.
And remember, some people are perfectly friendly but dislike prolonged eye contact. You can still have a lovely conversation.
At the beginning of a conversation
Suppose you've begun chatting with a woman near the theatre's interval bar.
“Did you expect the hero to survive the first act?” she asks.
Look towards her as you answer. You might smile at the memory of a particularly disastrous stage entrance. You can glance at the book in your hand or the people passing by, then return your attention when she begins speaking.
Natural eye contact moves.
A man trying to be “confident” sometimes holds his gaze so rigidly that he barely seems to hear the answer. Another looks at the floor while issuing every sentence as a hurried apology.
Aim for the middle: attention without inspection.
If you lose the thread of what she's saying because you're counting how long you've looked into her eyes, abandon the arithmetic at once. Listen to her words.
A woman may remember an enjoyable conversation. She's much less likely to remember fondly that you followed an obscure rule about blinking at exactly the appropriate interval.
During a funny or intimate moment
Eye contact can become more flirtatious once you've already established a warm exchange.
Perhaps she's describing her catastrophically unsuccessful first attempt at skiing. You've both been laughing. When she reaches the punchline, your eyes meet and she grins.
Don't rush to fill the moment with another joke. You can smile and allow the shared amusement to settle.
Or perhaps she tells you something she cares about: a painting, a pet, a place she's loved since childhood.
Look at her while she explains. If your curiosity is real, your face usually looks more interesting without any elaborate technique at all.
A warm glance after saying, “I like the way you tell that story,” can make a compliment feel more personal.
Notice the order. The conversation created the connection. Your eyes helped express it. Staring at somebody for a prescribed period does not create the relationship on its own.
What if she looks away?
Please don't consult the internet's enormous collection of claims about the direction of a woman's gaze.
Looking down could mean shyness, a passing thought or that her shoe is pinching. Looking sideways could mean she has spotted her friend, the waiter or an exit sign.
One glance tells you very little in isolation.
Pay attention instead to what the conversation is doing. Does she willingly remain? Does she ask about you? Does she seem pleased to talk? Does she respond when you suggest another topic or a possible date?
Those broader choices are more useful than treating her eyelashes as a coded message.
If she repeatedly turns away, gives short answers or seems keen to leave, stop trying to recreate eye contact. A woman doesn't owe you a romantic explanation for looking elsewhere.
It is possible to be attentive without pretending to be psychic.
The interval bar, the missing programme and Celia
Returning to Peregrine, I decided immediate intervention was necessary.
I asked him what he actually wanted to know about Celia.
“Whether she's interested in me.”
“Have you spoken to her?”
“Not really.”
“Then I recommend words. They've had a splendid run for several thousand years.”
It turned out that Celia had dropped her theatre programme near the bar. Peregrine picked it up and handed it back.
“Thank you,” she said.
“No trouble. Was the first act what you expected?”
She laughed. “Not remotely. I thought there was going to be a murder.”
“There's still time,” he replied.
They began discussing the peculiar plot. His smile was real because the subject amused him. Hers was real because she was enjoying the exchange. Several times their eyes met while they laughed at the same observations.
He finally stopped attempting to manufacture a magnetic gaze. He had rather more interesting things to look at: the programme, her expression as she told a story, and the completely disastrous hat being worn by the gentleman at the next table.
The conversation improved immediately.
Can you flirt across a room?
Sometimes you notice somebody before you meet.
A brief exchanged glance and a smile can be a pleasant beginning, particularly at a social occasion where conversation is welcome.
If she looks again or smiles back, you might introduce yourself when a natural opportunity arises. Do so politely, without blocking her path or interrupting a private conversation.
A returned glance is not permission to invade her personal space. Neither is it proof she's single or wants to be approached. A friendly hello followed by attention to her actual response is the sensible next step.
If she looks away and continues with her friends, leave it.
There is no prize for performing increasingly elaborate facial signals from across the room. The purpose of that first spark, if there is one, is to see whether a real conversation might begin.
You cannot conduct an entire courtship by glaring handsomely past a bowl of olives.
Don't use eye contact to manufacture pressure
Some advice recommends staring, moving physically closer and deliberately withholding conversation to create “tension”.
There is a rather important difference between shared romantic anticipation and making somebody uneasy.
If she steps back, turns towards another person or stops responding warmly, give her room. Never follow a woman through a venue trying to catch her eyes again.
On an actual date, you don't need to hold her gaze while she reads the menu or listens to the waiter. Let both of you enjoy the ordinary business of being together.
And when things become more romantic, don't assume a long look gives consent for a kiss. A clear question or a genuinely mutual moment is better than an invented code.
The gentleman who respects a woman's freedom is far more charming than the one treating a glance as a signed agreement.
If you're shy, begin while listening
You might find eye contact easier when the woman is talking, because you have a purpose: understanding her.
Look towards her as she explains something. Let your expression respond. When she finishes, offer a thought or question about what she actually said.
If direct eye contact feels a little intense, look naturally around her face rather than forcing yourself to lock onto her pupils. The aim is comfortable attentiveness.
A mild smile can express interest without forcing a performance. When you enjoy her company, tell her in words as well.
“I've loved talking to you about this. Fancy carrying on over a coffee next week?”
That invitation is much more informative than any eye-contact routine. It gives her the chance to answer clearly.
Your eyes can help her see your interest. They cannot make the decision for her.
When you're already dating each other
Perhaps you've met several times and know there's mutual attraction.
Eye contact may feel more intimate because you share a history. You know her jokes. You recognise that little expression she makes when she's amused. A quiet smile across a dinner table may say plenty without a speech.
Enjoy those moments without analysing them.
If she's telling you something important, look up from your phone. If you compliment her, let her see that you mean it. If you laugh together, don't be afraid of a little shared stillness.
But people vary. Some are naturally animated and constantly looking around; some look directly into another person's face when listening. Neither style is a definitive romantic verdict.
The relationship lives in your actual behaviour towards one another, not a chart of gaze duration.
Peregrine abandons his stopwatch
By the end of the theatre evening, Peregrine had discovered that Celia adored detective stories, hated unnecessarily elaborate stage sets and had an alarming ability to guess the ending of plays.
She'd also agreed to meet him for an exhibition the following Saturday.
I should not like you to imagine the theatrical fundraiser was a controlled scientific experiment. Perhaps she'd have accepted his invitation anyway. Perhaps not.
What I can say is that he was infinitely better company once he stopped trying to stare her into submission and began enjoying their conversation.
That is the real art of flirtatious eye contact: a brief invitation, a warm response when it's returned, and the good sense to look away when it isn't.
For further assistance with those first sparks, Monty's introductory gift, 7 Secrets to Becoming a Babe Magnet, is waiting via the free-guide invitation on this page.
Now, old boy, close the stopwatch. The interval's nearly over, and I've been assured somebody finally gets murdered in Act Two.